(3S,5R,8R,9R,10R,12R,14S)-4,4,8,10,14-Pentamethyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,12-diol

ID: ALA4084460

PubChem CID: 137647281

Max Phase: Preclinical

Molecular Formula: C22H36O2

Molecular Weight: 332.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)[C@@H](O)CC[C@]2(C)[C@H]3C[C@@H](O)C4=CCC[C@@]4(C)[C@]3(C)CC[C@@H]12

Standard InChI:  InChI=1S/C22H36O2/c1-19(2)16-8-12-22(5)17(20(16,3)11-9-18(19)24)13-15(23)14-7-6-10-21(14,22)4/h7,15-18,23-24H,6,8-13H2,1-5H3/t15-,16+,17-,18+,20+,21-,22-/m1/s1

Standard InChI Key:  ZEXFZUOFFMSVBL-PEOBBCQRSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   11.1962   -6.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7878   -5.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3747   -6.6418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6472   -3.4681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5089   -4.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9261   -4.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6472   -4.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2217   -4.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5089   -5.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9470   -3.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4351   -3.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1967   -3.3806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4267   -4.5561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9261   -5.5314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7878   -4.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9228   -3.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2217   -5.9316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0834   -5.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3497   -5.9316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0834   -4.6936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5089   -3.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2134   -5.1063    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6472   -5.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9261   -3.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5048   -6.3442    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.9428   -2.2301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  8  1  0
  6  7  1  0
  7  4  1  0
  8 12  1  0
  9  5  1  0
 10  4  1  0
 11  4  2  0
 12 10  1  0
  2  9  1  0
 13  7  1  0
 14  6  1  0
 15  5  1  0
 16 11  1  0
 17 14  1  0
 18 20  1  0
 18 19  1  1
 20 15  1  0
  5 21  1  1
  8 22  1  6
  7 23  1  6
  6 24  1  1
 13 16  1  0
  8  6  1  0
  9 17  1  0
  2 18  1  0
  9 25  1  6
 10 26  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4084460

   ---

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: 332.53

Molecular Weight (Monoisotopic): 332.2715

AlogP: 4.70

#Rotatable Bonds: ┄

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.84

CX LogD: 3.84

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.63

Np Likeness Score: 3.18

References

1. Shao LD, Bao Y, Shen Y, Su J, Leng Y, Zhao QS..  (2017)  Synthesis of selective 11β-HSD1 inhibitors based on dammarane scaffold.,  135  [PMID:28458137] [10.1016/j.ejmech.2017.04.059]

Source

Source(1):

• Scientific Literature