Biopterin

Identification

Name
Biopterin
Accession Number
DB03886  (EXPT00708)
Type
Small Molecule
Groups
Experimental
Description

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

Structure
Thumb
Synonyms
Not Available
Categories
UNII
E54CTM794Y
CAS number
Not Available
Weight
Average: 237.2153
Monoisotopic: 237.086189243
Chemical Formula
C9H11N5O3
InChI Key
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USepiapterin reductaseNot AvailableHuman
U6-pyruvoyl tetrahydrobiopterin synthaseNot AvailableHuman
UDihydrofolate reductaseNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not 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 References
Not Available
External Links
KEGG Compound
C06313
PubChem Compound
444475
PubChem Substance
46505723
ChemSpider
392400
ChEBI
41183
HET
BIO
Wikipedia
Biopterin
PDB Entries
1b66 / 1sep / 1y13 / 2a0s / 2bd0 / 3qna

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pteridines and derivatives
Sub Class
Pterins and derivatives
Direct Parent
Biopterins and derivatives
Alternative Parents
Pyrimidones / Aminopyrimidines and derivatives / Pyrazines / Vinylogous amides / Heteroaromatic compounds / Secondary alcohols / 1,2-diols / Azacyclic compounds / Primary amines / Organopnictogen compounds
show 3 more
Substituents
Biopterin / Aminopyrimidine / Pyrimidone / Pyrazine / Pyrimidine / Heteroaromatic compound / Vinylogous amide / 1,2-diol / Secondary alcohol / Azacycle
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
biopterin (CHEBI:41183)

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
Uniprot Name
Sepiapterin reductase
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 tet...
Gene Name
PTS
Uniprot ID
Q03393
Uniprot Name
6-pyruvoyl tetrahydrobiopterin synthase
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 pre...
Gene Name
DHFR
Uniprot ID
P00374
Uniprot Name
Dihydrofolate reductase
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]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:46