NAV

2-[(1R)-1-CARBOXY-2-(4-HYDROXYPHENYL)ETHYL]-1,3-DIOXOISOINDOLINE-5-CARBOXYLIC ACID

Identification

Generic Name
2-[(1R)-1-CARBOXY-2-(4-HYDROXYPHENYL)ETHYL]-1,3-DIOXOISOINDOLINE-5-CARBOXYLIC ACID
DrugBank Accession Number
DB07663
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 355.2983
Monoisotopic: 355.069201775
Chemical Formula
C18H13NO7
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBeta-lactamaseNot 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

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 tyrosine and derivatives. These are compounds containing tyrosine or a derivative thereof resulting from reaction of tyrosine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Tyrosine and derivatives
Alternative Parents
Phenylalanine and derivatives / Phthalimides / Phenylpropanoic acids / Amphetamines and derivatives / Isoindoles / 1-hydroxy-2-unsubstituted benzenoids / N-substituted carboxylic acid imides / Dicarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds
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Substituents
1-hydroxy-2-unsubstituted benzenoid / 3-phenylpropanoic-acid / Amphetamine or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid imide / Carboxylic acid imide, n-substituted
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
QISJEFYTLZTWIQ-CQSZACIVSA-N
InChI
InChI=1S/C18H13NO7/c20-11-4-1-9(2-5-11)7-14(18(25)26)19-15(21)12-6-3-10(17(23)24)8-13(12)16(19)22/h1-6,8,14,20H,7H2,(H,23,24)(H,25,26)/t14-/m1/s1
IUPAC Name
2-[(1R)-1-carboxy-2-(4-hydroxyphenyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carboxylic acid
SMILES
[H][C@](CC1=CC=C(O)C=C1)(N1C(=O)C2=C(C=C(C=C2)C(O)=O)C1=O)C(O)=O

References

General References
Not Available
PubChem Compound
7013169
PubChem Substance
99444134
ChemSpider
5376302
ChEMBL
CHEMBL264702
PDBe Ligand
DK2
PDB Entries
2pu2

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 Solubility0.0521 mg/mLALOGPS
logP1.58ALOGPS
logP1.97Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)2.79Chemaxon
pKa (Strongest Basic)-6Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area132.21 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity88.65 m3·mol-1Chemaxon
Polarizability34.32 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9738
Blood Brain Barrier+0.9243
Caco-2 permeable-0.6029
P-glycoprotein substrateNon-substrate0.6508
P-glycoprotein inhibitor INon-inhibitor0.9767
P-glycoprotein inhibitor IINon-inhibitor0.8487
Renal organic cation transporterNon-inhibitor0.8066
CYP450 2C9 substrateNon-substrate0.7609
CYP450 2D6 substrateNon-substrate0.8164
CYP450 3A4 substrateNon-substrate0.5468
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9313
CYP450 2D6 inhibitorNon-inhibitor0.543
CYP450 2C19 inhibitorNon-inhibitor0.93
CYP450 3A4 inhibitorNon-inhibitor0.9482
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8681
Ames testNon AMES toxic0.8296
CarcinogenicityNon-carcinogens0.9324
BiodegradationReady biodegradable0.5194
Rat acute toxicity2.4263 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9801
hERG inhibition (predictor II)Non-inhibitor0.9294
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-MSsplash10-090a-1947000000-e0d2f88dd9d2b7263c15
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bti-0309000000-9c3ef4f30122f2997d4d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0902000000-745d821f68a6fbd100b4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gvo-0869000000-58b7c0087e87ed8525ea
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-0932000000-b3ee52929dee15384001
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kg-1920000000-6032e5ea78a61f3b6767
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0aos-1911000000-60fae8c824f1a2e649aa
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]-184.7242
predicted
DeepCCS 1.0 (2019)
[M+H]+187.08217
predicted
DeepCCS 1.0 (2019)
[M+Na]+193.60887
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Beta-lactamase
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Beta-lactamase activity
Specific Function
This protein is a serine beta-lactamase with a substrate specificity for cephalosporins.
Gene Name
ampC
Uniprot ID
P00811
Uniprot Name
Beta-lactamase
Molecular Weight
41555.3 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 21:24 / Updated at June 12, 2020 16:52