Citrulline (CED0001321)

Record Information
Version1.0
Creation Date2014-08-29 06:16:39 UTC
Update Date2026-05-14 16:24:20 UTC
SynCED IDCED0001321
Secondary Accession Numbers
  • CHEM003255
  • T3D4295
Identification
Common NameCitrulline
ClassSmall Molecule
Description
Citrulline is an endogenous compound with the formula C6H13N3O3 and an average molecular weight of 175.19 g/mol. It exists as a solid at room temperature. Citrulline belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. Biologically, citrulline is classified as a metabolite, a human metabolite, and a micronutrient. It acts as a biological and chemical inhibitor of nitric oxide synthase (EC 1.14.13.39). In the body, it is detected in several tissues, including the liver, kidney, intestine, bladder, prostate, placenta, epidermis, fibroblasts, myelin, nerve cells, and neurons, as well as in platelets. The compound interacts with 13 recorded protein targets, including argininosuccinate synthase (ASS1), nitric oxide synthase 3 (NOS3), and putative hydrolase DDAH2. Citrulline serves as a protective agent and a nutraceutical. Industrially, it is used as a softener and conditioner. The compound is found in 21 recorded sources across various categories. These include food, food processing and cookware—specifically the preparation of malt, vinegar, wine or sparkling wine, food preservation, and fermentation processes for beer. It is also found in household cleaning and consumer products, such as soap detergents, perfumes within detergents and soaps, tobacco product cases, tobacco smoke filters, and cigar cigarettes. Additionally, it is recorded in building and construction materials, such as stairs and ramps, and electrical and electronic equipment, including electrodes, antennas, coils, conductive bodies characterized by the conductive materials, and electrically stimulated smoking devices.
Contaminant Type
  • Amide
  • Amine
  • Animal Toxin
  • Dietary Supplement
  • Drug
  • Food Toxin
  • Metabolite
  • Micronutrient
  • Natural Compound
  • Non-Essential Amino Acid
  • Nutraceutical
  • Organic Compound
  • Supplement
Chemical Structure
Synonyms
ValueSource
(S)-2-Amino-5-ureidopentanoic acidChEBI
2-Amino-5-ureidovaleric acidChEBI
alpha-Amino-delta-ureidovaleric acidChEBI
CitChEBI
delta-UreidonorvalineChEBI
L-2-Amino-5-ureidovaleric acidChEBI
N(5)-(Aminocarbonyl)-L-ornithineChEBI
N5-(Aminocarbonyl)ornithineChEBI
N5-CarbamoylornithineChEBI
N(delta)-CarbamylornithineChEBI
(S)-2-Amino-5-ureidopentanoateGenerator
2-Amino-5-ureidovalerateGenerator
a-Amino-delta-ureidovalerateGenerator
a-Amino-delta-ureidovaleric acidGenerator
alpha-Amino-delta-ureidovalerateGenerator
Α-amino-δ-ureidovalerateGenerator
Α-amino-δ-ureidovaleric acidGenerator
Δ-ureidonorvalineGenerator
L-2-Amino-5-ureidovalerateGenerator
N(Δ)-carbamylornithineGenerator
a-Amino-δ-ureidovalerateHMDB
a-Amino-δ-ureidovaleric acidHMDB
(2S)-2-Amino-5-(carbamoylamino)pentanoateHMDB
(2S)-2-Amino-5-(carbamoylamino)pentanoic acidHMDB
(S)-2-Amino-5-(aminocarbonyl)aminopentanoateHMDB
(S)-2-Amino-5-(aminocarbonyl)aminopentanoic acidHMDB
2-Amino-5-uredovalerateHMDB
2-Amino-5-uredovaleric acidHMDB
a-Amino-D-ureidovalerateHMDB
a-Amino-D-ureidovaleric acidHMDB
alpha-Amino-gamma-ureidovalerateHMDB
alpha-Amino-gamma-ureidovaleric acidHMDB
Amino-ureidovalerateHMDB
Amino-ureidovaleric acidHMDB
CIRHMDB
CytrullineHMDB
D-UreidonorvalineHMDB
DL-CitrullineHMDB
GammaureidonorvalineHMDB
H-Cit-OHHMDB
L(+)-2-Amino-5-ureidovalerateHMDB
L(+)-2-Amino-5-ureidovaleric acidHMDB
L(+)-CitrullineHMDB
L-2-Amino-5-ureido-valerateHMDB
L-2-Amino-5-ureido-valeric acidHMDB
L-CitrullineHMDB
L-CytrullineHMDB
L-N5-Carbamoyl-ornithineHMDB
N()-CarbamylornithineHMDB
N(5)-(Aminocarbonyl)-DL-ornithineHMDB
N-CarbamylornithineHMDB
N5-(Aminocarbonyl)-L-ornithineHMDB
N5-(Aminocarbonyl)-ornithineHMDB
N5-Carbamoyl-L-ornithineHMDB
N5-CarbamylornithineHMDB
ND-CarbamylornithineHMDB
Ndelta-carbamy-ornithineHMDB
Ndelta-carbamylornithineHMDB
Ngamma-carbamylornithineHMDB
SitrullineHMDB
UreidonorvalineHMDB
UreidovalerateHMDB
Ureidovaleric acidHMDB
Chemical FormulaC6H13N3O3
Average Molecular Mass175.186 g/mol
Monoisotopic Mass175.096 g/mol
CAS Registry Number372-75-8
IUPAC Name(2S)-2-amino-5-(carbamoylamino)pentanoic acid
Traditional NameL-citrulline
SMILESN[C@@H](CCCNC(N)=O)C(O)=O
InChI IdentifierInChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1
InChI KeyRHGKLRLOHDJJDR-BYPYZUCNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-alpha-amino acids
Alternative Parents
Substituents
  • L-alpha-amino acid
  • Fatty acid
  • Isourea
  • Amino acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carboximidamide
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Primary aliphatic amine
  • Organopnictogen compound
  • Imine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue Locations
  • Bladder
  • Epidermis
  • Fibroblasts
  • Intestine
  • Kidney
  • Liver
  • Myelin
  • Nerve Cells
  • Neuron
  • Placenta
  • Platelet
  • Prostate
Applications
Biological Roles
Chemical Roles
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point235.5°C
Boiling PointNot Available
Solubility200 g/L (at 20°C)
Predicted Properties
PropertyValueSource
Water Solubility21.8 g/LALOGPS
logP-3.3ALOGPS
logP-3.9ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)2.27ChemAxon
