L-erythro-7,8-dihydrobiopterin

Identification

Name
L-erythro-7,8-dihydrobiopterin
Accession Number
DB04400
Description

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

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 239.2312
Monoisotopic: 239.101839307
Chemical Formula
C9H13N5O3
Synonyms
  • Dihydrobiopterin
  • L-erythro-q-Dihydrobiopterin
  • q-BH2
  • Quinonoid dihydrobiopterin
External IDs
  • HBL

Pharmacology

Indication
Not Available
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UTyrosine 3-monooxygenaseNot AvailableHumans
UPterin-4-alpha-carbinolamine dehydrataseNot AvailableHumans
UPhenylalanine-4-hydroxylaseNot AvailableHumans
UPteridine reductase 1Not AvailableLeishmania major
UNitric oxide synthase, inducibleNot AvailableHumans
UDihydroneopterin aldolaseNot AvailableStaphylococcus aureus
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
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
Affected organisms
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

Products

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
Secondary alkylarylamines / Hydroxypyrimidines / Heteroaromatic compounds / Secondary alcohols / Ketimines / 1,2-diols / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
1,2-diol / Alcohol / Amine / Aromatic heteropolycyclic compound / Azacycle / Biopterin / Heteroaromatic compound / Hydrocarbon derivative / Hydroxypyrimidine / Imine
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
7,8-dihydrobiopterin (CHEBI:43029)

Chemical Identifiers

UNII
Not Available
CAS number
6779-87-9
InChI Key
FEMXZDUTFRTWPE-DZSWIPIPSA-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-/m0/s1
IUPAC Name
2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,7,8-tetrahydropteridin-4-one
SMILES
C[C@H](O)[C@H](O)C1=NC2=C(NC1)NC(N)=NC2=O

References

General References
Not Available
PubChem Compound
119055
PubChem Substance
46508233
ChemSpider
106382
ChEBI
43029
ZINC
ZINC000018181336
PDBe Ligand
HBI
PDB Entries
1dcp / 1dmw / 1dr1 / 1dr3 / 1dr4 / 1dr6 / 1e92 / 1jwk / 1lrm / 1ltz
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Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility1.63 mg/mLALOGPS
logP-1.4ALOGPS
logP-2.3ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)12.98ChemAxon
pKa (Strongest Basic)3.73ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area132.33 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.11 m3·mol-1ChemAxon
Polarizability23.1 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

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

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tyrosine 3-monooxygenase activity
Specific Function
Plays an important role in the physiology of adrenergic neurons.
Gene Name
TH
Uniprot ID
P07101
Uniprot Name
Tyrosine 3-monooxygenase
Molecular Weight
58599.545 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
Humans
Pharmacological action
Unknown
General Function
Transcription coactivator activity
Specific Function
Involved in tetrahydrobiopterin biosynthesis. Seems to both prevent the formation of 7-pterins and accelerate the formation of quinonoid-BH2. Coactivator for HNF1A-dependent transcription. Regulate...
Gene Name
PCBD1
Uniprot ID
P61457
Uniprot Name
Pterin-4-alpha-carbinolamine dehydratase
Molecular Weight
11999.515 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
Humans
Pharmacological action
Unknown
General Function
Phenylalanine 4-monooxygenase activity
Specific Function
Not Available
Gene Name
PAH
Uniprot ID
P00439
Uniprot Name
Phenylalanine-4-hydroxylase
Molecular Weight
51861.565 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]
Kind
Protein
Organism
Leishmania major
Pharmacological action
Unknown
General Function
Thymidylate synthase activity
Specific Function
Exhibits a NADPH-dependent biopterin reductase activity. Has good activity with folate and significant activity with dihydrofolate and dihydrobiopterin, but not with quinonoid dihydrobiopterin. Con...
Gene Name
PTR1
Uniprot ID
Q01782
Uniprot Name
Pteridine reductase 1
Molecular Weight
30456.315 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Tetrahydrobiopterin binding
Specific Function
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity ...
Gene Name
NOS2
Uniprot ID
P35228
Uniprot Name
Nitric oxide synthase, inducible
Molecular Weight
131116.3 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
Staphylococcus aureus
Pharmacological action
Unknown
General Function
Isomerase activity
Specific Function
Catalyzes the conversion of 7,8-dihydroneopterin to 6-hydroxymethyl-7,8-dihydropterin. Can also catalyze the epimerization of carbon 2' of dihydroneopterin to dihydromonapterin.
Gene Name
folB
Uniprot ID
P56740
Uniprot Name
Dihydroneopterin aldolase
Molecular Weight
13750.58 Da
References
  1. 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:10896664]

Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:52

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