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Identification
NameBiopterin
Accession NumberDB03886  (EXPT00708)
TypeSmall Molecule
GroupsExperimental
Description

A natural product that has been considered as a growth factor for some insects. [PubChem]

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIE54CTM794Y
CAS numberNot Available
WeightAverage: 237.2153
Monoisotopic: 237.086189243
Chemical FormulaC9H11N5O3
InChI KeyInChIKey=LHQIJBMDNUYRAM-AWFVSMACSA-N
InChI
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-/m1/s1
IUPAC Name
2-amino-6-[(1S,2R)-1,2-dihydroxypropyl]-3,4-dihydropteridin-4-one
SMILES
C[C@@H](O)[C@@H](O)C1=CN=C2N=C(N)NC(=O)C2=N1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentBiopterins and derivatives
Alternative Parents
Substituents
  • Biopterin
  • Pyrimidone
  • Pyrimidine
  • Pyrazine
  • Primary aromatic amine
  • Heteroaromatic compound
  • Vinylogous amide
  • Secondary alcohol
  • 1,2-diol
  • Azacycle
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9951
Blood Brain Barrier+0.7679
Caco-2 permeable-0.5874
P-glycoprotein substrateSubstrate0.5568
P-glycoprotein inhibitor INon-inhibitor0.9432
P-glycoprotein inhibitor IINon-inhibitor0.9919
Renal organic cation transporterNon-inhibitor0.9405
CYP450 2C9 substrateNon-substrate0.7904
CYP450 2D6 substrateNon-substrate0.7902
CYP450 3A4 substrateNon-substrate0.6253
CYP450 1A2 substrateNon-inhibitor0.864
CYP450 2C9 inhibitorNon-inhibitor0.8396
CYP450 2D6 inhibitorNon-inhibitor0.9058
CYP450 2C19 inhibitorNon-inhibitor0.7536
CYP450 3A4 inhibitorNon-inhibitor0.9226
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9576
Ames testNon AMES toxic0.6053
CarcinogenicityNon-carcinogens0.9307
BiodegradationNot ready biodegradable0.9912
Rat acute toxicity2.4048 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9895
hERG inhibition (predictor II)Non-inhibitor0.9031
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.71 mg/mLALOGPS
logP-1.1ALOGPS
logP-1.7ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)9.99ChemAxon
pKa (Strongest Basic)1.05ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.72 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity58.57 m3·mol-1ChemAxon
Polarizability22.41 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Hayashi Uchino, Masaaki Azuma, Takehisa Ohashi, Kiyoshi Watanabe, “Sulfate of 5,6,7,8-tetrahydro-L-erythro-biopterin and process for preparing the same.” U.S. Patent US4649197, issued November, 1952.

US4649197
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Sepiapterin reductase activity
Specific Function:
Catalyzes the final one or two reductions in tetra-hydrobiopterin biosynthesis to form 5,6,7,8-tetrahydrobiopterin.
Gene Name:
SPR
Uniprot ID:
P35270
Molecular Weight:
28048.13 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Metal ion binding
Specific Function:
Involved in the biosynthesis of tetrahydrobiopterin, an essential cofactor of aromatic amino acid hydroxylases. Catalyzes the transformation of 7,8-dihydroneopterin triphosphate into 6-pyruvoyl tetrahydropterin.
Gene Name:
PTS
Uniprot ID:
Q03393
Molecular Weight:
16385.63 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Nadph binding
Specific Function:
Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA precursor synthesis. Binds its own mRNA and that of DHFRL1.
Gene Name:
DHFR
Uniprot ID:
P00374
Molecular Weight:
21452.61 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23