Identification
NameL-erythro-7,8-dihydrobiopterin
Accession NumberDB04400  (EXPT01697, DB03271, EXPT01698)
TypeSmall Molecule
GroupsExperimental
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.

Structure
Thumb
Synonyms
Dihydrobiopterin
L-erythro-q-Dihydrobiopterin
q-BH2
Quinonoid dihydrobiopterin
External IDs HBL
Product Ingredients 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
Categories
UNIINot Available
CAS number6779-87-9
WeightAverage: 239.2312
Monoisotopic: 239.101839307
Chemical FormulaC9H13N5O3
InChI KeyFEMXZDUTFRTWPE-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
(1R,2S)-1-(4-hydroxy-2-imino-1,2,7,8-tetrahydropteridin-6-yl)propane-1,2-diol
SMILES
[H][C@@](C)(O)[C@]([H])(O)C1=NC2=C(NC1)NC(=N)N=C2O
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Phenylalanine-4-hydroxylaseProteinunknownNot AvailableHumanP00439 details
Pteridine reductase 1ProteinunknownNot AvailableLeishmania majorQ01782 details
Nitric oxide synthase, inducibleProteinunknownNot AvailableHumanP35228 details
Tyrosine 3-monooxygenaseProteinunknownNot AvailableHumanP07101 details
Pterin-4-alpha-carbinolamine dehydrataseProteinunknownNot AvailableHumanP61457 details
Dihydroneopterin aldolaseProteinunknownNot AvailableStaphylococcus aureusP56740 details
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
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.826 mg/mLALOGPS
logP-1.1ALOGPS
logP-3.1ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)-2.4ChemAxon
pKa (Strongest Basic)14.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area133.32 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.13 m3·mol-1ChemAxon
Polarizability22.91 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET featuresNot Available
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPteridines and derivatives
Direct ParentBiopterins and derivatives
Alternative ParentsSecondary alkylarylamines / Hydroxypyrimidines / Heteroaromatic compounds / Secondary alcohols / Ketimines / 1,2-diols / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
SubstituentsBiopterin / Secondary aliphatic/aromatic amine / Hydroxypyrimidine / Pyrimidine / Heteroaromatic compound / 1,2-diol / Ketimine / Secondary alcohol / Propargyl-type 1,3-dipolar organic compound / Organic 1,3-dipolar compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors7,8-dihydrobiopterin (CHEBI:43029 )

Targets

Kind
Protein
Organism
Human
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. Confers resistance to methotrexate (MTX).
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
Human
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 and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2. As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-n...
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
Human
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
Human
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. Regulates the dimerization of homeodomain protein HNF1A and enhances its transcriptional activity.
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
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 August 02, 2017 17:00