(2R)-N~4~-hydroxy-2-(3-hydroxybenzyl)-N~1~-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]butanediamide

Identification

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Name
(2R)-N~4~-hydroxy-2-(3-hydroxybenzyl)-N~1~-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]butanediamide
Accession Number
DB06837
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: 370.3991
Monoisotopic: 370.152871824
Chemical Formula
C20H22N2O5
InChI Key
VXDKQRWTOJFQKH-BJZITVGISA-N
InChI
InChI=1S/C20H22N2O5/c23-15-6-3-4-12(9-15)8-14(11-18(25)22-27)20(26)21-19-16-7-2-1-5-13(16)10-17(19)24/h1-7,9,14,17,19,23-24,27H,8,10-11H2,(H,21,26)(H,22,25)/t14-,17-,19+/m1/s1
IUPAC Name
(2R)-N'-hydroxy-N-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-2-[(3-hydroxyphenyl)methyl]butanediamide
SMILES
[H][C@](CC(=O)NO)(CC1=CC(O)=CC=C1)C(=O)N[C@@]1([H])C2=C(C[C@@]1([H])O)C=CC=C2

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UA disintegrin and metalloproteinase with thrombospondin motifs 5Not AvailableHumans
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
11143173
PubChem Substance
99443308
ChemSpider
9318285
BindingDB
50104965
ChEMBL
CHEMBL8943
HET
099
PDB Entries
3hyg

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 Solubility0.162 mg/mLALOGPS
logP0.7ALOGPS
logP1.22ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)8.79ChemAxon
pKa (Strongest Basic)-0.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area118.89 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity98.65 m3·mol-1ChemAxon
Polarizability38.08 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9536
Blood Brain Barrier+0.715
Caco-2 permeable-0.7405
P-glycoprotein substrateNon-substrate0.5678
P-glycoprotein inhibitor INon-inhibitor0.913
P-glycoprotein inhibitor IINon-inhibitor0.9797
Renal organic cation transporterNon-inhibitor0.9441
CYP450 2C9 substrateNon-substrate0.7678
CYP450 2D6 substrateNon-substrate0.8302
CYP450 3A4 substrateSubstrate0.5502
CYP450 1A2 substrateNon-inhibitor0.6807
CYP450 2C9 inhibitorNon-inhibitor0.8171
CYP450 2D6 inhibitorNon-inhibitor0.8849
CYP450 2C19 inhibitorNon-inhibitor0.7033
CYP450 3A4 inhibitorNon-inhibitor0.8353
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7328
Ames testAMES toxic0.6418
CarcinogenicityNon-carcinogens0.8439
BiodegradationNot ready biodegradable0.9082
Rat acute toxicity2.4098 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9838
hERG inhibition (predictor II)Non-inhibitor0.7662
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 indanes. These are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Indanes
Sub Class
Not Available
Direct Parent
Indanes
Alternative Parents
1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / N-acyl amines / Benzene and substituted derivatives / Secondary carboxylic acid amides / Secondary alcohols / Hydroxamic acids / Organopnictogen compounds / Organonitrogen compounds / Organic oxides
show 2 more
Substituents
Indane / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Phenol / Monocyclic benzene moiety / Fatty amide / Fatty acyl / N-acyl-amine / Carboxamide group / Hydroxamic acid
show 13 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Cleaves aggrecan, a cartilage proteoglycan, and may be involved in its turnover. May play an important role in the destruction of aggrecan in arthritic diseases. May play a role in proteolytic proc...
Gene Name
ADAMTS5
Uniprot ID
Q9UNA0
Uniprot Name
A disintegrin and metalloproteinase with thrombospondin motifs 5
Molecular Weight
101716.955 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. [PubMed:10592235]

Drug created on September 15, 2010 15:17 / Updated on June 04, 2019 06:30