Carabryl 3-Phenylacrylate

ID: ALA2229158

PubChem CID: 76307897

Max Phase: Preclinical

Molecular Formula: C24H28O4

Molecular Weight: 380.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@@H]2C[C@]3(C)C(CCC(C)OC(=O)/C=C/c4ccccc4)[C@@H]3C[C@H]12

Standard InChI:  InChI=1S/C24H28O4/c1-15(27-22(25)12-10-17-7-5-4-6-8-17)9-11-19-20-13-18-16(2)23(26)28-21(18)14-24(19,20)3/h4-8,10,12,15,18-21H,2,9,11,13-14H2,1,3H3/b12-10+/t15?,18-,19?,20+,21-,24-/m1/s1

Standard InChI Key:  LKVBGZPNRWSRIP-HCHYEGHLSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   29.1789  -29.6127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1789  -27.9626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8909  -28.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8953  -29.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6781  -29.4503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1573  -28.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6707  -28.1212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4668  -29.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4668  -28.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7524  -28.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9273  -28.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5148  -28.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6898  -28.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2773  -27.3629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2773  -28.7918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.0502  -27.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9372  -30.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.9823  -28.7786    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4524  -28.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0399  -29.5064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0399  -28.0773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2157  -29.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8033  -30.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9803  -30.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5680  -30.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9798  -31.6448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8083  -31.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2169  -30.9291    0.0000 C   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 27  1  0
 27 28  2  0
 28 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2229158

   CARABRYL 3-PHENYLACRYLATE

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: 380.48

Molecular Weight (Monoisotopic): 380.1988

AlogP: 4.56

#Rotatable Bonds: 6

Polar Surface Area: 52.60

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.27

CX LogD: 5.27

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: 2.32

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