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area118.44 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.33 m³·mol⁻¹ChemAxon
Polarizability17.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0a4i-0920000000-2d92b63cd5d9648023b8Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-9610000000-2e7cd23afc2adcef35a3Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0a4i-0920000000-2d92b63cd5d9648023b8Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-00di-9610000000-2e7cd23afc2adcef35a3Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-007o-9100000000-1f8dd2c6648b104639c7Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00dl-9410000000-37909012a777213f8566Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-4c1d7af748a47e489949Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9000000000-988fced362fc0da157c9Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9000000000-0818e0e8bcee12692498Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004j-0900000000-5fa8a338dcd2f2a6bdd2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-16763200aa07f7629ad4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-3900000000-d9cfc5187aa799f6f978Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-10ee9a593e13550bec1cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-45d272576af34c9512a3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-3900000000-6177a284fdea5a3f1306Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-d9456d45e2dbd7a3df10Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-ada57cdc73bda93be483Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-008a-0904000000-23fbe48f82e515087d68Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-5900000000-78afcbaf8b8b3eabf174Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-8fb191d4c20fd54b9282Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-da484f0362a8dca5127eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00e9-0900000000-46229b4f77feabb3f857Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-4aca1022c393602a297dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-3bc2eff2e907b7734cc8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-3900000000-2613bf40e3be814da86fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9300000000-e83287bbc060eb9cf6f3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-056r-0900000000-694a8872bdfd7eec1f2bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-08fr-2900000000-15b4711991ea9985fb2bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9300000000-915fbb73e0b728420e4aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9000000000-67e60567f5c062728350Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9000000000-25140713431edd7c5eeaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-074i-5900000000-bf58ae40ccbbcae3b59eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-daf5b8d935c6f60c6df7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00e9-0900000000-46229b4f77feabb3f857Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-4aca1022c393602a297dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-322d7f0082e7d5c6ebeeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-3900000000-2613bf40e3be814da86fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9300000000-e83287bbc060eb9cf6f3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-5900000000-78afcbaf8b8b3eabf174Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-8fb191d4c20fd54b9282Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-0900000000-da484f0362a8dca5127eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-daf5b8d935c6f60c6df7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-20fe8593ca8d8303d73aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-a2851fcef80bb0d9b984Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-056r-0900000000-694a8872bdfd7eec1f2bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-08fr-2900000000-15b4711991ea9985fb2bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9300000000-915fbb73e0b728420e4aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9000000000-67e60567f5c062728350Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9000000000-603badf565140abcd117Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-3900000000-d9cfc5187aa799f6f978Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-10ee9a593e13550bec1cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-3900000000-6177a284fdea5a3f1306Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-d9456d45e2dbd7a3df10Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0900000000-ada57cdc73bda93be483Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-074i-5900000000-bf58ae40ccbbcae3b59eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0900000000-9e195f6724ee47655efbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-0900000000-1742c58acfb2cc3f3944Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9000000000-79ecc9073c58ef4e4324Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0c00-2900000000-d8d80904701cc568af2fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9000000000-0360aa890d4e3a713155Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9100000000-2733671d087bffd90c02Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-1900000000-bbf095fbcf5d6c1f2dd2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