Jatropholone B

ID: ALA4215026

Cas Number: 71386-38-4

PubChem CID: 14059527

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+/m1/s1

Standard InChI Key:  BMHPRIPRPDSKRK-PGQWDYDZSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  0  0  0  0  0  0999 V2000
   29.3033  -17.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7255  -17.7223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5184  -17.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1497  -16.4227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4411  -16.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7348  -17.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7315  -16.4294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9540  -16.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4766  -16.8427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9593  -17.5013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4415  -17.6549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1525  -17.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3195  -18.4721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8826  -19.0760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7052  -19.0101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9225  -17.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1697  -18.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3252  -16.8308    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   28.9566  -18.5395    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.5390  -18.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7099  -18.2795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.4385  -15.2003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.8559  -16.0115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6595  -16.8460    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  6
M  END

Alternative Forms

1. Parent:

   

   ALA4215026

   jatropholone B

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