Guanine (CED0000718)

Record Information
Version1.0
Creation Date2016-05-25 18:08:09 UTC
Update Date2026-05-14 17:35:43 UTC
Accession NumberCHEM021610
Identification
Common NameGuanine
ClassSmall Molecule
Description
Guanine is an organic compound with the chemical formula C5H5N5O and an average molecular weight of 151.13 g/mol. Guanine belongs to the purines and purine derivatives, a subclass of imidazopyrimidines within the organic compounds. Industrially, the compound is utilized as a dye and an opacifer. Regarding environmental presence and exposure, guanine is recorded as being found in indoor air, dust, and atmospheric transport, with inhalation listed as a recorded exposure route. In biological systems, the compound interacts with several protein targets. It acts as an inhibitor of purine nucleoside phosphorylase (PNP), purine nucleoside phosphorylase 2 (xapA), xanthine-guanine phosphoribosyltransferase (gpt), and GTP cyclohydrolase 1 (GCH1), in addition to one other protein.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-6-hydroxypurineChEBI
2-Amino-6-oxopurineChEBI
GChEBI
GuaChEBI
2-Amino-1,7-dihydro-6H-purin-6-oneHMDB
2-Amino-1,9-dihydro-6H-purin-6-oneHMDB
2-Amino-1,9-dihydro-purin-6-oneHMDB
2-Amino-3,7-dihydro-6H-purin-6-oneHMDB
2-Amino-6-hydroxy-1H-purineHMDB
2-Amino-6-purinolHMDB
2-Amino-hypoxanthineHMDB
2-AminohypoxanthineHMDB
6-Hydroxy-2-aminopurineHMDB
C.I. natural white 1HMDB
CI natural white 1HMDB
Dew pearlHMDB
GuaninHMDB
Guanine enolHMDB
GUNHMDB
MearlmaidHMDB
Mearlmaid aaHMDB
Natural pearl essenceHMDB
Natural white 1HMDB
NaturonHMDB
PathocidinHMDB
Pearl essenceHMDB
Stella polarisHMDB
Chemical FormulaC5H5N5O
Average Molecular Mass151.126 g/mol
Monoisotopic Mass151.049 g/mol
CAS Registry Number73-40-5
IUPAC Name2-amino-6,7-dihydro-3H-purin-6-one
Traditional Name2-aminohypoxanthine
SMILESNC1=NC(=O)C2=C(N1)N=CN2
InChI IdentifierInChI=1S/C5H5N5O/c6-5-9-3-2(4(11)10-5)7-1-8-3/h1H,(H4,6,7,8,9,10,11)
InChI KeyUYTPUPDQBNUYGX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as purines and purine derivatives. These are aromatic heterocyclic compounds containing a purine moiety, which is formed a pyrimidine-ring ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct ParentPurines and purine derivatives
Alternative Parents
Substituents
  • Purine
  • Hydroxypyrimidine
  • Pyrimidine
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • 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 Solubility2.31 g/LALOGPS
logP-0.92ALOGPS
logP-0.59ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)8.95ChemAxon
pKa (Strongest Basic)2.22ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.16 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.9 m³·mol⁻¹ChemAxon
Polarizability13.34 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0udi-1938000000-e15e09f2007f35659bb9Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0udi-3739000000-66a080b08ba9b9f82e20Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0udi-5900000000-0a63148e3a8dc8d026dfNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0udi-1938000000-e15e09f2007f35659bb9Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0udi-3739000000-66a080b08ba9b9f82e20Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0udi-2928000000-073bf70794fe99ce737fNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-000t-2790000000-77e6b5b71c9ff6ad2b23Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0ff0-5900000000-f103c75addeafe7ac6f0Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0901000000-2864e73c83444d566e9aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2900000000-4229d3d01623054b4cebNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-d5ae84fefadd84f988b4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-7d48b2e8db6967e98407Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0uxr-0900000000-67a7784963ec75cecaa0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00di-9000000000-4569516f23d8a712b434Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-d928cac1226f19b8edc3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