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

ID: ALA2337345

PubChem CID: 71582966

Max Phase: Preclinical

Molecular Formula: C26H43NO

Molecular Weight: 385.64

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](NCc3ccccc3)CC[C@]12C

Standard InChI:  InChI=1S/C26H43NO/c1-19(2)10-9-11-20(3)22-14-16-26(5)24(28)23(15-17-25(22,26)4)27-18-21-12-7-6-8-13-21/h6-8,12-13,19-20,22-24,27-28H,9-11,14-18H2,1-5H3/t20-,22-,23+,24-,25-,26+/m1/s1

Standard InChI Key:  PFQKUMCDIDKGSM-YYUHFVFVSA-N

Molfile:  

     RDKit          2D

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   12.2537   -3.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9590   -3.9044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9590   -2.2700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6643   -2.6837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6653   -3.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4419   -3.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9209   -3.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4402   -2.4305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.6917   -1.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2542   -2.4268    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.4908   -1.4820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1440   -1.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9588   -4.7215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5466   -3.9095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.0384   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8375   -1.9176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3851   -2.5242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1842   -2.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1336   -3.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8383   -3.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1312   -3.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4255   -3.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7188   -3.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7196   -4.7306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4329   -5.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1366   -4.7267    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  6
  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
M  END

Alternative Forms

1. Parent:

   

   ALA2337345

   (1R,3aR,4S,5S,7aR)-5-(benzylamino)-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: 385.64

Molecular Weight (Monoisotopic): 385.3345

AlogP: 6.18

#Rotatable Bonds: 8

Polar Surface Area: 32.26

Molecular Species: BASE

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 9.33

CX LogP: 6.65

CX LogD: 4.74

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.56

Np Likeness Score: 1.24

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