Jatrogrossidione

ID: ALA4213396

PubChem CID: 101804595

Max Phase: Preclinical

Molecular Formula: C20H24O3

Molecular Weight: 312.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@@H](C(=C)C)[C@@H]2C=C(C)C(=O)C3=C(C(=O)[C@@H](C)[C@H]3O)[C@@H]12

Standard InChI:  InChI=1S/C20H24O3/c1-9(2)13-7-6-10(3)15-14(13)8-11(4)18(21)17-16(15)19(22)12(5)20(17)23/h8,12-15,20,23H,1,3,6-7H2,2,4-5H3/t12-,13+,14+,15+,20-/m1/s1

Standard InChI Key:  ZCRHGEOBXMVLID-BINAMKIQSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    9.3745  -17.8076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8975  -18.4712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3812  -19.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1554  -18.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1530  -18.0562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8023  -19.3847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6038  -19.1963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9541  -18.4516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7916  -17.5393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5959  -17.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0917  -16.1495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5368  -16.7593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7378  -16.5879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7844  -18.3538    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.1183  -19.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1324  -19.9082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0803  -18.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4106  -17.7099    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8960  -16.3232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1480  -17.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6251  -20.1825    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1181  -17.0317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9470  -17.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1982  -18.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4949  -16.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  9  1  0
  4  6  1  0
  6  7  1  0
 10  8  1  0
  7  8  2  0
  9 10  1  0
  9 12  1  0
 10 20  1  0
 19 11  1  0
 11 12  1  0
 12 13  2  0
  9 14  1  6
  7 15  1  0
  3 16  1  6
  2 17  1  6
 10 18  1  1
 20 19  1  0
  6 21  2  0
  1 22  2  0
 20 23  1  1
 23 24  1  0
 23 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4213396

   (2S,3R,6aS,7R,10aR)-3-hydroxy-2,5-dimethyl-10-methylidene-7-prop-1-en-2-yl-3,6a,7,8,9,10a-hexahydro-2H-benzo[h]azulene-1,4-dione

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: 312.41

Molecular Weight (Monoisotopic): 312.1725

AlogP: 3.17

#Rotatable Bonds: 1

Polar Surface Area: 54.37

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.91

CX Basic pKa: ┄

CX LogP: 3.35

CX LogD: 3.35

Aromatic Rings: ┄

Heavy Atoms: 23

QED Weighted: 0.76

Np Likeness Score: 2.58

References

1. Zhang CY, Zhang LJ, Lu ZC, Ma CY, Ye Y, Rahman K, Zhang H, Zhu JY..  (2018)  Antitumor Activity of Diterpenoids from Jatropha gossypiifolia: Cell Cycle Arrest and Apoptosis-Inducing Activity in RKO Colon Cancer Cells.,  81  (8): [PMID:30106289] [10.1021/acs.jnatprod.7b01036]

Source

Source(1):

• Scientific Literature