Cannogenol

ID: ALA3122165

PubChem CID: 11872742

Max Phase: Preclinical

Molecular Formula: C23H34O5

Molecular Weight: 390.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@H]3[C@@H](CC[C@@H]4C[C@@H](O)CC[C@@]43CO)[C@@]1(O)CC[C@@H]2C1=CC(=O)OC1

Standard InChI:  InChI=1S/C23H34O5/c1-21-7-5-18-19(3-2-15-11-16(25)4-8-22(15,18)13-24)23(21,27)9-6-17(21)14-10-20(26)28-12-14/h10,15-19,24-25,27H,2-9,11-13H2,1H3/t15-,16+,17-,18+,19-,21-,22-,23+/m1/s1

Standard InChI Key:  CDMVQQAHEQVSMF-NNNAONFXSA-N

Molfile:  

     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
   13.1229   -4.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7059   -7.0165    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1268   -4.5456    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8517   -3.3123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9970   -4.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2850   -6.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4191   -4.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1343   -5.3734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4289   -2.4407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5711   -6.6091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7017   -4.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8575   -4.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8494   -4.9624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7024   -2.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6446   -3.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6314   -5.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9071   -3.1129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9970   -6.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4212   -6.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4142   -5.7790    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.6943   -2.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1357   -6.1938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7091   -5.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2850   -5.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7101   -6.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8435   -5.7873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9202   -1.7780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1423   -3.7190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3746   -1.5623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4057   -4.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9904   -4.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 28 30  1  0
  7 30  1  0
 23 11  1  1
  1 15  1  0
 13 26  1  1
 16  1  1  0
 13 16  1  0
 14 29  2  0
 25  2  1  1
 12 28  1  0
 23  5  1  0
 14 27  1  0
 21 14  1  0
 12  4  1  1
 24  5  1  0
 17 21  2  0
 27  9  1  0
  7 20  1  6
 22  8  1  0
 19 22  1  0
  7  8  1  0
  6 18  1  0
 12 13  1  0
 25 19  1  0
  8  3  1  1
  8 13  1  0
  9 17  1  0
 23 25  1  0
 23  7  1  0
 15 17  1  1
 15 12  1  0
 24  6  1  0
 18 25  1  0
  6 10  1  1
 11 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3122165

   3-[(3S,5R,8R,9S,10R,13R,14S,17R)-3,14-dihydroxy-10-(hydroxymethyl)-13-methyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

Molecule Features

Natural Product: Yes

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: 390.52

Molecular Weight (Monoisotopic): 390.2406

AlogP: 2.58

#Rotatable Bonds: 2

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.88

CX Basic pKa: 0.28

CX LogP: 1.79

CX LogD: 1.79

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: 3.36

References

1. Shi LS, Kuo SC, Sun HD, Morris-Natschke SL, Lee KH, Wu TS..  (2014)  Cytotoxic cardiac glycosides and coumarins from Antiaris toxicaria.,  22  (6): [PMID:24582402] [10.1016/j.bmc.2014.01.052]

Source

Source(1):

• Scientific Literature