(2S,4aR,4bR,6R,8S,8aR,10aR)-6-Hydroxy-1,1,4a,8,8a-pentamethyl-7-oxo-8-(3-oxopentyl)tetradecahydro-phenanthren-2-yl acetate

ID: ALA4064979

PubChem CID: 137637923

Max Phase: Preclinical

Molecular Formula: C26H42O5

Molecular Weight: 434.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)CC[C@]1(C)C(=O)[C@H](O)C[C@@H]2[C@@]3(C)CC[C@H](OC(C)=O)C(C)(C)[C@@H]3CC[C@]21C

Standard InChI:  InChI=1S/C26H42O5/c1-8-17(28)9-13-26(7)22(30)18(29)15-20-24(5)12-11-21(31-16(2)27)23(3,4)19(24)10-14-25(20,26)6/h18-21,29H,8-15H2,1-7H3/t18-,19+,20-,21+,24+,25-,26-/m1/s1

Standard InChI Key:  ZQXRPVNZMWLJAD-AHKSPXFHSA-N

Molfile:  

     RDKit          2D

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   32.7872  -20.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3743  -21.6846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6454  -18.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5080  -19.7373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   35.6454  -19.3373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2204  -19.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5080  -20.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9455  -18.0998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1955  -18.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.2204  -20.9748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0830  -20.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3497  -20.9748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   34.2122  -20.1498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   35.6454  -20.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9246  -18.9123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5038  -21.3873    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   34.9413  -17.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.3618  -18.1030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.3579  -19.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0729  -19.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7869  -19.7515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5018  -19.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7858  -20.5764    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.2158  -19.7533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6399  -20.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9208  -20.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6491  -19.7293    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 11  1  0
  9  5  1  0
 10  4  1  0
 11 10  1  0
  2  9  1  0
 12  6  1  0
 13  5  1  0
 14 12  1  0
 15 17  1  0
 15 16  1  1
 17 13  1  0
  5 18  1  1
  8 19  1  6
  7 20  1  6
  6 21  1  1
  8  6  1  0
  9 14  1  0
  2 15  1  0
  9 22  1  6
 10 23  1  1
  4 24  2  0
  7 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  1  0
 16 31  1  0
 31 32  1  0
 31 33  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4064979

   ---

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: 434.62

Molecular Weight (Monoisotopic): 434.3032

AlogP: 4.88

#Rotatable Bonds: 5

Polar Surface Area: 80.67

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.38

CX Basic pKa: ┄

CX LogP: 4.71

CX LogD: 4.71

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.62

Np Likeness Score: 2.57

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