-34059351f2cbd94a8accNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udj-0903100000-deb9c022884d7c98782eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-45d9db80ce4657ef1773Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-1900000000-86b7ee5755cbb8236f5bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-ba534850b64f39d81fa0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-422f992621ab9626d1b2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f89-0900000000-64e388178db73f06cb20Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-f0a95c55947ca990359cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-45d9db80ce4657ef1773Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-ba534850b64f39d81fa0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f89-0900000000-64e388178db73f06cb20Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-c2e1c1e8841cc741dac1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-0840e50df6a1013fdd24Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0a4i-2900000000-4229d3d01623054b4cebNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000i-0900000000-d5ae84fefadd84f988b4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0900000000-d77cafe24ec50283bbf8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-34059351f2cbd94a8accNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-422f992621ab9626d1b2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f89-0900000000-074d4bf3ce668d5a6900Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-028ceecf0841171716cbNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-b05c7913e77f52057236Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f79-0900000000-90b22c34acfe066ec487Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-47aa8ed6cc7378cbc969Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-e74c005384d71f4787e5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-de4a4c4479ea93d742b5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a5i-9800000000-da506476184e5c2313a4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-03d17084c3cb072c0237Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-2900000000-c372e3ba919cba4f561fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-9200000000-8ac435f998deda6437e1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-361a2474138028086bb3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-3f721c7615699e9896e6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zgi-9600000000-40c274213b562f2c5303Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-21c3d82f91283a8a49e6Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udl-3900000000-368985d5f972ab750ed2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-9000000000-06d2f3b2019589a69a3bNot AvailableView Spectrum
MSMS Spectrumsplash10-0udi-8900000000-699c510cfaf838ab1922Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, H2O, experimental)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1138.0Log mg/kg[640:2000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
19Indoor airAir, dust & atmospheric transportNot Available
490Personal care & cosmeticsNot Available
Pathways
40 pathways
Purine Metabolism
Purine Metabolism
Adenosine Deaminase Deficiency
Adenosine Deaminase Deficiency
Adenylosuccinate Lyase Deficiency
Adenylosuccinate Lyase Deficiency
Gout or Kelley-Seegmiller Syndrome
Gout or Kelley-Seegmiller Syndrome
Lesch-Nyhan Syndrome (LNS)
Lesch-Nyhan Syndrome (LNS)
Molybdenum Cofactor Deficiency
Molybdenum Cofactor Deficiency
Xanthine Dehydrogenase Deficiency (Xanthinuria)
Xanthine Dehydrogenase Deficiency (Xanthinuria)
Purine Nucleoside Phosphorylase Deficiency
Purine Nucleoside Phosphorylase Deficiency
AICA-Ribosiduria
AICA-Ribosiduria
Azathioprine Action Pathway
Azathioprine Action Pathway
Mercaptopurine Action Pathway
Mercaptopurine Action Pathway
Thioguanine Action Pathway (old)
Thioguanine Action Pathway (old)
View all 40 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureXanthine dehydrogenaseO54050Rhodobacter capsulatusPredicted (SEA)0.467095
