Carabryl 4-Bromophenylacetate

ID: ALA2229155

PubChem CID: 76307896

Max Phase: Preclinical

Molecular Formula: C23H27BrO4

Molecular Weight: 447.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@@H]2C[C@]3(C)C(CCC(C)OC(=O)Cc4ccc(Br)cc4)[C@@H]3C[C@H]12

Standard InChI:  InChI=1S/C23H27BrO4/c1-13(27-21(25)10-15-5-7-16(24)8-6-15)4-9-18-19-11-17-14(2)22(26)28-20(17)12-23(18,19)3/h5-8,13,17-20H,2,4,9-12H2,1,3H3/t13?,17-,18?,19+,20-,23-/m1/s1

Standard InChI Key:  WLEWTPXNBXEKPB-SEEHDLRDSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
   29.0252  -25.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0252  -23.9047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7373  -24.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7417  -25.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5244  -25.3924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0037  -24.7252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5171  -24.0633    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3132  -25.1464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3132  -24.3214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5987  -24.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7737  -24.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3611  -24.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5361  -24.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1236  -23.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1236  -24.7339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8965  -23.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7836  -26.1757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8286  -24.7207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2986  -24.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8861  -25.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8861  -24.0194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.0619  -25.4434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6558  -24.7264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8324  -24.7212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4152  -25.4329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8273  -26.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6493  -26.1533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5902  -25.4290    0.0000 Br  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  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2229155

   CARABRYL 4-BROMOPHENYLACETATE

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: 447.37

Molecular Weight (Monoisotopic): 446.1093

AlogP: 4.85

#Rotatable Bonds: 6

Polar Surface Area: 52.60

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.29

CX LogD: 5.29

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.46

Np Likeness Score: 1.91

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