Carabryl 4-Cyanobenzoate

ID: ALA2229147

PubChem CID: 57343578

Max Phase: Preclinical

Molecular Formula: C23H25NO4

Molecular Weight: 379.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@@H]2C[C@]3(C)C(CCC(C)OC(=O)c4ccc(C#N)cc4)[C@@H]3C[C@H]12

Standard InChI:  InChI=1S/C23H25NO4/c1-13(27-22(26)16-7-5-15(12-24)6-8-16)4-9-18-19-10-17-14(2)21(25)28-20(17)11-23(18,19)3/h5-8,13,17-20H,2,4,9-11H2,1,3H3/t13?,17-,18?,19+,20-,23-/m1/s1

Standard InChI Key:  OJIBJWGRLULSGL-SEEHDLRDSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   27.6705  -17.1584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6705  -15.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3825  -15.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3871  -16.7465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1697  -16.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6489  -16.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1624  -15.6671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9585  -16.7501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9585  -15.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2441  -16.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4191  -16.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0065  -15.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1815  -15.6232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7690  -14.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7690  -16.3376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5418  -15.2084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4289  -17.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4739  -16.3243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9440  -16.3376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5315  -17.0521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5315  -15.6232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7074  -17.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2950  -17.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7075  -18.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5368  -18.4736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9455  -17.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2971  -19.1972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8856  -19.9122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  9  2  1  0
  8  1  1  1
  4  1  1  1
  3  2  1  1
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  3  1  0
  9  8  1  0
 10  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
  9 16  1  6
  5 17  2  0
  6 18  2  0
 15 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 20  1  0
 27 28  3  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2229147

   CARABRYL 4-CYANOBENZOATE

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: 379.46

Molecular Weight (Monoisotopic): 379.1784

AlogP: 4.03

#Rotatable Bonds: 5

Polar Surface Area: 76.39

Molecular Species: ┄

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.59

CX LogD: 4.59

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.57

Np Likeness Score: 1.69

References

1. Feng JT, Wang H, Ren SX, He J, Liu Y, Zhang X..  (2012)  Synthesis and antifungal activities of carabrol ester derivatives.,  60  (15): [PMID:22443262] [10.1021/jf205123d]

Source

Source(1):

• Scientific Literature