NAV

2-Acetyl-3-[(4-Amino-2-Methyl-5-Pyrimidinyl)Methyl]-4-Methyl-5-(4,6,6-Trihydroxy-3,5-Dioxa-4,6-Diphosphahex-1-Yl)Thiazolium Inner Salt P,P'-Dioxide

Identification

Generic Name
2-Acetyl-3-[(4-Amino-2-Methyl-5-Pyrimidinyl)Methyl]-4-Methyl-5-(4,6,6-Trihydroxy-3,5-Dioxa-4,6-Diphosphahex-1-Yl)Thiazolium Inner Salt P,P'-Dioxide
DrugBank Accession Number
DB02410
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 467.351
Monoisotopic: 467.055532382
Chemical Formula
C14H21N4O8P2S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UPyruvate-flavodoxin oxidoreductaseNot AvailableDesulfovibrio africanus
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 thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Thiamine phosphates
Alternative Parents
Organic pyrophosphates / Aryl alkyl ketones / 2,4,5-trisubstituted thiazoles / Monoalkyl phosphates / Aminopyrimidines and derivatives / Imidolactams / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds
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Substituents
2,4,5-trisubstituted 1,3-thiazole / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteromonocyclic compound / Aryl alkyl ketone / Aryl ketone / Azacycle / Azole / Heteroaromatic compound
show 17 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
GYRGKLZCJRVYRV-UHFFFAOYSA-O
InChI
InChI=1S/C14H20N4O8P2S/c1-8-12(4-5-25-28(23,24)26-27(20,21)22)29-14(9(2)19)18(8)7-11-6-16-10(3)17-13(11)15/h6H,4-5,7H2,1-3H3,(H4-,15,16,17,20,21,22,23,24)/p+1
IUPAC Name
2-acetyl-3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium
SMILES
CC(=O)C1=[N+](CC2=CN=C(C)N=C2N)C(C)=C(CCOP(O)(=O)OP(O)(O)=O)S1

References

General References
Not Available
PubChem Compound
4369479
PubChem Substance
46504515
ChemSpider
3572025
ZINC
ZINC000013546639
PDBe Ligand
HTL
PDB Entries
1kek / 1v5g / 2c3y / 2ezu / 2uza / 3ahd / 3ahh / 3ahi / 6bd3 / 6cip …
show 3 more

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 Solubility0.0596 mg/mLALOGPS
logP-0.19ALOGPS
logP-7Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)1.78Chemaxon
pKa (Strongest Basic)6.48Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count9Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area186.04 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity105.21 m3·mol-1Chemaxon
Polarizability40.57 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9988
Blood Brain Barrier+0.7835
Caco-2 permeable-0.5947
P-glycoprotein substrateSubstrate0.5377
P-glycoprotein inhibitor INon-inhibitor0.883
P-glycoprotein inhibitor IINon-inhibitor0.7589
Renal organic cation transporterNon-inhibitor0.8768
CYP450 2C9 substrateNon-substrate0.7582
CYP450 2D6 substrateNon-substrate0.8123
CYP450 3A4 substrateNon-substrate0.5994
CYP450 1A2 substrateNon-inhibitor0.7429
CYP450 2C9 inhibitorNon-inhibitor0.7257
CYP450 2D6 inhibitorNon-inhibitor0.8682
CYP450 2C19 inhibitorNon-inhibitor0.6896
CYP450 3A4 inhibitorNon-inhibitor0.9184
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7645
Ames testNon AMES toxic0.6027
CarcinogenicityNon-carcinogens0.9032
BiodegradationReady biodegradable0.5186
Rat acute toxicity2.6420 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.918
hERG inhibition (predictor II)Non-inhibitor0.5873
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 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-177.2338
predicted
DeepCCS 1.0 (2019)
[M+H]+179.59178
predicted
DeepCCS 1.0 (2019)
[M+Na]+187.75194
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Pyruvate-flavodoxin oxidoreductase
Kind
Protein
Organism
Desulfovibrio africanus
Pharmacological action
Unknown
General Function
Thiamine pyrophosphate binding
Specific Function
Catalyzes the ferredoxin-dependent oxidative decarboxylation of pyruvate. Required for the transfer of electrons from pyruvate to ferredoxin (PubMed:9294422, PubMed:7612653). Ferredoxin I and ferre...
Gene Name
por
Uniprot ID
P94692
Uniprot Name
Pyruvate synthase
Molecular Weight
133679.405 Da

Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:16