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

ID: ALA4069473

PubChem CID: 137632182

Max Phase: Preclinical

Molecular Formula: C27H39N3O

Molecular Weight: 421.63

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H39N3O/c1-5-7-8-19-17-30(29-28-19)25-16-24-21-10-9-18-15-20(31)11-13-26(18,3)23(21)12-14-27(24,4)22(25)6-2/h6,15,17,21,23-25H,5,7-14,16H2,1-4H3/b22-6-/t21-,23+,24+,25+,26+,27-/m1/s1

Standard InChI Key:  XTWQQTAJTVNUKG-JXXWFFNZSA-N

Molfile:  

     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   16.8143  -11.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8143  -12.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5237  -12.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5237  -11.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2331  -11.4654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2297  -12.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9359  -12.6961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6500  -12.2927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9428  -11.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6535  -11.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6704   -9.8283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9481  -10.2303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3811  -10.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3678  -11.0698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1423  -11.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6385  -10.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.4543  -10.6933    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9280  -11.3663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7133  -11.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7265  -10.2969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9494  -10.0360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4331   -9.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8921   -8.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3761   -9.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3596  -11.8905    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.6456  -10.6524    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.9357  -11.8740    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.2258  -10.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1031  -12.6964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3662  -11.6139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1211  -11.2914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7800  -11.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5350  -11.4577    0.0000 C   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
  9 10  1  0
  9 12  1  0
 10 14  1  0
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 13 14  1  0
 14 15  1  0
 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
 23 24  1  0
 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
 32 33  1  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4069473

   ---

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: 421.63

Molecular Weight (Monoisotopic): 421.3093

AlogP: 6.25

#Rotatable Bonds: 4

Polar Surface Area: 47.78

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 0.54

CX LogP: 5.95

CX LogD: 5.95

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.54

Np Likeness Score: 1.15

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