(E)-N-(3-bromophenyl)-3-methyl-5-((1R,4aR,8aR)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)pent-2-enamide

ID: ALA4099730

PubChem CID: 137660030

Max Phase: Preclinical

Molecular Formula: C26H36BrNO

Molecular Weight: 458.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@@H]2C(C)(C)CCC[C@@]2(C)[C@@H]1CC/C(C)=C/C(=O)Nc1cccc(Br)c1

Standard InChI:  InChI=1S/C26H36BrNO/c1-18(16-24(29)28-21-9-6-8-20(27)17-21)10-12-22-19(2)11-13-23-25(3,4)14-7-15-26(22,23)5/h6,8-9,16-17,22-23H,2,7,10-15H2,1,3-5H3,(H,28,29)/b18-16+/t22-,23-,26+/m1/s1

Standard InChI Key:  BRWHOQSLBMONPJ-WKGMFPAASA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
   10.7143  -31.3133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3635  -30.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9545  -31.2240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7077  -29.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6724  -30.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4343  -28.8918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1211  -29.3387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0823  -30.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7660  -30.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4928  -30.2220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5316  -29.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8436  -28.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8813  -28.1413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6070  -27.7699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6447  -26.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3705  -26.5739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9566  -26.5087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9943  -25.6923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3020  -25.2557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7201  -25.3209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2583  -29.0279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1146  -28.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1724  -30.9749    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.7119  -24.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4181  -24.0893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4103  -23.2725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6976  -22.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9913  -23.2903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0027  -24.1057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1141  -22.8571    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  4  6  1  0
  5  2  1  0
  2  8  1  0
  7  6  1  0
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  6
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11 21  2  0
  7 22  1  6
  8 23  1  1
 20 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 26 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4099730

   ---

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: 458.48

Molecular Weight (Monoisotopic): 457.1980

AlogP: 7.91

#Rotatable Bonds: 5

Polar Surface Area: 29.10

Molecular Species: NEUTRAL

HBA: 1

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 7.68

CX LogD: 7.68

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.35

Np Likeness Score: 1.43

References

1. Idippily ND, Zheng Q, Gan C, Quamine A, Ashcraft MM, Zhong B, Su B..  (2017)  Copalic acid analogs down-regulate androgen receptor and inhibit small chaperone protein.,  27  (11): [PMID:28442254] [10.1016/j.bmcl.2017.04.046]

Source

Source(1):

• Scientific Literature