(1R,3aR,4R,5S,7aR)-1-((R)-1,5-Dimethylhexyl)-5-(4-methoxybenzylamino)-3a,7a-dimethyloctahydroinden-4-ol

ID: ALA2336931

PubChem CID: 71583191

Max Phase: Preclinical

Molecular Formula: C27H45NO2

Molecular Weight: 415.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CN[C@H]2CC[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@]3(C)[C@H]2O)cc1

Standard InChI:  InChI=1S/C27H45NO2/c1-19(2)8-7-9-20(3)23-14-16-27(5)25(29)24(15-17-26(23,27)4)28-18-21-10-12-22(30-6)13-11-21/h10-13,19-20,23-25,28-29H,7-9,14-18H2,1-6H3/t20-,23-,24+,25+,26-,27+/m1/s1

Standard InChI Key:  ZIUGFPRXGAUHOU-XOXNVLTOSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    4.9651   -3.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9651   -4.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6703   -5.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6703   -3.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3756   -3.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3767   -4.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1532   -4.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6322   -4.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1515   -3.6563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3683   -3.0913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3724   -5.5387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4030   -2.8788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9656   -3.6526    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2021   -2.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8554   -2.2722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6701   -5.9473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2579   -5.1353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7497   -3.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5488   -3.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0964   -3.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8955   -3.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8449   -4.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5496   -4.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8425   -5.1374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1368   -4.7294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4301   -5.1383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4309   -5.9564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442   -6.3638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8479   -5.9525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243   -6.3669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0155   -5.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9  5  1  0
  5 10  1  1
  6 11  1  6
  9 12  1  0
  9 13  1  6
 12 14  1  0
 12 15  1  6
  3 16  1  1
  2 17  1  1
 14 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 17 23  1  0
 23 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
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2336931

   (1R,3aR,4R,5S,7aR)-5-[(4-methoxyphenyl)methylamino]-3a,7a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7-hexahydro-1H-inden-4-ol

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: 415.66

Molecular Weight (Monoisotopic): 415.3450

AlogP: 6.19

#Rotatable Bonds: 9

Polar Surface Area: 41.49

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.24

CX LogP: 6.49

CX LogD: 4.66

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.50

Np Likeness Score: 1.15

References

1. König M, Müller C, Bracher F..  (2013)  Stereoselective synthesis of a new class of potent and selective inhibitors of human Δ8,7-sterol isomerase.,  21  (7): [PMID:23433667] [10.1016/j.bmc.2013.01.041]

Source

Source(1):

• Scientific Literature