(1R,3aR,4R,5S,7aR)-5-(2,3-Dichlorobenzylamino)-1-((R)-1,5-dimethylhexyl)-3a,7a-dimethyloctahydroinden-4-ol

ID: ALA2336930

PubChem CID: 71583190

Max Phase: Preclinical

Molecular Formula: C26H41Cl2NO

Molecular Weight: 454.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2(C)[C@@H](O)[C@@H](NCc3cccc(Cl)c3Cl)CC[C@]12C

Standard InChI:  InChI=1S/C26H41Cl2NO/c1-17(2)8-6-9-18(3)20-12-14-26(5)24(30)22(13-15-25(20,26)4)29-16-19-10-7-11-21(27)23(19)28/h7,10-11,17-18,20,22,24,29-30H,6,8-9,12-16H2,1-5H3/t18-,20-,22+,24+,25-,26+/m1/s1

Standard InChI Key:  PUWITTDFHMVFTM-ZDDIXMJPSA-N

Molfile:  

     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   24.0040  -27.8588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0040  -28.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7092  -29.0805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7092  -27.4461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4145  -27.8598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4156  -28.6760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1921  -28.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6711  -28.2662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1904  -27.6066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4072  -27.0416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4113  -29.4890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4419  -26.8291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0045  -27.6029    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.2410  -26.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8943  -26.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7090  -29.8976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2968  -29.0856    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7886  -27.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5877  -27.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1353  -27.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9344  -27.5293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8838  -28.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5885  -28.6780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8814  -29.0877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1757  -28.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4691  -29.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4698  -29.9067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1831  -30.3141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8868  -29.9028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5969  -30.3072    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   21.1871  -31.1313    0.0000 Cl  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
 29 30  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2336930

   (1R,3aR,4R,5S,7aR)-5-[(2,3-dichlorophenyl)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: 454.53

Molecular Weight (Monoisotopic): 453.2565

AlogP: 7.49

#Rotatable Bonds: 8

Polar Surface Area: 32.26

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.49

CX LogP: 7.86

CX LogD: 6.73

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.43

Np Likeness Score: 0.84

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