NAV

2-{(9as)-9a-[(1s)-1-Hydroxyethyl]-2,7-Dimethyl-9a,10-Dihydro-5h-Pyrimido[4,5-D][1,3]Thiazolo[3,2-a]Pyrimidin-8-Yl}Ethyl Trihydrogen Diphosphate

Identification

Generic Name
2-{(9as)-9a-[(1s)-1-Hydroxyethyl]-2,7-Dimethyl-9a,10-Dihydro-5h-Pyrimido[4,5-D][1,3]Thiazolo[3,2-a]Pyrimidin-8-Yl}Ethyl Trihydrogen Diphosphate
DrugBank Accession Number
DB03361
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 468.359
Monoisotopic: 468.063357414
Chemical Formula
C14H22N4O8P2S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAcetolactate synthase, catabolicNot AvailableKlebsiella pneumoniae
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 organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organic oxoanionic compounds
Sub Class
Organic pyrophosphates
Direct Parent
Organic pyrophosphates
Alternative Parents
Secondary alkylarylamines / Monoalkyl phosphates / Pyrimidines and pyrimidine derivatives / Imidolactams / Thiazolines / Heteroaromatic compounds / Thioenol ethers / Secondary alcohols / Enamines / Azacyclic compounds
show 3 more
Substituents
Alcohol / Alkyl phosphate / Amine / Aromatic heteropolycyclic compound / Azacycle / Enamine / Heteroaromatic compound / Hydrocarbon derivative / Imidolactam / Meta-thiazoline
show 15 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
UQFVHIGKDHNMJT-XPTSAGLGSA-N
InChI
InChI=1S/C14H22N4O8P2S/c1-8-12(4-5-25-28(23,24)26-27(20,21)22)29-14(9(2)19)17-13-11(7-18(8)14)6-15-10(3)16-13/h6,9,19H,4-5,7H2,1-3H3,(H,23,24)(H,15,16,17)(H2,20,21,22)/t9-,14-/m0/s1
IUPAC Name
{[hydroxy({2-[(3S)-3-[(1S)-1-hydroxyethyl]-6,12-dimethyl-4-thia-2,7,11,13-tetraazatricyclo[7.4.0.0^{3,7}]trideca-1(13),5,9,11-tetraen-5-yl]ethoxy})phosphoryl]oxy}phosphonic acid
SMILES
[H][C@@](C)(O)[C@]12NC3=NC(C)=NC=C3CN1C(C)=C(CCOP(O)(=O)OP(O)(O)=O)S2

References

General References
Not Available
PubChem Compound
447750
PubChem Substance
46505953
ChemSpider
394759
ChEBI
43195
ZINC
ZINC000012503512
PDBe Ligand
HE3
PDB Entries
1ozg / 1ozh

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 Solubility2.87 mg/mLALOGPS
logP0.36ALOGPS
logP-3.1Chemaxon
logS-2.2ALOGPS
pKa (Strongest Acidic)-2.8Chemaxon
pKa (Strongest Basic)7.44Chemaxon
Physiological Charge-3Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area174.57 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity110.35 m3·mol-1Chemaxon
Polarizability42.33 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9768
Blood Brain Barrier+0.5751
Caco-2 permeable-0.6039
P-glycoprotein substrateSubstrate0.7951
P-glycoprotein inhibitor INon-inhibitor0.5163
P-glycoprotein inhibitor IINon-inhibitor0.7724
Renal organic cation transporterNon-inhibitor0.8201
CYP450 2C9 substrateNon-substrate0.6978
CYP450 2D6 substrateNon-substrate0.7953
CYP450 3A4 substrateSubstrate0.5197
CYP450 1A2 substrateNon-inhibitor0.6506
CYP450 2C9 inhibitorNon-inhibitor0.6633
CYP450 2D6 inhibitorNon-inhibitor0.842
CYP450 2C19 inhibitorNon-inhibitor0.6478
CYP450 3A4 inhibitorNon-inhibitor0.9128
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6069
Ames testNon AMES toxic0.6041
CarcinogenicityNon-carcinogens0.9067
BiodegradationNot ready biodegradable0.9936
Rat acute toxicity2.6729 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7194
hERG inhibition (predictor II)Non-inhibitor0.5131
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0001900000-e40b9fa32071b219a8a6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0079-0009100000-77a39b99104e62e73171
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0000900000-ff8ed26a961aaf309db8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-056r-0059000000-c849007100f868ba5a44
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00mk-7009500000-c7605b765aefe2e7c4ea
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004j-9026200000-f692ad052309ffa7244a
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]-180.19852
predicted
DeepCCS 1.0 (2019)
[M+H]+182.55652
predicted
DeepCCS 1.0 (2019)
[M+Na]+188.64967
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Acetolactate synthase, catabolic
Kind
Protein
Organism
Klebsiella pneumoniae
Pharmacological action
Unknown
General Function
Thiamine pyrophosphate binding
Specific Function
Not Available
Gene Name
budB
Uniprot ID
P27696
Uniprot Name
Acetolactate synthase, catabolic
Molecular Weight
60337.52 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 June 12, 2020 16:52