Identification
- Generic Name
- Biopterin
- DrugBank Accession Number
- DB03886
- Background
A natural product that has been considered as a growth factor for some insects. [PubChem]
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Biopterin (DB03886)
- Weight
- Average: 237.2153
Monoisotopic: 237.086189243 - Chemical Formula
- C9H11N5O3
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism USepiapterin reductase Not Available Humans U6-pyruvoyl tetrahydrobiopterin synthase Not Available Humans UDihydrofolate reductase Not Available Humans - 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,2-diol / Alcohol / Amine / Aminopyrimidine / Aromatic alcohol / Aromatic heteropolycyclic compound / Azacycle / Biopterin / Heteroaromatic compound / Hydrocarbon derivative show 12 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- biopterin (CHEBI:41183)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- E54CTM794Y
- CAS number
- Not Available
- 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
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
- PDB Entries
- 1b66 / 1sep / 1y13 / 2a0s / 2bd0 / 3qna
Clinical Trials
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
Property Value Source Water Solubility 3.71 mg/mL ALOGPS logP -1.1 ALOGPS logP -1.7 Chemaxon logS -1.8 ALOGPS pKa (Strongest Acidic) 9.99 Chemaxon pKa (Strongest Basic) -0.66 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 133.72 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 58.57 m3·mol-1 Chemaxon Polarizability 22.41 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9951 Blood Brain Barrier + 0.7679 Caco-2 permeable - 0.5874 P-glycoprotein substrate Substrate 0.5568 P-glycoprotein inhibitor I Non-inhibitor 0.9432 P-glycoprotein inhibitor II Non-inhibitor 0.9919 Renal organic cation transporter Non-inhibitor 0.9405 CYP450 2C9 substrate Non-substrate 0.7904 CYP450 2D6 substrate Non-substrate 0.7902 CYP450 3A4 substrate Non-substrate 0.6253 CYP450 1A2 substrate Non-inhibitor 0.864 CYP450 2C9 inhibitor Non-inhibitor 0.8396 CYP450 2D6 inhibitor Non-inhibitor 0.9058 CYP450 2C19 inhibitor Non-inhibitor 0.7536 CYP450 3A4 inhibitor Non-inhibitor 0.9226 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9576 Ames test Non AMES toxic 0.6053 Carcinogenicity Non-carcinogens 0.9307 Biodegradation Not ready biodegradable 0.9912 Rat acute toxicity 2.4048 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9895 hERG inhibition (predictor II) Non-inhibitor 0.9031
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52