Queuine tRNA-ribosyltransferase catalytic subunit 1 structureClick to view 3D structureQueuine tRNA-ribosyltransferase catalytic subunit 1Q9BXR0HumansPredicted (SEA)4.20386
Gastrotropin structureClick to view 3D structureGastrotropinP51161HumansPredicted (SEA)2.10193
Purine nucleoside phosphorylase structureClick to view 3D structurePurine nucleoside phosphorylaseP00491HumansPredicted (SEA)8.25202
Adenosine receptor A2b structureClick to view 3D structureAdenosine receptor A2bP29275HumansPredicted (SEA)658.527
Click to view 3D structureAdenosine receptor A1P25099Rattus norvegicusPredicted (SEA)576.006
Click to view 3D structurePurine nucleoside phosphorylaseP55859Bos taurusPredicted (SEA)2.80257
Guanine deaminase structureClick to view 3D structureGuanine deaminaseQ9Y2T3HumansPredicted (SEA)0.389246
Dual specificity tyrosine-phosphorylation-regulated kinase 1A structureClick to view 3D structureDual specificity tyrosine-phosphorylation-regulated kinase 1AQ13627HumansPredicted (SEA)3552.65
Click to view 3D structureAdenosine receptor A1P47745Cavia porcellusPredicted (SEA)80.4961
Click to view 3D structure2-amino-4-hydroxy-6-hydroxymethyldihydropteridin e pyrophosphokinaseX5EH84Staphylococcus aureusPredicted (SEA)6.38364
Click to view 3D structureSerine/threonine protein kinase UL97P16788HHV-5Predicted (SEA)5.52729
Dihydrofolate synthase/folylpolyglutamate synthase structureClick to view 3D structureDihydrofolate synthase/folylpolyglutamate synthaseP08192Escherichia coli (strain K12)Predicted (SEA)20.5522
Leucine-rich repeat serine/threonine-protein kinase 2 structureClick to view 3D structureLeucine-rich repeat serine/threonine-protein kinase 2Q5S007HumansPredicted (SEA)2920.82
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)1851.96
2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinase structureClick to view 3D structure2-amino-4-hydroxy-6-hydroxymethyldihydropteridine pyrophosphokinaseP26281Escherichia coli (strain K12)Predicted (SEA)4.7488
Thymidylate synthase structureClick to view 3D structureThymidylate synthaseP04818HumansPredicted (SEA)138.572
Click to view 3D structureAdenosine receptor A2aP30543Rattus norvegicusPredicted (SEA)981.445
Click to view 3D structureAdenosine receptor A2aP46616Cavia porcellusPredicted (SEA)100.114
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)2323.25
Cyclin-dependent kinase 2 structureClick to view 3D structureCyclin-dependent kinase 2P24941HumansPredicted (SEA)4923.5
Purine nucleoside phosphorylase structureClick to view 3D structurePurine nucleoside phosphorylaseQ8I3X4Plasmodium falciparum (isolate 3D7)Predicted (SEA)1.63483
Click to view 3D structureAdenosine receptor A2bP29276Rattus norvegicusPredicted (SEA)190.264
Aurora kinase A structureClick to view 3D structureAurora kinase AO14965HumansPredicted (SEA)5027.27
Click to view 3D structureBifunctional dihydrofolate reductase-thymidylate synthaseQ07422Toxoplasma gondiiPredicted (SEA)380.371
Concentrations
Not Available
External Links
DrugBank IDDB02377
HMDB IDHMDB0000132
FooDB IDFDB004222
Phenol Explorer IDNot Available
KNApSAcK IDC00001501
BiGG ID34363
BioCyc IDGUANINE
METLIN ID315
PDB IDNot Available
Wikipedia LinkGuanine
Chemspider ID744
ChEBI ID16235
PubChem Compound ID764
Kegg Compound IDC00242
YMDB IDYMDB00698
ECMDB IDECMDB00132
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Xiao, Xuhua; Ma, Weiyong. One-pot synthesis of guanine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp.
2. Tiemeyer W, Stohrer M, Giesecke D: Metabolites of nucleic acids in bovine milk. J Dairy Sci. 1984 Apr;67(4):723-8. doi: 10.3168/jds.S0022-0302(84)81361-2.
3. Xiao, Xuhua; Ma, Weiyong. One-pot synthesis of guanine. Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 10pp.
4. Boulias C, Moscarello MA: Guanine nucleotides stimulate hydrolysis of phosphatidyl inositol bis phosphate in human myelin membranes. Biochem Biophys Res Commun. 1989 Jul 14;162(1):282-7.
5. Harkness RA: Hypoxanthine, xanthine and uridine in body fluids, indicators of ATP depletion. J Chromatogr. 1988 Jul 29;429:255-78.
