(E)-3-((3S,5R,10S,13S,14S,17S)-3,14-Dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-acrylic acid 2-dimethylamino-ethyl ester

ID: ALA2068987

PubChem CID: 70686668

Max Phase: Preclinical

Molecular Formula: C26H43NO4

Molecular Weight: 433.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)CCOC(=O)/C=C/[C@@H]1CC[C@]2(O)[C@@H]3CC[C@@H]4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@@]12C

Standard InChI:  InChI=1S/C26H43NO4/c1-24-12-10-20(28)17-19(24)5-7-22-21(24)11-13-25(2)18(9-14-26(22,25)30)6-8-23(29)31-16-15-27(3)4/h6,8,18-22,28,30H,5,7,9-17H2,1-4H3/b8-6+/t18-,19-,20+,21+,22-,24+,25+,26+/m1/s1

Standard InChI Key:  LLIUJEHOUCQWGP-ZUSQELBCSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  1  0  0  0  0  0999 V2000
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    8.0917   -5.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792   -3.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3333   -8.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -5.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -6.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7292   -4.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0375   -8.5667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5417   -4.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9000   -4.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8167   -5.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000   -9.1750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8125   -7.7417    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5125   -6.5042    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  5  1  0
  4  1  1  0
  5  4  1  0
  6 16  1  0
  7  2  1  0
  8  1  1  0
  9  5  1  0
 12 10  1  6
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 17  6  1  0
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  1 19  1  1
 20 15  2  0
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 22 29  1  0
 23 15  1  0
 24 17  1  0
  2 25  1  6
  3 26  1  1
 27 23  1  0
 24 28  1  1
 29 27  1  0
 30 22  1  0
 31 22  1  0
  6 32  1  1
 18 12  1  0
  7  9  1  0
  3  6  1  0
 21 24  1  0
  5 33  1  6
  2  1  1  0
  4 34  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2068987

   2-(dimethylamino)ethyl (E)-3-[(3S,5R,8R,9S,10S,13S,14S,17S)-3,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]prop-2-enoate

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: 433.63

Molecular Weight (Monoisotopic): 433.3192

AlogP: 3.78

#Rotatable Bonds: 5

Polar Surface Area: 70.00

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.42

CX LogP: 3.60

CX LogD: 2.55

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.51

Np Likeness Score: 1.99

References

1. De Munari S, Barassi P, Cerri A, Fedrizzi G, Gobbini M, Mabilia M, Melloni P..  (1998)  A new approach to the design of novel inhibitors of Na+,K+-ATPase: 17alpha-substituted seco-D 5beta-androstane as cassaine analogues.,  41  (16): [PMID:9685243] [10.1021/jm980108d]

Source

Source(1):

• Scientific Literature