Phosphonoacetic Acid

Identification

Name
Phosphonoacetic Acid
Accession Number
DB02823  (EXPT02488)
Type
Small Molecule
Groups
Experimental
Description

A simple organophosphorus compound that inhibits DNA polymerase, especially in viruses and is used as an antiviral agent. [PubChem]

Structure
Thumb
Synonyms
Not Available
Categories
UNII
N919E46723
CAS number
4408-78-0
Weight
Average: 140.0319
Monoisotopic: 139.987459782
Chemical Formula
C2H5O5P
InChI Key
XUYJLQHKOGNDPB-UHFFFAOYSA-N
InChI
InChI=1S/C2H5O5P/c3-2(4)1-8(5,6)7/h1H2,(H,3,4)(H2,5,6,7)
IUPAC Name
2-phosphonoacetic acid
SMILES
OC(=O)CP(O)(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAlkaline phosphataseNot AvailableEscherichia coli (strain K12)
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0004110
KEGG Compound
C05682
PubChem Compound
546
PubChem Substance
46506487
ChemSpider
531
BindingDB
50008089
ChEBI
15732
ChEMBL
CHEMBL50300
HET
PAE
PDB Entries
1ew8 / 1vq7 / 3t02 / 3tw6 / 4i3x

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)143-146 °CPhysProp
water solubility3.92E+005 mg/L (at 0 °C)STEPHEN,H & STEPHEN,T (1963)
Predicted Properties
PropertyValueSource
Water Solubility25.1 mg/mLALOGPS
logP-2.6ALOGPS
logP-1.6ChemAxon
logS-0.75ALOGPS
pKa (Strongest Acidic)1.64ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.63 m3·mol-1ChemAxon
Polarizability9.63 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9131
Blood Brain Barrier+0.9391
Caco-2 permeable-0.7795
P-glycoprotein substrateNon-substrate0.8043
P-glycoprotein inhibitor INon-inhibitor0.9741
P-glycoprotein inhibitor IINon-inhibitor0.9948
Renal organic cation transporterNon-inhibitor0.9625
CYP450 2C9 substrateNon-substrate0.7976
CYP450 2D6 substrateNon-substrate0.858
CYP450 3A4 substrateNon-substrate0.7198
CYP450 1A2 substrateNon-inhibitor0.9396
CYP450 2C9 inhibitorNon-inhibitor0.9416
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9388
CYP450 3A4 inhibitorNon-inhibitor0.9434
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9943
Ames testNon AMES toxic0.9093
CarcinogenicityNon-carcinogens0.533
BiodegradationReady biodegradable0.5985
Rat acute toxicity1.8913 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9512
hERG inhibition (predictor II)Non-inhibitor0.9688
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
GC-MS Spectrum - GC-MS (3 TMS)GC-MSsplash10-0w5l-2974000000-382a946b6e8fb2405c6e
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-0w5l-2974000000-382a946b6e8fb2405c6e
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00di-0900000000-70f5ce5df0fbc8549eee
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-0a59-9500000000-dcce9b8fbef9f60ac1be
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-01q9-9000000000-acc3e10ed8fce033ef29
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-00di-0900000000-4693e243c6ff991b1db9
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-00di-0900000000-ebabe051a2a75b2ef169
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0089-9400000000-c316b0398040a3e683e1
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-001i-9000000000-b51e69389ed95c714617
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-003r-9000000000-fecadf6fba072e864e73
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-1ff082847f737c786ce8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-008d-9400000000-33b7754bc017297ff2ce
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-008c-9300000000-19778449412743bcf27a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-4900000000-3cbdc72a15207691e1a3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-3900000000-0bb2806fe2867dce38c3
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9400000000-e1f4ab0fd240af6be33c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-4693e243c6ff991b1db9
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00di-0900000000-ebabe051a2a75b2ef169
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0089-9400000000-4318b1a531b3db6338bc
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-9000000000-b51e69389ed95c714617
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-003r-9000000000-fecadf6fba072e864e73
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as organic phosphonic acids. These are organic compounds containing phosphonic acid.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic phosphonic acids and derivatives
Sub Class
Organic phosphonic acids
Direct Parent
Organic phosphonic acids
Alternative Parents
Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organophosphorus compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Organophosphonic acid / Monocarboxylic acid or derivatives / Carboxylic acid / Carboxylic acid derivative / Organic oxygen compound / Organopnictogen compound / Organic oxide / Hydrocarbon derivative / Organophosphorus compound / Organooxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
monocarboxylic acid, phosphonic acids (CHEBI:15732)

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Not Available
Gene Name
phoA
Uniprot ID
P00634
Uniprot Name
Alkaline phosphatase
Molecular Weight
49438.17 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]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:24