ID: ALA16515

Max Phase: Preclinical

Molecular Formula: C19H17FN2O3

Molecular Weight: 340.35

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC1(C)Oc2ccc(C#N)cc2[C@H](NC(=O)c2ccc(F)cc2)[C@H]1O

Standard InChI:  InChI=1S/C19H17FN2O3/c1-19(2)17(23)16(14-9-11(10-21)3-8-15(14)25-19)22-18(24)12-4-6-13(20)7-5-12/h3-9,16-17,23H,1-2H3,(H,22,24)/t16-,17+/m0/s1

Standard InChI Key:  YCQGEJDEIFFVDC-DLBZAZTESA-N

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

Properties

Molecular Weight: 340.35

Molecular Weight (Monoisotopic): 340.1223

AlogP: 2.70

#Rotatable Bonds: 2

Polar Surface Area: 82.35

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.48

CX Basic pKa:

CX LogP: 2.57

CX LogD: 2.57

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.88

Np Likeness Score: -0.27

References

1. Blackburn TP, Buckingham RE, Chan WN, Evans JM, Hadley MS, Thompson M, Upton N, Stean TO, Stemp G, Vong AK.  (1995)  Stereochemical differentiation of anticonvulsant and antihypertensive effects in 4-(fluorobenzoylamino)-benzopyrans,  5  (11): [10.1016/0960-894X(95)00180-2]

2. Brown TH, Campbell CA, Chan WN, Evans JM, Martin RT, Stean TO, Stemp G, Stevens NC, Thompson M, Upton N, Vong AK.  (1995)  Stereochemical preferences and requirement for the 3-hydroxyl group in novel anticonvulsant 4-fluorobenzoylamino benzopyrans,  5  (21): [10.1016/0960-894X(95)00437-X]

3. 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]

Source

Source(1):

• Scientific Literature