| Common Name |
D-Biopterin
| Description |
D-Biopterin is a pterin which is a chemical compound composed of a pyrazine ring and a pyrimidine ring. The level of biopterin decreases in the urine of patients with guanosine triphosphate cyclohydrolase I. (PMID 10770663 ).
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
| Synonyms |
| Value |
Source |
(-)-BiopterinChEBI
(1'r,1's) BiopterinHMDB
2-amino-6-(L-erythro-1,2-Dihydroxypropyl)-4(3H)-pteridinoneHMDB
6-BiopterinHMDB
L-BiopterinHMDB
L-erythro-BiopterinHMDB
Pterin H b2HMDB
[S-(R*,s*)]-2-amino-6-(1,2-dihydroxypropyl)-4(1H)-pteridinoneHMDB
OrinapterinMeSH
DictyopterinMeSH
2-amino-6-(1,2-Dihydroxypropyl)-4(1H)-pteridinoneMeSH
| Chemical Formlia |
C9H11N5O3
| Average Molecliar Weight |
237.2153
| Monoisotopic Molecliar Weight |
237.086189243
| IUPAC Name |
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4-dihydropteridin-4-one
| Traditional Name |
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1H-pteridin-4-one
| CAS Registry Number |
13039-62-8
| SMILES |
C[C@H](O)[C@H](O)C1=NC2=C(NC(N)=NC2=O)N=C1
| InChI Identifier |
InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h2-3,6,15-16H,1H3,(H3,10,11,13,14,17)/t3-,6-/m0/s1
| InChI Key |
LHQIJBMDNUYRAM-DZSWIPIPSA-N
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities known as biopterins and derivatives. These are coenzymes containing a 2-amino-pteridine-4-one derivative. They are mainly synthesized in several parts of the body, including the pineal gland.
| Kingdom |
Chemical entities
| Super Class |
Organic compounds
| Class |
Organoheterocyclic compounds
| Sub Class |
Pteridines and derivatives
| Direct Parent |
Biopterins and derivatives
| Alternative Parents |
Pyrimidones
Aminopyrimidines and derivatives
Pyrazines
Primary aromatic amines
Vinylogous amides
Heteroaromatic compounds
Secondary alcohols
1,2-diols
Azacyclic compounds
Organopnictogen compounds
Organic oxides
Hydrocarbon derivatives
Aromatic alcohols
| Substituents |
Biopterin
Aminopyrimidine
Pyrimidone
Primary aromatic amine
Pyrazine
Pyrimidine
Vinylogous amide
Heteroaromatic compound
Secondary alcohol
1,2-diol
Azacycle
Organic oxide
Amine
Alcohol
Organopnictogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound
| Molecliar Framework |
Aromatic heteropolycyclic compounds
| External Descriptors |
biopterin (CHEBI:63931 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
| Biofunction |
Not Available
| Application |
Not Available
| Cellliar locations |
Not Available
| Physical Properties |
| State |
Solid
| Experimental Properties |
| Property |
Value |
Reference |
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility4.06 mg/mLALOGPS
logP-0.87ALOGPS
logP-1.2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)7.6ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.72 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.13 m3·mol-1ChemAxon
Polarizability22.41 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| GC-MS |
GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0aos-1922500000-07177d5a450dbf7c637aView in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 10V, Positive (Annotated)splash10-000i-0190000000-cea25aa8258af5c9e837View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 25V, Positive (Annotated)splash10-004i-0900000000-32102578ef16c3df8f17View in MoNA
| LC-MS/MS |
LC-MS/MS Spectrum – Quattro_QQQ 40V, Positive (Annotated)splash10-0a5c-5900000000-441b149b7ee5432cdac3View in MoNA
| 1D NMR |
1H NMR SpectrumNot Available
| 2D NMR |
[1H,13C] 2D NMR SpectrumNot Available
| Biological Properties |
| Cellliar 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
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB022154
| KNApSAcK ID |
Not Available
| Chemspider ID |
392400
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Not Available
| NuGOwiki Link |
HMDB00633
| Metagene Link |
HMDB00633
| METLIN ID |
5606
| PubChem Compound |
444475
| PDB ID |
BIO
| ChEBI ID |
41183
Product: GNE-495
References |
| Synthesis Reference |
Andrews, Kenneth J. M.; Barber, W. E.; Tong, B. P. Synthesis of biopterin. Journal of the Chemical Society [Section] C: Organic (1969), (6), 928-30. |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- Coskun T, Karagoz T, Kalkanoglu S, Tokatli A, Ozalp I, Thony B, Blau N: Guanosine triphosphate cyclohydrolase I deficiency: a rare cause of hyperphenylalaninemia. Turk J Pediatr. 1999 Apr-Jun;41(2):231-7. [PubMed:10770663 ]
|
PMID: 19430615