N-((3R,4S)-6-Acetyl-3-hydroxy-2,2-dimethyl-chroman-4-yl)-2,3,5-trichloro-benzamide

ID: ALA99341

Chembl Id: CHEMBL99341

PubChem CID: 44330148

Max Phase: Preclinical

Molecular Formula: C20H18Cl3NO4

Molecular Weight: 442.73

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1ccc2c(c1)[C@H](NC(=O)c1cc(Cl)cc(Cl)c1Cl)[C@@H](O)C(C)(C)O2

Standard InChI:  InChI=1S/C20H18Cl3NO4/c1-9(25)10-4-5-15-12(6-10)17(18(26)20(2,3)28-15)24-19(27)13-7-11(21)8-14(22)16(13)23/h4-8,17-18,26H,1-3H3,(H,24,27)/t17-,18+/m0/s1

Standard InChI Key:  HWEIFQGXMQNOJP-ZWKOTPCHSA-N

Alternative Forms

1. Parent:

   

   ALA99341

   N-[(3R,4S)-6-acetyl-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-2,3,5-trichlorobenzamide

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: 442.73

Molecular Weight (Monoisotopic): 441.0301

AlogP: 4.85

#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: 11.32

CX Basic pKa: ┄

CX LogP: 3.94

CX LogD: 3.94

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.53

Np Likeness Score: 0.07

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