(2s,3s)-Trans-2,3-Dihydro-3-Hydroxyanthranilic Acid

Identification

Generic Name
(2s,3s)-Trans-2,3-Dihydro-3-Hydroxyanthranilic Acid
DrugBank Accession Number
DB02124
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 155.1513
Monoisotopic: 155.058243159
Chemical Formula
C7H9NO3
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UTrans-2,3-dihydro-3-hydroxyanthranilate isomeraseNot AvailablePseudomonas fluorescens
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 secondary alcohols. These are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Alcohols and polyols
Direct Parent
Secondary alcohols
Alternative Parents
Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic homomonocyclic compound / Amine / Amino acid / Amino acid or derivatives / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic nitrogen compound
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
2,3-dihydro-3-hydroxyanthranilic acid (CHEBI:60844)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
XBTXTLKLSHACSS-WDSKDSINSA-N
InChI
InChI=1S/C7H9NO3/c8-6-4(7(10)11)2-1-3-5(6)9/h1-3,5-6,9H,8H2,(H,10,11)/t5-,6-/m0/s1
IUPAC Name
(5S,6S)-6-amino-5-hydroxycyclohexa-1,3-diene-1-carboxylic acid
SMILES
[H][C@]1(O)C=CC=C(C(O)=O)[C@]1([H])N

References

General References
Not Available
PubChem Compound
448825
PubChem Substance
46505773
ChemSpider
395510
ChEBI
60844
ChEMBL
CHEMBL1233316
ZINC
ZINC000005835424
PDBe Ligand
HHA
PDB Entries
1u1x / 1xua / 3cnm

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 Solubility65.4 mg/mLALOGPS
logP-2.4ALOGPS
logP-3.1Chemaxon
logS-0.38ALOGPS
pKa (Strongest Acidic)3.54Chemaxon
pKa (Strongest Basic)9.38Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area83.55 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity40.22 m3·mol-1Chemaxon
Polarizability14.61 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9072
Blood Brain Barrier-0.9812
Caco-2 permeable-0.6347
P-glycoprotein substrateNon-substrate0.7797
P-glycoprotein inhibitor INon-inhibitor0.94
P-glycoprotein inhibitor IINon-inhibitor0.9874
Renal organic cation transporterNon-inhibitor0.9421
CYP450 2C9 substrateNon-substrate0.8354
CYP450 2D6 substrateNon-substrate0.8597
CYP450 3A4 substrateNon-substrate0.7147
CYP450 1A2 substrateNon-inhibitor0.8078
CYP450 2C9 inhibitorNon-inhibitor0.9155
CYP450 2D6 inhibitorNon-inhibitor0.9418
CYP450 2C19 inhibitorNon-inhibitor0.8546
CYP450 3A4 inhibitorNon-inhibitor0.9369
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9139
Ames testNon AMES toxic0.9028
CarcinogenicityNon-carcinogens0.8862
BiodegradationReady biodegradable0.8215
Rat acute toxicity1.7977 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.952
hERG inhibition (predictor II)Non-inhibitor0.9627
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-MSsplash10-052s-9500000000-3907264e67cd3eb0e54f
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-24856c1d8eed8a5d83dd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9300000000-99b8d6419bab0a4949f7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03km-6900000000-adc42d1826274e6b7cb2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9200000000-0cdfea350ba36e94b1c7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9100000000-f7afb488844f1d5cbf3f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f8d-9000000000-087a4dfc0b44e44fb2c7
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]-132.5191838
predicted
DarkChem Lite v0.1.0
[M-H]-133.82928
predicted
DeepCCS 1.0 (2019)
[M+H]+133.4356838
predicted
DarkChem Lite v0.1.0
[M+H]+135.88742
predicted
DeepCCS 1.0 (2019)
[M+Na]+132.7700838
predicted
DarkChem Lite v0.1.0
[M+Na]+142.49986
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Pseudomonas fluorescens
Pharmacological action
Unknown
General Function
Isomerase activity
Specific Function
Isomerase that catalyzes the condensation of two molecules of trans-2,3-dihydro-3-hydroxyanthranilic acid (DHHA) into the phenazine ring system. The final product is not yet known.
Gene Name
phzF
Uniprot ID
Q51792
Uniprot Name
Trans-2,3-dihydro-3-hydroxyanthranilate isomerase
Molecular Weight
30052.965 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