(8R,9S,10R,13S,14S,16S,E)-17-ethylidene-16-(4-(hydroxymethyl)-1H-1,2,3-triazol-1-yl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

ID: ALA4080181

PubChem CID: 137648514

Max Phase: Preclinical

Molecular Formula: C24H33N3O2

Molecular Weight: 395.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C=C1/[C@@H](n2cc(CO)nn2)C[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C

Standard InChI:  InChI=1S/C24H33N3O2/c1-4-19-22(27-13-16(14-28)25-26-27)12-21-18-6-5-15-11-17(29)7-9-23(15,2)20(18)8-10-24(19,21)3/h4,11,13,18,20-22,28H,5-10,12,14H2,1-3H3/b19-4-/t18-,20+,21+,22+,23+,24-/m1/s1

Standard InChI Key:  GEWYWRATWZGNQX-VJSBNCGGSA-N

Molfile:  

     RDKit          2D

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   18.2960  -18.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2960  -19.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0013  -19.8891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0013  -18.2547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.7031  -19.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4052  -19.8940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1152  -19.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4121  -18.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1187  -18.6783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1355  -17.0386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4174  -17.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.6034  -18.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0954  -17.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6249  -17.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9071  -17.8995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3766  -18.5683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1578  -18.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1711  -17.5071    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.3981  -17.2463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8900  -16.4440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3531  -15.8279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8372  -16.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8207  -19.0926    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.1108  -17.8585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.4050  -19.0761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.6993  -17.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5889  -19.8943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8111  -18.8194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5629  -18.4991    0.0000 O   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  2  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
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  9 12  1  0
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 13 11  1  0
 11 12  1  0
 13 14  1  0
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 15 16  1  0
 16 17  1  0
 17 13  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 18  1  0
 16 18  1  1
 17 23  2  0
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 13 25  1  1
 14 26  1  6
 10 27  1  1
  9 28  1  6
  5 29  1  1
  2 30  2  0
 20 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4080181

   ---

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: 395.55

Molecular Weight (Monoisotopic): 395.2573

AlogP: 4.40

#Rotatable Bonds: 2

Polar Surface Area: 68.01

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.90

CX Basic pKa: ┄

CX LogP: 3.54

CX LogD: 3.54

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.75

Np Likeness Score: 1.36

References

1. Lee D, Kim T, Kim KH, Ham J, Jang TS, Kang KS, Lee JW..  (2017)  Evaluation of guggulsterone derivatives as novel kidney cell protective agents against cisplatin-induced nephrotoxicity.,  27  (14): [PMID:28552338] [10.1016/j.bmcl.2017.05.033]

Source

Source(1):

• Scientific Literature