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

ID: ALA98388

Chembl Id: CHEMBL98388

PubChem CID: 44330234

Max Phase: Preclinical

Molecular Formula: C20H20FNO4

Molecular Weight: 357.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)c1ccc2c(c1)[C@H](NC(=O)c1ccc(F)cc1)[C@H](O)C(C)(C)O2

Standard InChI:  InChI=1S/C20H20FNO4/c1-11(23)13-6-9-16-15(10-13)17(18(24)20(2,3)26-16)22-19(25)12-4-7-14(21)8-5-12/h4-10,17-18,24H,1-3H3,(H,22,25)/t17-,18-/m0/s1

Standard InChI Key:  RCLXAPJEFHPYEG-ROUUACIJSA-N

Alternative Forms

1. Parent:

   

   ALA98388

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

Molecule Features

Natural Product: Yes

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: 357.38

Molecular Weight (Monoisotopic): 357.1376

AlogP: 3.03

#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: 12.70

CX Basic pKa: ┄

CX LogP: 2.27

CX LogD: 2.27

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.83

Np Likeness Score: 0.16

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