(3S,5R,8R,9R,10R,14S)-3-Hydroxy-4,4,8,10,14-pentamethyl-1,2,3,4,5,6,7,8,9,10,11,14,15,16-tetradeca-hydro-12H-cyclopenta[a]phenanthren-12-one

ID: ALA4103361

PubChem CID: 137656441

Max Phase: Preclinical

Molecular Formula: C22H34O2

Molecular Weight: 330.51

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H34O2/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/h7,16-18,24H,6,8-13H2,1-5H3/t16-,17+,18-,20-,21+,22+/m0/s1

Standard InChI Key:  MLDXUANBJWSMDT-JPKYEYPISA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   24.6218   -6.1148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2134   -5.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8004   -6.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0728   -2.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9345   -4.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3517   -4.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0728   -3.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6472   -3.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9345   -4.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3726   -2.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8606   -2.6886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6223   -2.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8522   -4.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3517   -5.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2134   -3.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3483   -3.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6472   -5.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5090   -4.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7754   -5.4021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5090   -4.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9345   -3.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6389   -4.5767    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   27.0728   -4.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3517   -3.3388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9304   -5.8147    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   26.3683   -1.7006    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  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103361

   ---

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: 330.51

Molecular Weight (Monoisotopic): 330.2559

AlogP: 4.91

#Rotatable Bonds: ┄

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.40

CX LogD: 4.40

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.69

Np Likeness Score: 3.05

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