NAV

2-(Phosphonooxy)Butanoic Acid

Identification

Generic Name
2-(Phosphonooxy)Butanoic Acid
DrugBank Accession Number
DB03248
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 184.0844
Monoisotopic: 184.013674532
Chemical Formula
C4H9O6P
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
U2-dehydro-3-deoxyphosphooctonate aldolaseNot AvailableAquifex aeolicus (strain VF5)
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 monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Organic phosphoric acids and derivatives
Sub Class
Phosphate esters
Direct Parent
Monoalkyl phosphates
Alternative Parents
Fatty acids and conjugates / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Fatty acid / Hydrocarbon derivative / Monoalkyl phosphate / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
OETAGSCBSKODFW-GSVOUGTGSA-N
InChI
InChI=1S/C4H9O6P/c1-2-3(4(5)6)10-11(7,8)9/h3H,2H2,1H3,(H,5,6)(H2,7,8,9)/t3-/m1/s1
IUPAC Name
(2R)-2-(phosphonooxy)butanoic acid
SMILES
CC[C@@H](OP(O)(O)=O)C(O)=O

References

General References
Not Available
PubChem Compound
17754119
PubChem Substance
46509185
ChemSpider
16744149
ZINC
ZINC000012503329
PDBe Ligand
PEZ
PDB Entries
1pck

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 Solubility22.1 mg/mLALOGPS
logP-1.4ALOGPS
logP-0.073Chemaxon
logS-0.92ALOGPS
pKa (Strongest Acidic)1.14Chemaxon
Physiological Charge-3Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area104.06 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity34.24 m3·mol-1Chemaxon
Polarizability14.38 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.7857
Blood Brain Barrier+0.9386
Caco-2 permeable-0.7536
P-glycoprotein substrateNon-substrate0.6874
P-glycoprotein inhibitor INon-inhibitor0.8896
P-glycoprotein inhibitor IINon-inhibitor0.9553
Renal organic cation transporterNon-inhibitor0.958
CYP450 2C9 substrateNon-substrate0.7807
CYP450 2D6 substrateNon-substrate0.8561
CYP450 3A4 substrateNon-substrate0.6403
CYP450 1A2 substrateNon-inhibitor0.9183
CYP450 2C9 inhibitorNon-inhibitor0.8795
CYP450 2D6 inhibitorNon-inhibitor0.9163
CYP450 2C19 inhibitorNon-inhibitor0.874
CYP450 3A4 inhibitorNon-inhibitor0.9629
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9735
Ames testNon AMES toxic0.8051
CarcinogenicityNon-carcinogens0.5641
BiodegradationNot ready biodegradable0.5872
Rat acute toxicity2.2219 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9691
hERG inhibition (predictor II)Non-inhibitor0.9027
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-MSsplash10-0002-9100000000-9a240e22ca35ad6f2bc5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-5900000000-e8b23837aeb45e6bd5f9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-d7a2d8f56e1910f2a746
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0005-9000000000-f5ea7d66f0158a2f0796
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-ea07a0e285fd945e21bb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-6db2c4fa0bbdd4ad9db4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-42e43f7148e4d33025c9
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]-124.74115
predicted
DeepCCS 1.0 (2019)
[M+H]+128.10931
predicted
DeepCCS 1.0 (2019)
[M+Na]+137.35265
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 2-dehydro-3-deoxyphosphooctonate aldolase
Kind
Protein
Organism
Aquifex aeolicus (strain VF5)
Pharmacological action
Unknown
General Function
3-deoxy-8-phosphooctulonate synthase activity
Specific Function
Not Available
Gene Name
kdsA
Uniprot ID
O66496
Uniprot Name
2-dehydro-3-deoxyphosphooctonate aldolase
Molecular Weight
29734.17 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. [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