Isocalonysterone

ID: ALA3633595

PubChem CID: 122195388

Max Phase: Preclinical

Molecular Formula: C27H40O7

Molecular Weight: 476.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(O)CC[C@@H](O)[C@](C)(O)[C@H]1CC=C2C3=C(O)C(=O)[C@@H]4C[C@@H](O)[C@@H](O)C[C@]4(C)C3=CC[C@@]21C

Standard InChI:  InChI=1S/C27H40O7/c1-24(2,33)10-9-20(30)27(5,34)19-7-6-14-21-15(8-11-25(14,19)3)26(4)13-18(29)17(28)12-16(26)22(31)23(21)32/h6,8,16-20,28-30,32-34H,7,9-13H2,1-5H3/t16-,17+,18-,19-,20+,25-,26+,27+/m0/s1

Standard InChI Key:  NDANWMYSKQTWFD-LVXUDJRLSA-N

Molfile:  

     RDKit          2D

 36 39  0  0  0  0  0  0  0  0999 V2000
   -4.1792   -0.4015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1792   -1.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9382   -2.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9565    0.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790   -0.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6790   -1.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4197   -2.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8212   -1.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380    0.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8030   -0.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8030    2.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4562    1.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440    1.7885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440    0.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5625    0.3285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5625    1.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3032    2.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5993    3.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9034    2.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9100    1.3104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1993    3.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5033    2.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7992    3.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8350    3.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7926    4.4817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8419    2.6878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2195    0.1967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2209   -2.4390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6930    0.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0413    2.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6351    3.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5927    4.4532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4094   -3.7549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3325    1.5372    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8698   -2.3902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6736   -2.8250    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  2  0
  9 10  1  0
  9 12  2  0
 10 14  1  0
 13 11  1  0
 11 12  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 13  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  1
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  1 27  1  1
  2 28  1  1
  5 29  1  1
 13 30  1  1
 18 31  1  0
 18 32  1  1
  7 33  2  0
 17 34  1  6
  8 35  1  0
  6 36  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3633595

   ---

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: 476.61

Molecular Weight (Monoisotopic): 476.2774

AlogP: 2.47

#Rotatable Bonds: 5

Polar Surface Area: 138.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.02

CX Basic pKa: ┄

CX LogP: 0.28

CX LogD: 0.27

Aromatic Rings: ┄

Heavy Atoms: 34

QED Weighted: 0.36

Np Likeness Score: 2.60

References

1. Csábi J, Hsieh TJ, Hasanpour F, Martins A, Kele Z, Gáti T, Simon A, Tóth G, Hunyadi A..  (2015)  Oxidized Metabolites of 20-Hydroxyecdysone and Their Activity on Skeletal Muscle Cells: Preparation of a Pair of Desmotropes with Opposite Bioactivities.,  78  (10): [PMID:26465254] [10.1021/acs.jnatprod.5b00249]

Source

Source(1):

• Scientific Literature