Gramicidin S (CED0002955)

Record Information
Version1.0
Creation Date2016-05-22 05:27:33 UTC
Update Date2026-08-23 03:11:13 UTC
Accession NumberCHEM018690
Identification
Common NameGramicidin S
ClassSmall Molecule
Description
Gramicidin S is a compound with the chemical formula C60H92N12O10. Gramicidin S belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. With an average molecular weight of 1,141 g/mol, Gramicidin S is a heavy molecule. It is found in or released from healthcare, pharmaceuticals, and veterinary products as an antibiotic. Recorded exposure routes for this compound include inhalation and oral administration.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
Cyclo(L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl)ChEBI
GramicidinChEBI
Gramicidin CChEBI
Gramicin S 1ChEBI
Gramicin S-aChEBI
Linear gramicidinMeSH
Gramicidin DMeSH
GramodermMeSH
Gramicidin bMeSH
Gramicidin dubosMeSH
GramicidinsMeSH
Gramicidin NFMeSH
Gramicidin, linearMeSH
Gramicidin aMeSH
Gramicidin a(1)MeSH
Gramicidin KMeSH
Gramicidin JMeSH
Gramicidin pMeSH
Chemical FormulaC60H92N12O10
Average Molecular Mass1141.470 g/mol
Monoisotopic Mass1140.706 g/mol
CAS Registry Number113-73-5
IUPAC Name(3R,6S,9S,12S,15S,21R,24S,27S,30S,33S)-9,27-bis(3-aminopropyl)-3,21-dibenzyl-5,8,11,14,23,26,29,32-octahydroxy-6,24-bis(2-methylpropyl)-12,30-bis(propan-2-yl)-1,4,7,10,13,19,22,25,28,31-decaazatricyclo[31.3.0.0¹⁵,¹⁹]hexatriaconta-4,7,10,13,22,25,28,31-octaene-2,20-dione
Traditional Namegramicidina S
SMILES[H][C@@]12CCCN1C(=O)[C@@]([H])(CC1=CC=CC=C1)N=C(O)[C@]([H])(CC(C)C)N=C(O)[C@]([H])(CCCN)N=C(O)[C@@]([H])(N=C(O)[C@]1([H])CCCN1C(=O)[C@@]([H])(CC1=CC=CC=C1)N=C(O)[C@]([H])(CC(C)C)N=C(O)[C@]([H])(CCCN)N=C(O)[C@@]([H])(N=C2O)C(C)C)C(C)C
InChI IdentifierInChI=1S/C60H92N12O10/c1-35(2)31-43-53(75)67-45(33-39-19-11-9-12-20-39)59(81)71-29-17-25-47(71)55(77)70-50(38(7)8)58(80)64-42(24-16-28-62)52(74)66-44(32-36(3)4)54(76)68-46(34-40-21-13-10-14-22-40)60(82)72-30-18-26-48(72)56(78)69-49(37(5)6)57(79)63-41(23-15-27-61)51(73)65-43/h9-14,19-22,35-38,41-50H,15-18,23-34,61-62H2,1-8H3,(H,63,79)(H,64,80)(H,65,73)(H,66,74)(H,67,75)(H,68,76)(H,69,78)(H,70,77)/t41-,42-,43-,44-,45+,46+,47-,48-,49-,50-/m0/s1
InChI KeyIUAYMJGZBVDSGL-XNNAEKOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic peptides. Cyclic peptides are compounds containing a cyclic moiety bearing a peptide backbone.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCyclic peptides
Alternative Parents
Substituents
  • Cyclic alpha peptide
  • Alpha-amino acid or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Cyclic carboximidic acid
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Polyol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Carbonyl group
  • Organic oxygen compound
  • Primary amine
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP2.57ALOGPS
logP8.18ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.08ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area353.38 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity312.52 m³·mol⁻¹ChemAxon
Polarizability122.65 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dl-0900000000-9bd08d6ccc468dc6fe7dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05fu-2900010000-341f51d469fd873cee82Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-6915387666-0ab7e3699e8b3406fc46Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000j-6901120000-ef8a254f6dcec51731ecNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dj-9400000000-f6c68ddd81f55d57b7c3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-000l-3541795454-22160ca28798d4c9b50bNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity ValuesNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Nicotinamide N-methyltransferase structureClick to view 3D structureNicotinamide N-methyltransferaseO55239Mus musculusPredicted (SEA)9.9647
T-cell surface antigen CD2 structureClick to view 3D structureT-cell surface antigen CD2P06729HumansPredicted (SEA)18.7617
Click to view 3D structureMelanocortin receptor 4P56450Mus musculusPredicted (SEA)144.021
Kelch-like protein 20 structureClick to view 3D structureKelch-like protein 20Q9Y2M5HumansPredicted (SEA)7.23998
Click to view 3D structureAureobasidin-resistance proteinQ9Y745Neosartorya fumigata (Aspergillus fumigatus)Predicted (SEA)6.61718
Plasma kallikrein structureClick to view 3D structurePlasma kallikreinP03952HumansPredicted (SEA)149.315
Inducible T-cell costimulator structureClick to view 3D structureInducible T-cell costimulatorQ9Y6W8HumansPredicted (SEA)32.6967
Actin, cytoplasmic 1 structureClick to view 3D structureActin, cytoplasmic 1O93400Xenopus laevisPredicted (SEA)10.6653
Click to view 3D structureMelanocortin receptor 3P33033Mus musculusPredicted (SEA)159.98
Endothelin-1 receptor structureClick to view 3D structureEndothelin-1 receptorP25101HumansPredicted (SEA)117.474
Calcium and integrin-binding protein 1 structureClick to view 3D structureCalcium and integrin-binding protein 1Q99828HumansPredicted (SEA)45.6975
Plasma kallikrein structureClick to view 3D structurePlasma kallikreinP26262Mus musculusPredicted (SEA)43.4399
Kallikrein-7 structureClick to view 3D structureKallikrein-7P49862HumansPredicted (SEA)41.4936
Cathepsin G structureClick to view 3D structureCathepsin GP08311HumansPredicted (SEA)66.8725
Serine protease 1 structureClick to view 3D structureSerine protease 1P00760Bos taurusPredicted (SEA)145.889
Plasminogen structureClick to view 3D structurePlasminogenP00747HumansPredicted (SEA)283.138
Click to view 3D structureEndothelin-1 receptorQ29010Sus scrofaPredicted (SEA)58.3869
Prothrombin structureClick to view 3D structureProthrombinP00734HumansPredicted (SEA)408.086
Melanocortin receptor 4 structureClick to view 3D structureMelanocortin receptor 4P32245HumansPredicted (SEA)233.392
Click to view 3D structureMu-type opioid receptorP33535Rattus norvegicusPredicted (SEA)408.942
Epidermal growth factor receptor substrate 15 structureClick to view 3D structureEpidermal growth factor receptor substrate 15P42566HumansPredicted (SEA)49.045
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)823.645
Click to view 3D structureCCN family member 2P29279HumansPredicted (SEA)49.8235
Kallikrein-4 structureClick to view 3D structureKallikrein-4Q9Y5K2HumansPredicted (SEA)72.9447
Suppressor of tumorigenicity 14 protein structureClick to view 3D structureSuppressor of tumorigenicity 14 proteinQ9Y5Y6HumansPredicted (SEA)205.755
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGramicidin S
Chemspider IDNot Available
ChEBI ID5530
PubChem Compound ID73357
Kegg Compound IDC11218
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References