DrugBank: 7,8-Dihydrobiopterin (DB04400)

targets (6)

Identification

Name

7,8-Dihydrobiopterin

Accession Number

DB04400 (DB03271, EXPT01697)

Type

small molecule

Groups

experimental

Description

7,8-dihydrobiopterin is an inhibitor of the enzyme dihydroneopterin aldolase (DHNA), which catalyzes the conversion of 7,8-dihydroneopterin to 6-hydroxymethyl-7,8-dihydropterin and glycolaldehyde.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

7,8-Dihydro-L-Biopterin
HBI
HBL
L-erythro-7,8-Dihydrobiopterin
L-erythro-dihydrobiopterin
L-erythro-q-dihydrobiopterin
q-BH2
quinonoid dihydrobiopterin

Salts

Not Available

Brand names

Not Available

Brand mixtures

Not Available

Categories

Not Available

CAS number

6779-87-9

Weight

Average: 239.2312
Monoisotopic: 239.101839307

Chemical Formula

C₉H₁₃N₅O₃

InChI Key

InChIKey=FEMXZDUTFRTWPE-AWFVSMACSA-N

InChI

InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,6,15-16H,2H2,1H3,(H4,10,11,13,14,17)/t3-,6-/m1/s1

Plain Text

IUPAC Name

2-amino-6-[(1S,2R)-1,2-dihydroxypropyl]-3,4,7,8-tetrahydropteridin-4-one

SMILES

C[C@@H](O)[C@@H](O)C1=NC2=C(NC1)N=C(N)NC2=O

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

Not Available

Pharmacodynamics

Not Available

Mechanism of action

Not Available

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

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	1.63e+00 g/l	ALOGPS
logP	-1.6	ALOGPS
logP	-1.9	ChemAxon
logS	-2.2	ALOGPS
pKa (strongest acidic)	10.81	ChemAxon
pKa (strongest basic)	3.67	ChemAxon
physiological charge	0	ChemAxon
hydrogen acceptor count	7	ChemAxon
hydrogen donor count	5	ChemAxon
polar surface area	132.33	ChemAxon
rotatable bond count	2	ChemAxon
refractivity	68.31	ChemAxon
polarizability	23.11	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Compound	C02953
PubChem Compound	5460203
PubChem Substance	46508233
ChemSpider	247
ChEBI	15375
ChEMBL	15375
HET	HBI

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

1DMW
1MLW

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Tyrosine 3-monooxygenase Pharmacological action: unknown Plays an important role in the physiology of adrenergic neurons Organism class: human UniProt ID: P07101 Gene: TH Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 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 2. Pterin-4-alpha-carbinolamine dehydratase Pharmacological action: unknown Organism class: human UniProt ID: P61457 Gene: PCBD1 SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 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 3. Phenylalanine-4-hydroxylase Pharmacological action: unknown Organism class: human UniProt ID: P00439 Gene: PAH Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 4. Pteridine reductase 1 Pharmacological action: unknown Exhibits a NADPH-dependent biopterin reductase activity. Has good activity with folate and significant activity with dihydrofolate and dihydrobiopterin, but not with quinonoid dihydrobiopterin. Confers resistance to methotrexate (MTX) Organism class: parasitic UniProt ID: Q01782 Gene: PTR1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 5. Nitric oxide synthase, inducible Pharmacological action: unknown Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions Organism class: human UniProt ID: P35228 Gene: NOS2A Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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 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 6. Dihydroneopterin aldolase Pharmacological action: unknown Catalyzes the conversion of 7,8-dihydroneopterin to 6- hydroxymethyl-7,8-dihydropterin Organism class: bacterial UniProt ID: P56740 Gene: folB Protein Sequence: FASTA SNPs: SNPJam Report References: Deng H, Callender R, Dale GE: A vibrational structure of 7,8-dihydrobiopterin bound to dihydroneopterin aldolase. J Biol Chem. 2000 Sep 29;275(39):30139-43. Pubmed

Targets

1. Tyrosine 3-monooxygenase

Pharmacological action: unknown

Plays an important role in the physiology of adrenergic neurons

Organism class: human
UniProt ID: P07101 Link_out

Gene: TH

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
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

2. Pterin-4-alpha-carbinolamine dehydratase

Pharmacological action: unknown
Organism class: human
UniProt ID: P61457 Link_out

Gene: PCBD1
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
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

3. Phenylalanine-4-hydroxylase

Pharmacological action: unknown
Organism class: human
UniProt ID: P00439 Link_out

Gene: PAH

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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

4. Pteridine reductase 1

Pharmacological action: unknown

Exhibits a NADPH-dependent biopterin reductase activity. Has good activity with folate and significant activity with dihydrofolate and dihydrobiopterin, but not with quinonoid dihydrobiopterin. Confers resistance to methotrexate (MTX)

Organism class: parasitic
UniProt ID: Q01782 Link_out

Gene: PTR1
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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

5. Nitric oxide synthase, inducible

Pharmacological action: unknown

Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions

Organism class: human
UniProt ID: P35228 Link_out

Gene: NOS2A Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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
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

6. Dihydroneopterin aldolase

Pharmacological action: unknown

Catalyzes the conversion of 7,8-dihydroneopterin to 6- hydroxymethyl-7,8-dihydropterin

Organism class: bacterial
UniProt ID: P56740 Link_out

Gene: folB
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Deng H, Callender R, Dale GE: A vibrational structure of 7,8-dihydrobiopterin bound to dihydroneopterin aldolase. J Biol Chem. 2000 Sep 29;275(39):30139-43. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:23