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Human Metabolome Database Version 3.5

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Showing metabocard for Primapterin (HMDB02263)

Record Information
Version 3.5
Creation Date 2006-05-22 08:17:45 -0600
Update Date 2013-02-08 17:11:39 -0700
HMDB ID HMDB02263
Secondary Accession Numbers None
Metabolite Identification
Common Name Primapterin
Description Primapterin and anapterin are present in very low concentrations in every human urine, as well as in the liver of man. - PMID: 3382399 Link_out.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 7-Biopterin
  2. 7-Isobiopterin
  3. L-Erythro-7-isobiopterin
Chemical Formula C9H11N5O3
Average Molecular Weight 237.2153
Monoisotopic Molecular Weight 237.086189243
IUPAC Name 2-amino-7-(1,2-dihydroxypropyl)-1,4-dihydropteridin-4-one
Traditional IUPAC Name 2-amino-7-(1,2-dihydroxypropyl)-1H-pteridin-4-one
CAS Registry Number 2582-88-9
SMILES CC(O)C(O)C1=CN=C2C(=O)N=C(N)NC2=N1
InChI Identifier InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-5-7(12-4)13-9(10)14-8(5)17/h2-3,6,15-16H,1H3,(H3,10,12,13,14,17)
InChI Key LNXRKRFGNHXANN-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Pteridines and Derivatives
Sub Class Pterins and Derivatives
Other Descriptors
  • Pteridines and Derivatives
Substituents
  • 1,2 Diol
  • Aminopyrimidine
  • Pyrazine
  • Pyrimidine
  • Pyrimidone
  • Secondary Alcohol
Direct Parent Pterins and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 3.91 g/L ALOGPS
LogP -0.83 ALOGPS
LogP -1.2 ChemAxon
LogS -1.78 ALOGPS
pKa (strongest acidic) 7.63 ChemAxon
pKa (strongest basic) -1.3 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 133.72 A2 ChemAxon
Rotatable Bond Count 2 ChemAxon
Refractivity 58.13 ChemAxon
Polarizability 22.16 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations Not Available
Tissue Location
  • Epidermis
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022933
KNApSAcK ID Not Available
Chemspider ID 4590031 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB02263 Link_out
Metagene Link HMDB02263 Link_out
METLIN ID 6581 Link_out
PubChem Compound 5488923 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Curtius HC, Adler C, Heizmann C, Blau N, Rebrin I, Ghisla S: 7-substituted pterins: formation and occurrence. J Nutr Sci Vitaminol (Tokyo). 1992;Spec No:501-4. Pubmed: 1297797 Link_out
  2. Curtius HC, Kuster T, Matasovic A, Blau N, Dhondt JL: Primapterin, anapterin, and 6-oxo-primapterin, three new 7-substituted pterins identified in a patient with hyperphenylalaninemia. Biochem Biophys Res Commun. 1988 Jun 16;153(2):715-21. Pubmed: 3382399 Link_out
  3. Schallreuter KU, Moore J, Wood JM, Beazley WD, Peters EM, Marles LK, Behrens-Williams SC, Dummer R, Blau N, Thony B: Epidermal H(2)O(2) accumulation alters tetrahydrobiopterin (6BH4) recycling in vitiligo: identification of a general mechanism in regulation of all 6BH4-dependent processes? J Invest Dermatol. 2001 Jan;116(1):167-74. Pubmed: 11168813 Link_out
  4. Blau N, Kierat L, Matasovic A, Leimbacher W, Heizmann CW, Guardamagna O, Ponzone A: Antenatal diagnosis of tetrahydrobiopterin deficiency by quantification of pterins in amniotic fluid and enzyme activity in fetal and extrafetal tissue. Clin Chim Acta. 1994 May;226(2):159-69. Pubmed: 7923811 Link_out