(2R)-N~4~-hydroxy-2-(3-hydroxybenzyl)-N~1~-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]butanediamide
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Identification
- Generic Name
- (2R)-N~4~-hydroxy-2-(3-hydroxybenzyl)-N~1~-[(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]butanediamide
- DrugBank Accession Number
- DB06837
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 370.3991
Monoisotopic: 370.152871824 - Chemical Formula
- C20H22N2O5
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UA disintegrin and metalloproteinase with thrombospondin motifs 5 Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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 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
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Aromatic homopolycyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Fatty acyl / Fatty amide / Hydrocarbon derivative show 13 more
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- 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
References
- General References
- Not Available
- External Links
- PubChem Compound
- 11143173
- PubChem Substance
- 99443308
- ChemSpider
- 9318285
- BindingDB
- 50104965
- ChEMBL
- CHEMBL8943
- ZINC
- ZINC000013436282
- PDBe Ligand
- 099
- PDB Entries
- 3hyg
Clinical Trials
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
Property Value Source Water Solubility 0.162 mg/mL ALOGPS logP 0.7 ALOGPS logP 1.22 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 8.79 Chemaxon pKa (Strongest Basic) -1.4 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 118.89 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 98.65 m3·mol-1 Chemaxon Polarizability 38.08 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9536 Blood Brain Barrier + 0.715 Caco-2 permeable - 0.7405 P-glycoprotein substrate Non-substrate 0.5678 P-glycoprotein inhibitor I Non-inhibitor 0.913 P-glycoprotein inhibitor II Non-inhibitor 0.9797 Renal organic cation transporter Non-inhibitor 0.9441 CYP450 2C9 substrate Non-substrate 0.7678 CYP450 2D6 substrate Non-substrate 0.8302 CYP450 3A4 substrate Substrate 0.5502 CYP450 1A2 substrate Non-inhibitor 0.6807 CYP450 2C9 inhibitor Non-inhibitor 0.8171 CYP450 2D6 inhibitor Non-inhibitor 0.8849 CYP450 2C19 inhibitor Non-inhibitor 0.7033 CYP450 3A4 inhibitor Non-inhibitor 0.8353 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7328 Ames test AMES toxic 0.6418 Carcinogenicity Non-carcinogens 0.8439 Biodegradation Not ready biodegradable 0.9082 Rat acute toxicity 2.4098 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9838 hERG inhibition (predictor II) Non-inhibitor 0.7662
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-00li-1139000000-8735aec1300b864da1b1 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-0109000000-4cc9498c30f951e8d3ee Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-006x-0947000000-06f72aa84f43097bedb6 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-029l-2918000000-19f7ebcc0eed644b95dc Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-05vn-2900000000-4181e9719daf43dbe153 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-01xc-0921000000-35bdc2967c63b4a3617a Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 178.57947 predictedDeepCCS 1.0 (2019) [M+H]+ 180.97504 predictedDeepCCS 1.0 (2019) [M+Na]+ 186.92612 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- 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