Carabryl alpha-Naphthylcarboxylate

ID: ALA2229161

PubChem CID: 76311477

Max Phase: Preclinical

Molecular Formula: C26H28O4

Molecular Weight: 404.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@@H]2C[C@]3(C)C(CCC(C)OC(=O)c4cccc5ccccc45)[C@@H]3C[C@H]12

Standard InChI:  InChI=1S/C26H28O4/c1-15(29-25(28)19-10-6-8-17-7-4-5-9-18(17)19)11-12-21-22-13-20-16(2)24(27)30-23(20)14-26(21,22)3/h4-10,15,20-23H,2,11-14H2,1,3H3/t15?,20-,21?,22+,23-,26-/m1/s1

Standard InChI Key:  HLPXOCLCSAPGPO-MTRMBMJNSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
   19.9004   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9004   -1.5095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6132   -1.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6177   -2.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4007   -2.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8818   -2.3301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3935   -1.6673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1876   -2.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1876   -1.9283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4724   -2.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6471   -2.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2366   -1.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4114   -1.6236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9967   -0.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9967   -2.3389    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7730   -1.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6587   -3.7820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7071   -2.3256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1715   -2.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7609   -3.0541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7609   -1.6236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9365   -3.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5220   -3.7635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9367   -4.4797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1729   -3.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7649   -4.4760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1753   -5.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9979   -5.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4083   -4.4655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9913   -3.7580    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 26  1  0
 25 20  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2229161

   CARABRYL ALPHA-NAPHTHYLCARBOXYLATE

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: 404.51

Molecular Weight (Monoisotopic): 404.1988

AlogP: 5.31

#Rotatable Bonds: 5

Polar Surface Area: 52.60

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.73

CX LogD: 5.73

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: 1.72

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