(5S,10R,13S,17S)-17-((E)-(S)-1-Hydroxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-tetradecahydro-cyclopenta[a]phenanthrene-3,6-dione

ID: ALA1790301

PubChem CID: 56664706

Max Phase: Preclinical

Molecular Formula: C27H42O3

Molecular Weight: 414.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C/C=C/[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3CC(=O)[C@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C

Standard InChI:  InChI=1S/C27H42O3/c1-17(2)7-6-12-27(5,30)24-9-8-20-19-16-23(29)22-15-18(28)10-13-25(22,3)21(19)11-14-26(20,24)4/h6,12,17,19-22,24,30H,7-11,13-16H2,1-5H3/b12-6+/t19-,20-,21-,22+,24-,25+,26-,27-/m0/s1

Standard InChI Key:  NFWKUHWWUWPAOU-HCYXZYOZSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  1  0  0  0  0  0999 V2000
    2.4042   -6.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -4.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8250   -6.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1167   -5.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -5.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4000   -6.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1125   -7.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3375   -4.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8292   -6.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1250   -4.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3250   -5.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -5.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3375   -3.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8125   -5.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6917   -7.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0500   -3.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -8.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -6.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7625   -3.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2667   -7.3292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -6.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4000   -5.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -4.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3292   -2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4750   -3.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1875   -3.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9000   -3.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2000   -4.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3991   -7.9167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2529   -5.1754    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6430   -6.6874    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6896   -6.6024    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2900   -4.3204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 10  1  0
  3  4  1  0
  4  1  1  0
  5  3  1  0
  6  1  1  0
  7  6  1  0
  8  2  1  0
  9  7  1  0
 10 11  1  0
 11  4  1  0
 12  5  1  0
 13  1  1  0
  8 14  1  0
 15 12  1  0
 16  6  1  0
 17 14  1  0
 18  7  2  0
 19 22  1  0
 20 17  2  0
 21 19  2  0
 22 13  1  0
  1 23  1  1
  2 24  1  1
 14 25  1  1
 26 14  1  0
 27 20  1  0
 28 27  1  0
 29 28  1  0
 30 28  1  0
  6 31  1  6
  4 32  1  6
  5 33  1  6
  3 34  1  1
 19 16  1  0
  3  9  1  0
  5  2  1  0
  8 15  1  0
  8 35  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1790301

   (5S,8S,9S,10R,13S,14S,17S)-17-[(E,2S)-2-hydroxy-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,4,5,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6-dione

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: 414.63

Molecular Weight (Monoisotopic): 414.3134

AlogP: 5.75

#Rotatable Bonds: 4

Polar Surface Area: 54.37

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.28

CX LogD: 5.28

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.60

Np Likeness Score: 2.65

References

1. Bultel-Poncé V, Etahiri S, Guyot M..  (2002)  New ketosteroids from the red alga Hypnea musciformis.,  12  (13): [PMID:12067544] [10.1016/s0960-894x(02)00295-0]

Source

Source(1):

• Scientific Literature