002r-7900000000-189a603832f2558718fdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9300000000-3e3467dd364b5a0f1b03Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9000000000-691b46438824fd5e967fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004r-9500000000-5a078111ec0eca0d3e91Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9600000000-3c604e922e1a0e5d7472Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0bt9-1900000000-9c279709f6728c9a562dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0c00-3900000000-c22cc0dfc92c96c2bb4eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00dl-9000000000-d06894e2aa663d4ce491Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0bt9-1900000000-571e2b6dd0203f264c2dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-052b-0900000000-738110f00c778306cbbeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9000000000-417f31e5e0d0197e4964Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0c00-2900000000-e93c713f419bfa8c138fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-eab38a193a783828cfefNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9000000000-e4ea3ce4c0adef0aac02Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0c00-3900000000-0992386980f17a4a8c48Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a6s-0900000000-79a71f95dfc8b417601bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9300000000-c21da5371cc6c3b25e83Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-00ec617370cf818e457bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-90dccca01974dd90c87eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-1900000000-118ded80f4ea4b12df49Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-074i-9800000000-68f65ef8ab4a47869b02Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9100000000-2317f4bc3a987a435712Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-e02f00db786cff0d5b64Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9200000000-898ac67f0f138673aaa8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9000000000-510b1aed3a5d8d3241e2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-3900000000-6ade556417852c8c62b0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9200000000-397f8cecaec54eef3f83Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-252782ec67bc863f2ea7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0019-1900000000-fbac319813628fc9f627Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-fa765d7c6569392360f8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000x-9100000000-8834188bea8bee0299feNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-2900000000-dcecc9946add826abeefNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-02h0-9800000000-2b60c15fc99ccb2aeb77Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9000000000-a300448ea550a2c26fa6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-008c-3900000000-156bb935b65491616bccNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001l-7900000000-edf4d07a5999823839d1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-5609661c8ad432e77256Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05xr-1900000000-1addffa6d45f8970bb87Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9300000000-43c77c654e7b19dc7355Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00di-9000000000-37c27f0534146cfc2772Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0089-0900000000-fc6232218e6492527c73Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01q9-2900000000-8d873455742869882e96Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-c4503bf7e22592041d5aNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, H2O, experimental)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Toxicity Values
Toxicity ValueOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalToxicity RatingReference
6508.0 Log mg/kg [3700:12000]RatLD50oralpredictedNot AvailableNot Available
Toxicity / Toxin ClassNot Available
Mechanism of ToxicityL-citrulline is converted to L-arginine by argininosuccinate synthase. L-arginine is in turn responsible for citrulline's therapeutic affects. Many of L-arginine's activities, including its possible anti-atherogenic actions, may be accounted for by its role as the precursor to nitric oxide or NO. NO is produced by all tissues of the body and plays very important roles in the cardiovascular system, immune system and nervous system. NO is formed from L-arginine via the enzyme nitric oxide synthase or synthetase (NOS), and the effects of NO are mainly mediated by 3',5' -cyclic guanylate or cyclic GMP. NO activates the enzyme guanylate cyclase, which catalyzes the synthesis of cyclic GMP from guanosine triphosphate or GTP. Cyclic GMP is converted to guanylic acid via the enzyme cyclic GMP phosphodiesterase.

NOS is a heme-containing enzyme with some sequences similar to cytochrome P-450 reductase. Several isoforms of NOS exist, two of which are constitutive and one of which is inducible by immunological stimuli. The constitutive NOS found in the vascular endothelium is designated eNOS and that present in the brain, spinal cord and peripheral nervous system is designated nNOS. The form of NOS induced by immunological or inflammatory stimuli is known as iNOS. iNOS may be expressed constitutively in select tissues such as lung epithelium.

