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

ID: ALA2068917

PubChem CID: 70682437

Max Phase: Preclinical

Molecular Formula: C23H36O4

Molecular Weight: 376.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=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/C23H36O4/c1-21-11-9-17(24)14-16(21)4-6-19-18(21)10-12-22(2)15(5-7-20(25)27-3)8-13-23(19,22)26/h5,7,15-19,24,26H,4,6,8-14H2,1-3H3/b7-5+/t15-,16+,17-,18-,19+,21-,22+,23-/m0/s1

Standard InChI Key:  KJQKBHZKDSBIPI-IFYJLNHVSA-N

Molfile:  

     RDKit          2D

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    4.2208   -6.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583   -7.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1792   -6.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.7042   -5.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7833   -6.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792   -6.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1333   -6.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5792   -5.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7708   -4.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1708   -7.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1333   -7.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2083   -7.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3708   -4.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6208   -7.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6208   -7.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2208   -5.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6542   -6.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3583   -4.6167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1042   -7.9542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7542   -5.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8083   -8.4000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750   -7.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -6.4625    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  1
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 13  4  1  0
 14 10  2  0
 15 14  1  0
 16 13  1  0
 17  6  1  0
 18  8  1  0
  1 19  1  1
 20 15  2  0
 21 11  1  0
 22 17  1  0
  2 23  1  1
  3 24  1  1
 25 15  1  0
 22 26  1  1
 27 25  1  0
  6 28  1  1
 18 12  1  0
  7  9  1  0
  3  6  1  0
 21 22  1  0
  5 29  1  6
  2  1  1  0
  4 30  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA2068917

   methyl (E)-3beta,14beta-dihydroxy-5beta-pregn-20-ene-21-carboxylate

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: 376.54

Molecular Weight (Monoisotopic): 376.2614

AlogP: 3.85

#Rotatable Bonds: 2

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.24

CX LogP: 3.59

CX LogD: 3.59

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.57

Np Likeness Score: 2.52

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