(3S,5R,6R,8S,9S,10R,13S,14S)-10-(hydroxymethyl)-13-methylhexadecahydro-1H-cyclopenta[a]phenanthrene-3,5,6-triol

ID: ALA4082424

PubChem CID: 132917086

Max Phase: Preclinical

Molecular Formula: C19H32O4

Molecular Weight: 324.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]12CCC[C@H]1[C@@H]1C[C@@H](O)[C@@]3(O)C[C@@H](O)CC[C@]3(CO)[C@H]1CC2

Standard InChI:  InChI=1S/C19H32O4/c1-17-6-2-3-14(17)13-9-16(22)19(23)10-12(21)4-8-18(19,11-20)15(13)5-7-17/h12-16,20-23H,2-11H2,1H3/t12-,13-,14-,15-,16+,17-,18-,19-/m0/s1

Standard InChI Key:  CJBVCRHFXVRNFQ-QWQVMCIESA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
    1.4487  -26.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4487  -27.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1581  -28.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1581  -26.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8633  -26.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8599  -27.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5661  -28.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2802  -27.7740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5730  -26.5347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2798  -26.9552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2966  -25.3163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5783  -25.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0034  -25.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9945  -26.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7699  -26.8146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2596  -26.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7842  -25.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9981  -24.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8519  -28.5852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5615  -28.9986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7374  -28.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8560  -26.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1447  -25.7190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2717  -26.1336    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5659  -27.3553    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9898  -27.3718    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
  9 12  1  0
 10 14  1  0
 13 11  1  0
 11 12  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 13 18  1  1
  6 19  1  6
  7 20  1  1
  2 21  1  1
  5 22  1  1
 22 23  1  0
 10 24  1  1
  9 25  1  6
 14 26  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4082424

   ---

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: 324.46

Molecular Weight (Monoisotopic): 324.2301

AlogP: 1.84

#Rotatable Bonds: 1

Polar Surface Area: 80.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.22

CX Basic pKa: ┄

CX LogP: 0.85

CX LogD: 0.85

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.59

Np Likeness Score: 3.09

References

1. Endo S, Xia S, Suyama M, Morikawa Y, Oguri H, Hu D, Ao Y, Takahara S, Horino Y, Hayakawa Y, Watanabe Y, Gouda H, Hara A, Kuwata K, Toyooka N, Matsunaga T, Ikari A..  (2017)  Synthesis of Potent and Selective Inhibitors of Aldo-Keto Reductase 1B10 and Their Efficacy against Proliferation, Metastasis, and Cisplatin Resistance of Lung Cancer Cells.,  60  (20): [PMID:28976752] [10.1021/acs.jmedchem.7b00830]

Source

Source(1):

• Scientific Literature