All the nitric oxide synthases use NADPH (reduced nicotinamide adenine dinucleotide phosphate) and oxygen (O2) as cosubstrates, as well as the cofactors FAD (flavin adenine dinucleotide), FMN (flavin mononucleotide), tetrahydrobiopterin and heme. Interestingly, ascorbic acid appears to enhance NOS activity by increasing intracellular tetrahydrobiopterin. eNOS and nNOS synthesize NO in response to an increased concentration of calcium ions or in some cases in response to calcium-independent stimuli, such as shear stress. In vitro studies of NOS indicate that the Km of the enzyme for L-arginine is in the micromolar range. The concentration of L-arginine in endothelial cells, as well as in other cells, and in plasma is in the millimolar range. What this means is that, under physiological conditions, NOS is saturated with its L-arginine substrate. In other words, L-arginine would not be expected to be rate-limiting for the enzyme, and it would not appear that supraphysiological levels of L-arginine which could occur with oral supplementation of the amino acid would make any difference with regard to NO production. The reaction would appear to have reached its maximum level. However, in vivo studies have demonstrated that, under certain conditions, e.g. hypercholesterolemia, L-arginine could enhance endothelial-dependent vasodilation and NO production.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Health Effects
Health EffectRelationshipDirectionDescriptionReference
type 2 diabetes mellitusAssociated With?decreaseNot AvailablePMC5980341
psoriasisAssociated With?Not AvailableA disorder characterized by a quicker life span of skin cells causing cells to build up rapidly on the surface of the skin.PMC9866771
colitisHas Therapeutic Effect OnNot AvailableA disorder characterized by inflammation of the colon. (NCI CTCAE)PMC10981261
mucositisDecreased in Blood IndecreaseNot AvailablePMC9654368
DNA DamageHas Therapeutic Effect OnNot AvailableNot AvailablePMC13392519
Cellular SenescenceHas Therapeutic Effect OnNot AvailableNot AvailablePMC13392519
Intestinal inflammationIs Biomarker OfNot AvailableNot AvailablePMC12249471
Exposure Sources
Source IDSourceSectorReference
CEDs000010Insecticides?Insecticides are synthetic chemicals designed to control or eliminate insect pests that threaten crops and other agricultural products.Agriculture & land managementPubChem
CEDs000013Soil?Soil serves as a critical medium for plant growth and sustains various ecological functions; however, it can become a reservoir for synthetic chemical contamination.Agriculture & land managementPMC12742202
CEDs000233Brushes?Brushes used in personal care and cosmetics can be a source of synthetic chemical contamination due to the materials and coatings used in their manufacturing.Personal care & cosmeticsPubChem
CEDs000500Stairs And Ramps?Stairs and ramps in construction are often treated with various synthetic chemicals to enhance durability, slip resistance, and weather resistance.Building & ConstructionPubChem
CEDs000506Antennas?Antennas, commonly used in communication technologies, can be a source of synthetic chemical contamination through the materials and coatings used in their construction.Electrical & Electronic EquipmentPubChem
CEDs000508Coils?Coils are components used in various electrical and electronic applications, such as transformers, inductors, and motors.Electrical & Electronic EquipmentPubChem
CEDs000511Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.Electrical & Electronic EquipmentPubChem
CEDs000518Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.Electrical & Electronic EquipmentPubChem
CEDs000519Electrodes?Electrodes, used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials from which they are constructed and the processes involved in their manufacturing.Electrical & Electronic EquipmentPubChem
CEDs000521Fixed Capacitors And Their Manufacture?Fixed capacitors are passive electronic components used to store and release electrical energy, playing a critical role in various circuits.Electrical & Electronic EquipmentPubChem
CEDs000524Hybrid Capacitors?Hybrid capacitors are energy storage devices that combine the properties of electrolytic and supercapacitors, utilizing a combination of electrochemical principles to achieve higher energy density and power density.Electrical & Electronic EquipmentPubChem
CEDs000530Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.Electrical & Electronic EquipmentPubChem
CEDs000537Television Systems?Television systems can be a source of synthetic chemical contamination due to the various materials and components used in their manufacture and operation.Electrical & Electronic EquipmentPubChem
CEDs000539Video Games?Video games, through their production and disposal processes, can be a source of synthetic chemical contamination.Electrical & Electronic EquipmentPubChem
CEDs000544Fermentation Processes For Beer?Fermentation processes for beer involve the conversion of sugars into alcohol and carbon dioxide by yeast.Food, food processing & cookwarePubChem
CEDs000545Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.Food, food processing & cookwarePubChem
