N-((3R,4S)-6-Acetyl-3-hydroxy-2,2-dimethyl-chroman-4-yl)-2,6-dichloro-benzamide

ID: ALA95250

Chembl Id: CHEMBL95250

PubChem CID: 21309471

Max Phase: Preclinical

Molecular Formula: C20H19Cl2NO4

Molecular Weight: 408.28

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1ccc2c(c1)[C@H](NC(=O)c1c(Cl)cccc1Cl)[C@@H](O)C(C)(C)O2

Standard InChI:  InChI=1S/C20H19Cl2NO4/c1-10(24)11-7-8-15-12(9-11)17(18(25)20(2,3)27-15)23-19(26)16-13(21)5-4-6-14(16)22/h4-9,17-18,25H,1-3H3,(H,23,26)/t17-,18+/m0/s1

Standard InChI Key:  YSYJGFABOFVTIV-ZWKOTPCHSA-N

Alternative Forms

1. Parent:

   

   ALA95250

   N-[(3R,4S)-6-acetyl-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-2,6-dichlorobenzamide

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: 408.28

Molecular Weight (Monoisotopic): 407.0691

AlogP: 4.20

#Rotatable Bonds: 3

Polar Surface Area: 75.63

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.42

CX Basic pKa: ┄

CX LogP: 3.34

CX LogD: 3.34

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.75

Np Likeness Score: 0.20

References

1. Chan WN, Evans JM, Hadley MS, Herdon HJ, Jerman JC, Parsons AA, Read SJ, Stean TO, Thompson M, Upton N..  (1999)  Identification of (-)-cis-6-acetyl-4S-(3-chloro-4-fluoro-benzoylamino)- 3,4-dihydro-2,2-dimethyl-2H-benzo[b]pyran-3S-ol as a potential antimigraine agent.,  9  (2): [PMID:10021946] [10.1016/s0960-894x(98)00728-8]

Source

Source(1):

• Scientific Literature