6. Castro-Gago M, Cid E, Trabazo S, Pavon P, Camina F, Rodriguez-Segade S, Einis Punal J, Rodriguez-Nunez A: Cerebrospinal fluid purine metabolites and pyrimidine bases after brief febrile convulsions. Epilepsia. 1995 May;36(5):471-4.
7. Steyn LM, Harley EH: Intracellular activity of HPRT Cape Town: purine uptake and growth of cultured cells in selective media. J Inherit Metab Dis. 1985;8(4):198-203.
8. Yafe A, Etzioni S, Weisman-Shomer P, Fry M: Formation and properties of hairpin and tetraplex structures of guanine-rich regulatory sequences of muscle-specific genes. Nucleic Acids Res. 2005 May 20;33(9):2887-900. Print 2005.
9. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30.
10. Russo TA, Jodush ST, Brown JJ, Johnson JR: Identification of two previously unrecognized genes (guaA and argC) important for uropathogenesis. Mol Microbiol. 1996 Oct;22(2):217-29.
11. Liu Z, Li T, Wang E: Simultaneous determination of guanine, uric acid, hypoxanthine and xanthine in human plasma by reversed-phase high-performance liquid chromatography with amperometric detection. Analyst. 1995 Aug;120(8):2181-4.
12. Parkinson SJ, Waldman SA: An intracellular adenine nucleotide binding site inhibits guanyly cyclase C by a guanine nucleotide-dependent mechanism. Biochemistry. 1996 Mar 12;35(10):3213-21.
13. Rodriguez-Nunez A, Camina F, Lojo S, Rodriguez-Segade S, Castro-Gago M: Concentrations of nucleotides, nucleosides, purine bases and urate in cerebrospinal fluid of children with meningitis. Acta Paediatr. 1993 Oct;82(10):849-52.
14. Groopman JD, Zhu JQ, Donahue PR, Pikul A, Zhang LS, Chen JS, Wogan GN: Molecular dosimetry of urinary aflatoxin-DNA adducts in people living in Guangxi Autonomous Region, People's Republic of China. Cancer Res. 1992 Jan 1;52(1):45-52.
15. Shioya M, Wakabayashi K, Yamashita K, Nagao M, Sugimura T: Formation of 8-hydroxydeoxyguanosine in DNA treated with fecapentaene-12 and -14. Mutat Res. 1989 Mar;225(3):91-4.
16. Allgayer H, Kolb M, Stuber V, Kruis W: Effects of bile acids on base hydroxylation in a model of human colonic mucosal DNA. Cancer Detect Prev. 2002;26(1):85-9.
17. Schei MA, Hessen JO, Lund E: House-dust mites and mattresses. Allergy. 2002 Jun;57(6):538-42.
18. Weimann A, Belling D, Poulsen HE: Quantification of 8-oxo-guanine and guanine as the nucleobase, nucleoside and deoxynucleoside forms in human urine by high-performance liquid chromatography-electrospray tandem mass spectrometry. Nucleic Acids Res. 2002 Jan 15;30(2):E7.
19. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762.
20. Niles JC, Wishnok JS, Tannenbaum SR: Peroxynitrite-induced oxidation and nitration products of guanine and 8-oxoguanine: structures and mechanisms of product formation. Nitric Oxide. 2006 Mar;14(2):109-21. Epub 2005 Dec 13.
21. Spiegel AM: Signal transduction by guanine nucleotide binding proteins. Mol Cell Endocrinol. 1987 Jan;49(1):1-16.
22. Fain JN, Wallace MA, Wojcikiewicz RJ: Evidence for involvement of guanine nucleotide-binding regulatory proteins in the activation of phospholipases by hormones. FASEB J. 1988 Jul;2(10):2569-74.
23. Sculley DG, Dawson PA, Emmerson BT, Gordon RB: A review of the molecular basis of hypoxanthine-guanine phosphoribosyltransferase (HPRT) deficiency. Hum Genet. 1992 Nov;90(3):195-207.
24. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=22770225
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=8070089