ID: ALA39933

Max Phase: Phase

Molecular Formula: C20H20FNO4

Molecular Weight: 357.38

Molecule Type: Small molecule

Representations

Synonyms (2): Carabersat | SB-204269-EO
Synonyms from Alternative Forms(2):

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-ZWKOTPCHSA-N

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: Yes

Availability: No

Prodrug: No

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: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

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, Morgan HK, Thompson M, Upton N.  (1997)  Conformational preference of the 6-acetyl group in novel anticonvulsant trans 4S-benzamido-benzo[b]pyran-3R-ols,  7  (12): [10.1016/S0960-894X(97)00264-3]

2. Austin NE, Hadley MS, Harling JD, Harrington FP, Macdonald GJ, Mitchell DJ, Riley GJ, Stean TO, Stemp G, Stratton SC, Thompson M, Upton N..  (2003)  The design of 8,8-dimethyl[1,6]naphthyridines as potential anticonvulsant agents.,  13  (10): [PMID:12729628] [10.1016/s0960-894x(03)00288-9]

3. 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]

4. Chan WN, Hadley MS, Harling JD, Herdon HJ, Jerman JC, Orlek BS, Stean TO, Thompson M, Upton N, Ward RW..  (1998)  Identification of a series of 1,2,3,4-tetrahydroisoquinolinyl-benzamides with potential anticonvulsant activity.,  8  (20): [PMID:9873645] [10.1016/s0960-894x(98)00523-x]

5. Chan WN, Evans JM, Hadley MS, Herdon HJ, Jerman JC, Morgan HK, Stean TO, Thompson M, Upton N, Vong AK..  (1996)  Synthesis of novel trans-4-(substituted-benzamido)-3,4-dihydro-2H-benzo[b]-pyran-3-ol derivatives as potential anticonvulsant agents with a distinctive binding profile.,  39  (23): [PMID:8917640] [10.1021/jm960535w]

6. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

7. PubChem BioAssay data set, 

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names