NAV

2-Hydroxybenzalpyruvate

Identification

Generic Name
2-Hydroxybenzalpyruvate
DrugBank Accession Number
DB08636
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 192.1681
Monoisotopic: 192.042258744
Chemical Formula
C10H8O4
Synonyms
  • (3E)-4-(2-Hydroxyphenyl)-2-oxobut-3-enoate
  • (3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoic acid
  • 4-(2-Hydroxyphenyl)-2-oxo-3-butenoic acid
  • ortho-Hydroxybenzalpyruvate
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U2-hydroxychromene-2-carboxylate isomeraseNot AvailablePseudomonas putida
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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as hydroxycinnamic acids and derivatives. These are compounds containing an cinnamic acid (or a derivative thereof) where the benzene ring is hydroxylated.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Cinnamic acids and derivatives
Sub Class
Hydroxycinnamic acids and derivatives
Direct Parent
Hydroxycinnamic acids and derivatives
Alternative Parents
Styrenes / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Alpha-keto acids and derivatives / Enones / Alpha-hydroxy ketones / Acryloyl compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides
show 1 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Acryloyl-group / Alpha,beta-unsaturated ketone / Alpha-hydroxy ketone / Alpha-keto acid / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxylic acid
show 13 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
2-oxo monocarboxylic acid (CHEBI:59354)
Affected organisms
Not Available

Chemical Identifiers

UNII
8WGN3TR2PL
CAS number
90293-62-2
InChI Key
HMXOGGUFCBUALL-AATRIKPKSA-N
InChI
InChI=1S/C10H8O4/c11-8-4-2-1-3-7(8)5-6-9(12)10(13)14/h1-6,11H,(H,13,14)/b6-5+
IUPAC Name
(3E)-4-(2-hydroxyphenyl)-2-oxobut-3-enoic acid
SMILES
OC(=O)C(=O)\C=C\C1=CC=CC=C1O

References

General References
Not Available
KEGG Compound
C06203
PubChem Compound
5280911
PubChem Substance
99445107
ChemSpider
4444428
ChEBI
59354
PDBe Ligand
TOH

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 Solubility0.623 mg/mLALOGPS
logP1.86ALOGPS
logP2.12Chemaxon
logS-2.5ALOGPS
pKa (Strongest Acidic)2.84Chemaxon
pKa (Strongest Basic)-6.4Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area74.6 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity50.39 m3·mol-1Chemaxon
Polarizability18.3 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9508
Blood Brain Barrier+0.6423
Caco-2 permeable+0.5212
P-glycoprotein substrateNon-substrate0.677
P-glycoprotein inhibitor INon-inhibitor0.948
P-glycoprotein inhibitor IINon-inhibitor0.9734
Renal organic cation transporterNon-inhibitor0.9302
CYP450 2C9 substrateNon-substrate0.7986
CYP450 2D6 substrateNon-substrate0.9157
CYP450 3A4 substrateNon-substrate0.7191
CYP450 1A2 substrateNon-inhibitor0.9509
CYP450 2C9 inhibitorNon-inhibitor0.7709
CYP450 2D6 inhibitorNon-inhibitor0.9192
CYP450 2C19 inhibitorNon-inhibitor0.8728
CYP450 3A4 inhibitorNon-inhibitor0.935
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9354
Ames testNon AMES toxic0.96
CarcinogenicityNon-carcinogens0.8992
BiodegradationReady biodegradable0.7722
Rat acute toxicity1.5021 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9738
hERG inhibition (predictor II)Non-inhibitor0.9683
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-MSsplash10-00kb-2900000000-4f71b197b19a3d594131
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00r7-0900000000-bfb7878efe7452567ff1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kb-0900000000-4d18b5beb5865f3ce4af
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f96-3900000000-44058d87aa33fb01f84a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0uyi-0900000000-b587496211e98914d37b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-9500000000-b4b36347df23cfe8ea43
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udr-9700000000-14570e140d10ea53f4ca
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]-140.21626
predicted
DeepCCS 1.0 (2019)
[M+H]+142.61182
predicted
DeepCCS 1.0 (2019)
[M+Na]+148.78725
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. 2-hydroxychromene-2-carboxylate isomerase
Kind
Protein
Organism
Pseudomonas putida
Pharmacological action
Unknown
General Function
Protein disulfide oxidoreductase activity
Specific Function
Involved in the naphthalene catabolic pathway. Catalyzes the reversible glutathione-dependent isomerization of 2-hydroxychromene-2-carboxylate (HCCA) to trans-O-hydroxybenzylidenepyruvate (THBPA).
Gene Name
nahD
Uniprot ID
Q51948
Uniprot Name
2-hydroxychromene-2-carboxylate isomerase
Molecular Weight
23061.0 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:33 / Updated at December 11, 2021 01:26