CEDs000547Preparation Of Malt?Malt preparation involves the germination and drying of cereal grains, primarily barley, to produce malt for brewing and food products.Food, food processing & cookwarePubChem
CEDs000548Preparation Of Vinegar?Vinegar is produced through the fermentation of ethanol by acetic acid bacteria, resulting in a solution that typically contains 4-8% acetic acid.Food, food processing & cookwarePubChem
CEDs000549Preparation Of Wine Or Sparkling Wine?The preparation of wine or sparkling wine involves various stages, including fermentation, aging, and bottling, which can introduce potential sources of synthetic chemical contamination.Food, food processing & cookwarePubChem
CEDs000550Preparation Of Wort?The preparation of wort involves the extraction of sugars from malted grains, a crucial step in the brewing process.Food, food processing & cookwarePubChem
CEDs000556Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.Household cleaning & consumer productsPubChem
CEDs000561Perfumes Within Detergents And Soaps?Perfumes within detergents and soaps are synthetic fragrance compounds added to enhance the sensory experience of cleaning products.Household cleaning & consumer productsPubChem
CEDs000563Soap Detergents?Soap detergents are synthetic surfactants designed to enhance the cleaning efficacy of water by reducing surface tension, allowing for better interaction with dirt and grease.Household cleaning & consumer productsPubChem
CEDs000567Tobacco Product Cases?Tobacco product cases can serve as a source of synthetic chemical contamination due to the presence of various additives and chemicals used in tobacco processing and product manufacturing.Household cleaning & consumer productsPubChem
CEDs000569Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.Household cleaning & consumer productsPubChem
CEDs000578Making Cigars?The process of making cigars involves several steps, including the cultivation of tobacco, fermentation, and the application of various additives to enhance flavor and preservation.Industrial manufacturing & chemical processingPubChem
CEDs000580Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.Industrial manufacturing & chemical processingPubChem
CEDs000581Paper Making Machines?Paper making machines utilize various synthetic chemicals throughout the production process, including additives, coatings, and bleaching agents.Industrial manufacturing & chemical processingPubChem
CEDs000592Marine Propulsion Or Steering?Marine propulsion and steering systems often rely on various synthetic chemicals, including lubricants, fuels, and hydraulic fluids.Marine, shipping & aquaculturePubChem
CEDs000596Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.Agriculture & land managementPubChem
CEDs000600Herbicides And Algicides?Herbicides and algicides are synthetic chemicals primarily used to control unwanted plants and algae in various environments.Agriculture & land managementPubChem
CEDs000602Molluscicides?Molluscicides are synthetic chemicals specifically designed to control and eliminate mollusks, such as snails and slugs, which can be detrimental to crops and agricultural productivity.Agriculture & land managementPubChem
CEDs000603Nematocides?Nematocides are synthetic chemicals specifically designed to control nematodes, which are microscopic roundworms that can cause significant damage to crops and plants.Agriculture & land managementPubChem
CEDs000604Pest Attractants?Pest attractants are synthetic chemicals designed to lure specific pests for monitoring or control purposes.Agriculture & land managementPubChem
CEDs000605Pest Repellants?Pest repellents, often formulated from synthetic chemicals, are widely used to protect crops from insect infestations and other pests.Agriculture & land managementPubChem
CEDs000606Plant Growth Regulators?Plant Growth Regulators (PGRs) are synthetic chemicals designed to influence the growth and development of plants.Agriculture & land managementPubChem
CEDs000607Rodenticides(1)?Rodenticides are synthetic chemicals specifically formulated to control rodent populations, serving as a crucial tool in managing pests that can damage crops and spread diseases.Agriculture & land managementPubChem
CEDs000608Rodenticides?Rodenticides are chemical substances specifically designed to control rodent populations by causing death through various mechanisms, including anticoagulation or neurotoxicity.Agriculture & land managementPubChem
CEDs000609Aftershave?Aftershave is a grooming product typically used to soothe and protect the skin following shaving.Personal care & cosmeticsPubChem
CEDs000610Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.Personal care & cosmeticsPubChem
CEDs000611Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.Personal care & cosmeticsPubChem
CEDs000612Body Washing Or Cleaning Implements?Body washing or cleaning implements, such as synthetic sponges, loofahs, and washcloths, can be sources of synthetic chemical contamination due to the materials used in their production.Personal care & cosmeticsPubChem
