Jatrogossone C; (+)-(4E,2R,3R,6R,9S,11R,13R,15S)-3-acetoxylathyr-4-ene-7,14-dione

ID: ALA4217375

PubChem CID: 145972868

Max Phase: Preclinical

Molecular Formula: C22H32O4

Molecular Weight: 360.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@H]1/C2=C/[C@@H](C)C(=O)C[C@H]3[C@@H](C[C@@H](C)C(=O)[C@H]2C[C@H]1C)C3(C)C

Standard InChI:  InChI=1S/C22H32O4/c1-11-7-16-15(8-13(3)21(16)26-14(4)23)20(25)12(2)9-17-18(10-19(11)24)22(17,5)6/h7,11-13,15,17-18,21H,8-10H2,1-6H3/b16-7+/t11-,12-,13-,15+,17-,18+,21-/m1/s1

Standard InChI Key:  KGBOFDMUICMLTL-IBCDYQSBSA-N

Molfile:  

     RDKit          2D

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   24.1154   -3.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9083   -3.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3230   -2.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5376   -3.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8068   -4.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5951   -4.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6346   -3.6196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8707   -3.3298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3592   -3.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1727   -5.0105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9610   -5.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7493   -5.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9630   -6.0381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0365   -2.9056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6202   -2.2024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8536   -2.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5553   -3.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3005   -5.5818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3271   -4.4244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3188   -2.0223    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.4174   -2.8230    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.5429   -3.9273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5170   -5.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7104   -5.5453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4205   -6.3094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1936   -4.9123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0600   -2.1008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2433   -4.0406    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  1  0
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  7 11  2  0
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 12 13  1  0
 12 14  1  6
  8 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 13 19  2  0
 13 20  1  0
 20  5  1  0
 18  4  1  0
  4 21  1  6
  8 22  1  1
 10 23  1  6
  6 24  1  6
 24 25  1  0
 25 26  1  0
 25 27  2  0
 17 28  1  6
  5 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4217375

   ---

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: 360.49

Molecular Weight (Monoisotopic): 360.2301

AlogP: 3.98

#Rotatable Bonds: 1

Polar Surface Area: 60.44

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.85

CX LogD: 3.85

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.52

Np Likeness Score: 2.52

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