NAV

Quinonoid 7,8-Tetrahydrobiopterin

Identification

Generic Name
Quinonoid 7,8-Tetrahydrobiopterin
DrugBank Accession Number
DB02562
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 239.2312
Monoisotopic: 239.101839307
Chemical Formula
C9H13N5O3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPhenylalanine-4-hydroxylaseNot AvailableHumans
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
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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
Not Available
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 / Imidolactams / Vinylogous amides / Heteroaromatic compounds / Secondary alcohols / 1,2-diols / Azacyclic compounds / Primary amines / Organopnictogen compounds
show 2 more
Substituents
1,2-diol / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Biopterin / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
79647-29-3
InChI Key
ZHQJVZLJDXWFFX-RPDRRWSUSA-N
InChI
InChI=1S/C9H13N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3-4,6,15-16H,2H2,1H3,(H3,10,11,13,14,17)/t3-,4+,6-/m0/s1
IUPAC Name
(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-1,4,6,7-tetrahydropteridin-4-one
SMILES
[H][C@@]1(CN=C2NC(N)=NC(=O)C2=N1)[C@@H](O)[C@H](C)O

References

General References
Not Available
Human Metabolome Database
HMDB0002215
KEGG Compound
C00268
PubChem Compound
133246
PubChem Substance
46506636
ChemSpider
117564
ChEBI
43120
PDBe Ligand
H2B
PDB Entries
1dww / 1tg2 / 2fbz / 2v6t / 4cx1 / 4cx2 / 4nos

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 Solubility1.45 mg/mLALOGPS
logP-1.4ALOGPS
logP-2Chemaxon
logS-2.2ALOGPS
pKa (Strongest Acidic)10.22Chemaxon
pKa (Strongest Basic)2.58Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area132.66 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity57.03 m3·mol-1Chemaxon
Polarizability22.77 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9871
Blood Brain Barrier+0.5367
Caco-2 permeable-0.6681
P-glycoprotein substrateSubstrate0.7297
P-glycoprotein inhibitor INon-inhibitor0.9025
P-glycoprotein inhibitor IINon-inhibitor0.9294
Renal organic cation transporterNon-inhibitor0.7915
CYP450 2C9 substrateNon-substrate0.8026
CYP450 2D6 substrateNon-substrate0.7728
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.8603
CYP450 2C9 inhibitorNon-inhibitor0.8954
CYP450 2D6 inhibitorNon-inhibitor0.913
CYP450 2C19 inhibitorNon-inhibitor0.8705
CYP450 3A4 inhibitorNon-inhibitor0.9665
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9788
Ames testNon AMES toxic0.5683
CarcinogenicityNon-carcinogens0.9322
BiodegradationNot ready biodegradable0.9703
Rat acute toxicity2.5041 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.994
hERG inhibition (predictor II)Non-inhibitor0.771
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-MSsplash10-006y-9720000000-50fd5953817583278634
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-58d8d3f103886d7c7713
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-0910000000-5c3778c99301b3422cca
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0290000000-6276844284cd30576bb8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0910000000-dd8b692cb9afbf82c9ba
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-3900000000-3b90d42290e6fba7f631
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014l-6900000000-977982c900c1ec6ef47f
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-160.8608328
predicted
DarkChem Lite v0.1.0
[M-H]-150.6161
predicted
DeepCCS 1.0 (2019)
[M+H]+157.8638328
predicted
DarkChem Lite v0.1.0
[M+H]+153.01166
predicted
DeepCCS 1.0 (2019)
[M+Na]+158.5407328
predicted
DarkChem Lite v0.1.0
[M+Na]+159.83714
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Phenylalanine-4-hydroxylase
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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at August 01, 2020 13:43