CEDs000613Depilatories?Depilatories are products designed to remove unwanted hair through the application of synthetic chemicals that break down the protein structure of hair, facilitating its removal.Personal care & cosmeticsPubChem
CEDs000614Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.Personal care & cosmeticsPubChem
CEDs000615Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.Personal care & cosmeticsPubChem
CEDs000617Lip Care Products?Lip care products, including lipsticks, balms, and glosses, often contain a variety of synthetic chemicals such as parabens, phthalates, and synthetic fragrances.Personal care & cosmeticsPubChem
CEDs000618Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.Personal care & cosmeticsPubChem
CEDs000620Card Games?Card games often utilize synthetic materials for playing cards and associated gaming equipment, which may contain various chemicals such as polyvinyl chloride (PVC), plastics, and dyes.Recreation & sports surfacesPubChem
CEDs000631Anthraquinone Dyes?Anthraquinone dyes are a class of synthetic organic compounds characterized by their vibrant colors and stability, making them widely used in various applications, particularly in coloring textiles and leather.Textiles, leather & furnishingsPubChem
CEDs000632Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.Textiles, leather & furnishingsPubChem
CEDs000642Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.Textiles, leather & furnishingsPubChem
CEDs000662Yarns Or Threads?Yarns or threads used in textiles can be a source of synthetic chemical contamination due to the production processes and treatments they undergo.Textiles, leather & furnishingsPubChem
CEDs000671Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.Aviation & AerospacePubChem
CEDs000673Unmanned Aerial Vehicles?Unmanned Aerial Vehicles (UAVs), commonly known as drones, utilize various synthetic chemicals in their manufacturing, operation, and maintenance processes.Aviation & AerospacePubChem
CEDs000678Nitrogenous Fertilisers?Nitrogenous fertilizers are synthetic chemical compounds primarily used to enhance plant growth by supplying essential nitrogen, a crucial nutrient for photosynthesis and protein synthesis.Agriculture & land managementPubChem
CEDs000679Phosphatic Fertilisers?Phosphatic fertilizers are synthetic chemical products primarily composed of phosphorus, which is essential for plant growth.Agriculture & land managementPubChem
CEDs000685Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.Building & ConstructionPubChem
CEDs000688Glass Coatings?Glass coatings are synthetic chemical formulations applied to glass surfaces to enhance properties such as durability, UV resistance, and aesthetic appeal.Building & ConstructionPubChem
CEDs000693Silica Glass?Silica glass, primarily composed of silicon dioxide (SiO2), is widely used in various applications, including windows, glass facades, and insulation materials.Building & ConstructionPubChem
CEDs000696Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.Industrial manufacturing & chemical processingPubChem
CEDs000698Jewellery?Jewellery production often involves the use of various synthetic chemicals during the extraction and processing of metals.Mining & metal processingPubChem
CEDs000727Printing Machines Or Presses?Printing machines or presses commonly utilize synthetic chemicals such as inks, solvents, and cleaning agents.Paper, pulp & fiber productsPubChem
CEDs000734Coating Compositions?Coating compositions, which include paints, sealants, and varnishes, are formulated with a variety of synthetic chemicals such as solvents, resins, pigments, and additives.Building & ConstructionPubChem
CEDs000739Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.Paper, pulp & fiber productsPubChem
CEDs000740Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.Paper, pulp & fiber productsPubChem
CEDs000743Sludge Treatment?Sludge treatment involves the processing of waste materials generated from wastewater treatment plants, which often contain a variety of organic and inorganic substances.Wastewater, sanitation & biosolidsPubChem
CEDs000744Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.Wastewater, sanitation & biosolidsPubChem
CEDs01302WineFood, food processing & cookwarePMC4609976
CEDs01429Soy SauceFood, food processing & cookwarePMC4609976
CEDs02255WaterAquatic systems & sedimentsPMC5553857
Pathways
136 pathwaysPathway Source: PathBank
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Nitric oxide synthase, inducible structureClick to view 3D structureNitric oxide synthase, inducibleP35228HumansKnownNot Available
Nitric oxide synthase 3 structureClick to view 3D structureNitric oxide synthase 3P29474HumansKnownNot Available
Argininosuccinate synthase structureClick to view 3D structureArgininosuccinate synthaseP00966HumansKnownNot Available
Ornithine transcarbamylase, mitochondrial structureClick to view 3D structureOrnithine transcarbamylase, mitochondrialP00480HumansPredicted (SEA)
Prediction Confidence Score
0.588
Applicability Domain
0.588
Statistical Significance
1.00e-05
Supporting Reference Compounds
1
E-value
0.0778492
