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Human Metabolome Database Version 3.5

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Showing metabocard for O2'-4a-cyclic-tetrahydrobiopterin (HMDB13031)

Record Information
Version 3.5
Creation Date 2009-07-24 18:11:58 -0600
Update Date 2013-05-13 17:09:28 -0600
HMDB ID HMDB13031
Secondary Accession Numbers None
Metabolite Identification
Common Name O2'-4a-cyclic-tetrahydrobiopterin
Description O2'-4a-cyclic-tetrahydrobiopterin is a novel pterin intermediate, in addition to the expected 4a-hydroxytetrahydrobiopterin (4a-OH-BH4) and quinonoid dihydrobiopterin generated during catalytic turnover of tyrosine hydroxylase (TH) with tetrahydrobiopterin as the cofactor. Its conversion into quinonoid dihydrobiopterin is catalysed by pterin-4a-carbinolamine dehydratase.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 4a-Cyc-BH(,4)
  2. 4a-Cyclic-tetrahydrobiopterin
Chemical Formula C9H13N5O3
Average Molecular Weight 239.2312
Monoisotopic Molecular Weight 239.101839307
IUPAC Name (10R,11R)-4-amino-10-hydroxy-11-methyl-12-oxa-3,5,7,13-tetraazatricyclo[7.3.1.0^{1,6}]trideca-3,5-dien-2-one
Traditional IUPAC Name (10R,11R)-4-amino-10-hydroxy-11-methyl-12-oxa-3,5,7,13-tetraazatricyclo[7.3.1.0^{1,6}]trideca-3,5-dien-2-one
CAS Registry Number Not Available
SMILES C[C@H]1OC23NC(CNC2=NC(N)=NC3=O)[C@H]1O
InChI Identifier InChI=1S/C9H13N5O3/c1-3-5(15)4-2-11-6-9(14-4,17-3)7(16)13-8(10)12-6/h3-5,14-15H,2H2,1H3,(H3,10,11,12,13,16)/t3-,4?,5+,9?/m1/s1
InChI Key JZTDUNXDDUJXRZ-UPYOWCHBSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Heteropolycyclic Compounds
Class Pteridines and Derivatives
Sub Class Pterins and Derivatives
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Aminoalcohol
  • 5,6 Dihydropyrimidine
  • Carboxamide Group
  • Carboxylic Acid Amidine
  • Guanidine
  • Hemiaminal
  • Hydropyrimidine
  • Oxazinane
  • Piperazine
  • 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 Not Available
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 6.17 g/L ALOGPS
LogP -1.67 ALOGPS
LogP -2 ChemAxon
LogS -1.59 ALOGPS
pKa (strongest acidic) 13.57 ChemAxon
pKa (strongest basic) 3.6 ChemAxon
Hydrogen Acceptor Count 8 ChemAxon
Hydrogen Donor Count 4 ChemAxon
Polar Surface Area 121.33 A2 ChemAxon
Rotatable Bond Count 0 ChemAxon
Refractivity 55.09 ChemAxon
Polarizability 22.18 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
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 FDB029257
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB13031 Link_out
Metagene Link HMDB13031 Link_out
METLIN ID Not Available
PubChem Compound 53481588 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available