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

ID: ALA8943

Chembl Id: CHEMBL8943

PubChem CID: 11143173

Max Phase: Preclinical

Molecular Formula: C20H22N2O5

Molecular Weight: 370.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(C[C@@H](Cc1cccc(O)c1)C(=O)N[C@H]1c2ccccc2C[C@H]1O)NO

Standard 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

Standard InChI Key:  VXDKQRWTOJFQKH-BJZITVGISA-N

Alternative Forms

1. Parent:

   

   ALA8943

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

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 370.40

Molecular Weight (Monoisotopic): 370.1529

AlogP: 1.22

#Rotatable Bonds: 6

Polar Surface Area: 118.89

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.79

CX Basic pKa: ┄

CX LogP: 1.22

CX LogD: 1.20

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.39

Np Likeness Score: 0.41

References

1. Yao W, Chao M, Wasserman ZR, Liu RQ, Covington MB, Newton R, Christ D, Wexler RR, Decicco CP..  (2002)  Potent P1' biphenylmethyl substituted aggrecanase inhibitors.,  12  (1): [PMID:11738583] [10.1016/s0960-894x(01)00704-1]

2. Yao W, Wasserman ZR, Chao M, Reddy G, Shi E, Liu RQ, Covington MB, Arner EC, Pratta MA, Tortorella M, Magolda RL, Newton R, Qian M, Ribadeneira MD, Christ D, Wexler RR, Decicco CP..  (2001)  Design and synthesis of a series of (2R)-N(4)-hydroxy-2-(3-hydroxybenzyl)-N(1)- [(1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]butanediamide derivatives as potent, selective, and orally bioavailable aggrecanase inhibitors.,  44  (21): [PMID:11585439] [10.1021/jm015533c]

3. Cuffaro D, Ciccone L, Rossello A, Nuti E, Santamaria S..  (2022)  Targeting Aggrecanases for Osteoarthritis Therapy: From Zinc Chelation to Exosite Inhibition.,  65  (20.0): [PMID:36250680] [10.1021/acs.jmedchem.2c01177]

Source

Source(1):

• Scientific Literature