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

ID: ALA4088658

PubChem CID: 137644900

Max Phase: Preclinical

Molecular Formula: C27H39NO

Molecular Weight: 393.62

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)Nc1ccc(C)cc1

Standard InChI:  InChI=1S/C27H39NO/c1-19-8-12-22(13-9-19)28-25(29)18-20(2)10-14-23-21(3)11-15-24-26(4,5)16-7-17-27(23,24)6/h8-9,12-13,18,23-24H,3,7,10-11,14-17H2,1-2,4-6H3,(H,28,29)/b20-18+/t23-,24-,27+/m1/s1

Standard InChI Key:  ITGJUJNSFCLURD-MCCODWFKSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    1.9811  -21.2263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6303  -20.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2213  -21.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9745  -19.1908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9391  -20.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7011  -18.8048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3879  -19.2518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3490  -20.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0327  -20.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7596  -20.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7984  -19.3188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1104  -18.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1480  -18.0544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8738  -17.6830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9115  -16.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6373  -16.4870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2234  -16.4217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2611  -15.6054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5688  -15.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9868  -15.2340    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5251  -18.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3814  -18.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4392  -20.8879    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9786  -14.4164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6849  -14.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6771  -13.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9644  -12.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2581  -13.2033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2695  -14.0188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9551  -11.9659    0.0000 C   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
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088658

   ---

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: 393.62

Molecular Weight (Monoisotopic): 393.3032

AlogP: 7.46

#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: 7.43

CX LogD: 7.43

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.41

Np Likeness Score: 1.52

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