Nitric oxide synthase, inducible structureClick to view 3D structureNitric oxide synthase, inducibleP35228HumansPredicted (SEA)
Prediction Confidence Score
0.55
Applicability Domain
0.724
Statistical Significance
4.00e-05
Supporting Reference Compounds
47
E-value
0.311397
Arginase structureClick to view 3D structureArginaseQ8I384Plasmodium falciparumPredicted (SEA)
Prediction Confidence Score
0.469
Applicability Domain
0.469
Statistical Significance
6.00e-05
Supporting Reference Compounds
1
E-value
0.467095
Arginase-2, mitochondrial structureClick to view 3D structureArginase-2, mitochondrialP78540HumansPredicted (SEA)
Prediction Confidence Score
0.462
Applicability Domain
0.625
Statistical Significance
4.00e-05
Supporting Reference Compounds
7
E-value
0.311397
Nitric oxide synthase, inducible structureClick to view 3D structureNitric oxide synthase, inducibleP29477Mus musculusPredicted (SEA)
Prediction Confidence Score
0.444
Applicability Domain
0.645
Statistical Significance
3.00e-04
Supporting Reference Compounds
47
E-value
2.33548
Click to view 3D structureMetabotropic glutamate receptor 8P47743Mus musculusPredicted (SEA)
Prediction Confidence Score
0.427
Applicability Domain
0.448
Statistical Significance
6.00e-05
Supporting Reference Compounds
2
E-value
0.467095
Nitric oxide synthase 1 structureClick to view 3D structureNitric oxide synthase 1P29475HumansPredicted (SEA)
Prediction Confidence Score
0.426
Applicability Domain
0.645
Statistical Significance
5.90e-04
Supporting Reference Compounds
65
E-value
4.5931
Nitric oxide synthase 1 structureClick to view 3D structureNitric oxide synthase 1P29476Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.41
Applicability Domain
0.645
Statistical Significance
5.50e-04
Supporting Reference Compounds
49
E-value
4.28171
Arginase-1 structureClick to view 3D structureArginase-1P05089HumansPredicted (SEA)
Prediction Confidence Score
0.405
Applicability Domain
0.625
Statistical Significance
5.00e-05
Supporting Reference Compounds
8
E-value
0.389246
Click to view 3D structureMetabotropic glutamate receptor 6P35349Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.4
Applicability Domain
0.448
Statistical Significance
1.40e-04
Supporting Reference Compounds
24
E-value
1.08989
Click to view 3D structureAsc-type amino acid transporter 1P63116RatPredicted (SEA)
Prediction Confidence Score
0.393
Applicability Domain
0.393
Statistical Significance
1.00e-04
Supporting Reference Compounds
2
E-value
0.778492
Click to view 3D structureMetabotropic glutamate receptor 2P31421Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.389
Applicability Domain
0.448
Statistical Significance
5.50e-04
Supporting Reference Compounds
53
E-value
4.28171
Click to view 3D structureMetabotropic glutamate receptor 4P31423Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.382
Applicability Domain
0.448
Statistical Significance
4.40e-04
Supporting Reference Compounds
38
E-value
3.42537
Betaine--homocysteine S-methyltransferase 1 structureClick to view 3D structureBetaine--homocysteine S-methyltransferase 1Q93088HumansPredicted (SEA)
Prediction Confidence Score
0.378
Applicability Domain
0.378
Statistical Significance
8.00e-05
Supporting Reference Compounds
1
E-value
0.622794
Arginase-1 structureClick to view 3D structureArginase-1P07824Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.378
Applicability Domain
0.625
Statistical Significance
3.00e-05
Supporting Reference Compounds
6
E-value
0.233548
Click to view 3D structureMetabotropic glutamate receptor 6O15303HumansPredicted (SEA)
Prediction Confidence Score
0.372
Applicability Domain
0.448
Statistical Significance
2.80e-04
Supporting Reference Compounds
39
E-value
2.17978
Glutamate receptor ionotropic, kainate 1 structureClick to view 3D structureGlutamate receptor ionotropic, kainate 1P22756Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.368
Applicability Domain
0.448
Statistical Significance
2.20e-04
Supporting Reference Compounds
45
E-value
1.71268
Metabotropic glutamate receptor 4 structureClick to view 3D structureMetabotropic glutamate receptor 4Q14833HumansPredicted (SEA)
Prediction Confidence Score
0.367
Applicability Domain
0.448
Statistical Significance
0.0013
Supporting Reference Compounds
69
E-value
10.1204
Click to view 3D structureMetabotropic glutamate receptor 8P70579Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.364
Applicability Domain
0.448
Statistical Significance
2.70e-04
Supporting Reference Compounds
28
E-value
2.10193
Excitatory amino acid transporter 3 structureClick to view 3D structureExcitatory amino acid transporter 3P43005HumansPredicted (SEA)
Prediction Confidence Score
0.36
Applicability Domain
0.448
Statistical Significance
3.00e-04
Supporting Reference Compounds
13
E-value
2.33548
Glutamate receptor ionotropic, kainate 3 structureClick to view 3D structureGlutamate receptor ionotropic, kainate 3P42264Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.355
Applicability Domain
0.448
Statistical Significance
2.70e-04
Supporting Reference Compounds
26
E-value
2.10193
