NAV

(2S)-2-HYDROXY-2H-CHROMENE-2-CARBOXYLIC ACID

Identification

Generic Name
(2S)-2-HYDROXY-2H-CHROMENE-2-CARBOXYLIC ACID
DrugBank Accession Number
DB06952
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 192.1681
Monoisotopic: 192.042258744
Chemical Formula
C10H8O4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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
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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 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzopyrans
Sub Class
1-benzopyrans
Direct Parent
1-benzopyrans
Alternative Parents
Benzenoids / Alpha hydroxy acids and derivatives / Hemiacetals / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
1-benzopyran / Alpha-hydroxy acid / Aromatic heteropolycyclic compound / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hemiacetal / Hydrocarbon derivative / Hydroxy acid
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
LGYIZQLNYONEFJ-JTQLQIEISA-N
InChI
InChI=1S/C10H8O4/c11-9(12)10(13)6-5-7-3-1-2-4-8(7)14-10/h1-6,13H,(H,11,12)/t10-/m0/s1
IUPAC Name
(2S)-2-hydroxy-2H-chromene-2-carboxylic acid
SMILES
OC(=O)[C@@]1(O)OC2=CC=CC=C2C=C1

References

General References
Not Available
PubChem Compound
16122570
PubChem Substance
99443423
ChemSpider
17279488
PDBe Ligand
2C2
PDB Entries
2imd / 2ime

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 Solubility8.8 mg/mLALOGPS
logP0.92ALOGPS
logP1.83Chemaxon
logS-1.3ALOGPS
pKa (Strongest Acidic)2.85Chemaxon
pKa (Strongest Basic)-5.1Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area66.76 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity48.77 m3·mol-1Chemaxon
Polarizability18.05 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8004
Blood Brain Barrier+0.5602
Caco-2 permeable-0.6295
P-glycoprotein substrateSubstrate0.6155
P-glycoprotein inhibitor INon-inhibitor0.9567
P-glycoprotein inhibitor IINon-inhibitor0.9434
Renal organic cation transporterNon-inhibitor0.9273
CYP450 2C9 substrateNon-substrate0.771
CYP450 2D6 substrateNon-substrate0.9013
CYP450 3A4 substrateNon-substrate0.6395
CYP450 1A2 substrateNon-inhibitor0.6174
CYP450 2C9 inhibitorNon-inhibitor0.5828
CYP450 2D6 inhibitorNon-inhibitor0.9084
CYP450 2C19 inhibitorNon-inhibitor0.7335
CYP450 3A4 inhibitorNon-inhibitor0.6716
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8029
Ames testNon AMES toxic0.6479
CarcinogenicityNon-carcinogens0.958
BiodegradationNot ready biodegradable0.8633
Rat acute toxicity2.3095 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9895
hERG inhibition (predictor II)Non-inhibitor0.8694
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-MSsplash10-0gb9-1900000000-ab5cc07081bd040775b0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0900000000-5c2163201b94ad33e652
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0005-0900000000-e6df2f3816ad3106eb19
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0007-0900000000-1056b289157355417b43
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gbi-4900000000-b065d1f9d2b55542840a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-f52b4ad61d423fd7b7e5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014l-9500000000-289f235c4c86cbd92784
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]-136.66545
predicted
DeepCCS 1.0 (2019)
[M+H]+139.06102
predicted
DeepCCS 1.0 (2019)
[M+Na]+144.97356
predicted
DeepCCS 1.0 (2019)

Targets

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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 21:17 / Updated at June 12, 2020 16:52