5-[4-(1-Carboxymethyl-2-Oxo-Propylcarbamoyl)-Benzylsulfamoyl]-2-Hydroxy-Benzoic Acid

Identification

Name
5-[4-(1-Carboxymethyl-2-Oxo-Propylcarbamoyl)-Benzylsulfamoyl]-2-Hydroxy-Benzoic Acid
Accession Number
DB03124  (EXPT00045)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 464.446
Monoisotopic: 464.088950938
Chemical Formula
C20H20N2O9S
InChI Key
LBAHOXPDTNUYCX-INIZCTEOSA-N
InChI
InChI=1S/C20H20N2O9S/c1-11(23)16(9-18(25)26)22-19(27)13-4-2-12(3-5-13)10-21-32(30,31)14-6-7-17(24)15(8-14)20(28)29/h2-8,16,21,24H,9-10H2,1H3,(H,22,27)(H,25,26)(H,28,29)/t16-/m0/s1
IUPAC Name
5-{[(4-{[(2S)-1-carboxy-3-oxobutan-2-yl]carbamoyl}phenyl)methyl]sulfamoyl}-2-hydroxybenzoic acid
SMILES
[H][[email protected]@](CC(O)=O)(NC(=O)C1=CC=C(CNS(=O)(=O)C2=CC(C(O)=O)=C(O)C=C2)C=C1)C(C)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCaspase-3Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
5287429
PubChem Substance
46505887
ChemSpider
4449814
HET
161
PDB Entries
1nms

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.0278 mg/mLALOGPS
logP0.53ALOGPS
logP1.34ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)2.42ChemAxon
pKa (Strongest Basic)-0.96ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area187.17 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity111.1 m3·mol-1ChemAxon
Polarizability44.73 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9595
Blood Brain Barrier-0.7205
Caco-2 permeable-0.7025
P-glycoprotein substrateNon-substrate0.6256
P-glycoprotein inhibitor INon-inhibitor0.9218
P-glycoprotein inhibitor IINon-inhibitor0.8763
Renal organic cation transporterNon-inhibitor0.8952
CYP450 2C9 substrateSubstrate0.5713
CYP450 2D6 substrateNon-substrate0.8214
CYP450 3A4 substrateNon-substrate0.6224
CYP450 1A2 substrateNon-inhibitor0.8521
CYP450 2C9 inhibitorInhibitor0.5
CYP450 2D6 inhibitorNon-inhibitor0.8828
CYP450 2C19 inhibitorNon-inhibitor0.8019
CYP450 3A4 inhibitorNon-inhibitor0.9318
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7291
Ames testNon AMES toxic0.7561
CarcinogenicityNon-carcinogens0.6379
BiodegradationNot ready biodegradable0.9363
Rat acute toxicity2.1228 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9741
hERG inhibition (predictor II)Non-inhibitor0.9104
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Beta amino acids and derivatives
Alternative Parents
Benzenesulfonamides / Salicylic acids / Benzamides / Benzenesulfonyl compounds / Benzoic acids / Benzoyl derivatives / Gamma-keto acids and derivatives / 1-hydroxy-2-unsubstituted benzenoids / Dicarboxylic acids and derivatives / Organosulfonamides
show 9 more
Substituents
Beta amino acid or derivatives / Hydroxybenzoic acid / Benzenesulfonamide / Salicylic acid or derivatives / Salicylic acid / Benzamide / Benzoic acid or derivatives / Benzenesulfonyl group / Benzoic acid / Gamma-keto acid
show 27 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Phospholipase a2 activator activity
Specific Function
Involved in the activation cascade of caspases responsible for apoptosis execution. At the onset of apoptosis it proteolytically cleaves poly(ADP-ribose) polymerase (PARP) at a '216-Asp-|-Gly-217' ...
Gene Name
CASP3
Uniprot ID
P42574
Uniprot Name
Caspase-3
Molecular Weight
31607.58 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. [PubMed:17139284]
  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. [PubMed:17016423]
  3. 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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:08