Metabotropic glutamate receptor 8 structureClick to view 3D structureMetabotropic glutamate receptor 8O00222HumansPredicted (SEA)
Prediction Confidence Score
0.352
Applicability Domain
0.448
Statistical Significance
3.60e-04
Supporting Reference Compounds
48
E-value
2.80257
Glutamate receptor ionotropic, kainate 2 structureClick to view 3D structureGlutamate receptor ionotropic, kainate 2P42260Rattus norvegicusPredicted (SEA)
Prediction Confidence Score
0.352
Applicability Domain
0.448
Statistical Significance
1.90e-04
Supporting Reference Compounds
18
E-value
1.47914
Glutamine synthetase structureClick to view 3D structureGlutamine synthetaseP0A9C5Escherichia coli K-12Predicted (SEA)
Prediction Confidence Score
0.351
Applicability Domain
0.351
Statistical Significance
1.50e-04
Supporting Reference Compounds
1
E-value
1.16774
Click to view 3D structureS-methylmethionine--homocysteine S-methyltransferase BHMT2Q9H2M3HumansPredicted (SEA)
Prediction Confidence Score
0.351
Applicability Domain
0.351
Statistical Significance
1.50e-04
Supporting Reference Compounds
1
E-value
1.16774
Argininosuccinate synthase structureClick to view 3D structureArgininosuccinate synthaseP00966HumansKnownNot Available
Click to view 3D structureargininosuccinate synthaseQ5T6L4HumansKnownNot Available
Nitric oxide synthase 1 structureClick to view 3D structureNitric oxide synthase 1P29475HumansKnownNot Available
Nitric oxide synthase 3 structureClick to view 3D structureNitric oxide synthase 3P29474HumansKnownNot Available
Nitric oxide synthase, inducible structureClick to view 3D structureNitric oxide synthase, inducibleP35228HumansKnownNot Available
Protein-arginine deiminase type-4 structureClick to view 3D structureProtein-arginine deiminase type-4Q9UM07HumansKnownNot Available
N(G),N(G)-dimethylarginine dimethylaminohydrolase 1 structureClick to view 3D structureN(G),N(G)-dimethylarginine dimethylaminohydrolase 1O94760HumansKnownNot Available
Protein-arginine deiminase type-3 structureClick to view 3D structureProtein-arginine deiminase type-3Q9ULW8HumansKnownNot Available
Click to view 3D structurePutative hydrolase DDAH2O95865HumansKnownNot Available
Ornithine transcarbamylase, mitochondrial structureClick to view 3D structureOrnithine transcarbamylase, mitochondrialP00480HumansKnownNot Available
Inactive protein-arginine deiminase type-6 structureClick to view 3D structureInactive protein-arginine deiminase type-6Q6TGC4HumansKnownNot Available
Protein-arginine deiminase type-1 structureClick to view 3D structureProtein-arginine deiminase type-1Q9ULC6HumansKnownNot Available
Protein-arginine deiminase type-2 structureClick to view 3D structureProtein-arginine deiminase type-2Q9Y2J8HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00155
HMDB IDHMDB0000904
FooDB IDFDB011841
Phenol Explorer IDNot Available
KNApSAcK IDC00001348
BiGG ID34627
BioCyc IDL-CITRULLINE
METLIN ID16
PDB IDNot Available
Wikipedia LinkCitrulline
Chemspider ID9367
ChEBI ID16349
PubChem Compound ID9750
Kegg Compound IDC00327
YMDB IDYMDB00060
ECMDB IDECMDB00904
References
Synthesis Reference

Hua Bai, Peijie Yang, Zhengjie Chen, Chongyan Xu, Zhaorul Li, Zigang Zhao, Luyan Jiang, Zongyi Yang, Jiang Li, “PROCESSES FOR THE PRODUCTION OF L-CITRULLINE.” U.S. Patent US20090142813, issued June 04, 2009.

MSDSLink
General References
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  6. Crenn P, Coudray-Lucas C, Thuillier F, Cynober L, Messing B: Postabsorptive plasma citrulline concentration is a marker of absorptive enterocyte mass and intestinal failure in humans. Gastroenterology. 2000 Dec;119(6):1496-505. [PubMed: 11113071]
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  8. Jianfeng G, Weiming Z, Ning L, Fangnan L, Li T, Nan L, Jieshou L: Serum citrulline is a simple quantitative marker for small intestinal enterocytes mass and absorption function in short bowel patients. J Surg Res. 2005 Aug;127(2):177-82. [PubMed: 15921697]
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  11. Potter MA, Zeesman S, Brennan B, Kobayashi K, Gao HZ, Tabata A, Saheki T, Whelan DT: Pregnancy in a healthy woman with untreated citrullinemia. Am J Med Genet A. 2004 Aug 15;129A(1):77-82. [PubMed: 15266621]
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  13. Melis GC, Boelens PG, van der Sijp JR, Popovici T, De Bandt JP, Cynober L, van Leeuwen PA: The feeding route (enteral or parenteral) affects the plasma response of the dipetide Ala-Gln and the amino acids glutamine, citrulline and arginine, with the administration of Ala-Gln in preoperative patients. Br J Nutr. 2005 Jul;94(1):19-26. [PubMed: 16115328]
  14. Reparon-Schuijt CC, van Esch WJ, van Kooten C, Schellekens GA, de Jong BA, van Venrooij WJ, Breedveld FC, Verweij CL: Secretion of anti-citrulline-containing peptide antibody by B lymphocytes in rheumatoid arthritis. Arthritis Rheum. 2001 Jan;44(1):41-7. [PubMed: 11212174]
  15. Maruyama H, Ogawa M, Nishio T, Kobayashi K, Saheki T, Sunohara N: Citrullinemia type II in a 64-year-old man with fluctuating serum citrulline levels. J Neurol Sci. 2001 Jan 1;182(2):167-70. [PubMed: 11137523]
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