Jatropholone A

ID: ALA4214497

Cas Number: 71424-66-3

PubChem CID: 14059526

Max Phase: Preclinical

Molecular Formula: C20H24O2

Molecular Weight: 296.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@H]2[C@@H](c3c(C)c(O)c4c(c31)C(=O)[C@@H](C)C4)C2(C)C

Standard InChI:  InChI=1S/C20H24O2/c1-9-6-7-13-17(20(13,4)5)15-11(3)19(22)12-8-10(2)18(21)16(12)14(9)15/h10,13,17,22H,1,6-8H2,2-5H3/t10-,13-,17-/m0/s1

Standard InChI Key:  BMHPRIPRPDSKRK-SVKFGRERSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   36.7200  -16.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1421  -17.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.9350  -17.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5663  -16.2329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8577  -15.8276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1515  -17.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1482  -16.2395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3706  -15.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8933  -16.6528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3759  -17.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8581  -17.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5692  -17.0555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7361  -18.2822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2992  -18.8861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.1219  -18.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3391  -17.3537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5864  -18.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7418  -16.6410    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   36.3733  -18.3497    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   32.9557  -18.5246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1266  -18.0896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8551  -15.0104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2725  -15.8216    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0761  -16.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  6 11  1  0
 12  4  1  0
  4  5  2  0
  5  7  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10  6  1  0
 11 12  2  0
 12 16  1  0
 11 13  1  0
 13 14  1  0
 17 15  1  0
 14 15  1  0
 17 16  1  0
  2 17  1  0
 16  2  1  0
 16 18  1  6
 17 19  1  6
 13 20  2  0
 10 21  2  0
  5 22  1  0
  4 23  1  0
  9 24  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4214497

   Jatropholone A

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: 296.41

Molecular Weight (Monoisotopic): 296.1776

AlogP: 4.62

#Rotatable Bonds: ┄

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.30

CX Basic pKa: ┄

CX LogP: 4.82

CX LogD: 4.81

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.76

Np Likeness Score: 2.51

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