(2R,3R,5S,7S,8S,9S,13S,14S)-14-benzoyloxy-5,7-diisobutanoyloxy-2,3,8,9-tetraacetoxy-jatropha-jatropha-6(17),4E,11E-triene

ID: ALA5285398

Max Phase: Preclinical

Molecular Formula: C43H60O12

Molecular Weight: 768.94

Names and Identifiers

Canonical SMILES:  C=C1[C@H](OCC(C)C)C2=C(C[C@@](C)(OC(C)=O)[C@@H]2OC(C)=O)[C@@H](OC(=O)c2ccccc2)[C@@H](C)/C=C/C(C)(C)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OCC(C)C

Standard InChI:  InChI=1S/C43H60O12/c1-24(2)22-49-36-27(6)37(50-23-25(3)4)38(51-28(7)44)40(53-30(9)46)42(11,12)20-19-26(5)35(54-41(48)32-17-15-14-16-18-32)33-21-43(13,55-31(10)47)39(34(33)36)52-29(8)45/h14-20,24-26,35-40H,6,21-23H2,1-5,7-13H3/b20-19+/t26-,35-,36-,37-,38+,39+,40+,43+/m0/s1

Standard InChI Key:  JGNMEJACWCUVLB-OLYATILXSA-N

Molfile:  

 
     RDKit          2D

 55 57  0  0  0  0  0  0  0  0999 V2000
   -1.8498   -0.6580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5173   -0.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2624    0.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4373    0.6116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1822   -0.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0646    1.3431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2797    1.5981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4081    1.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4506   -0.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2333    1.1379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3464   -0.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9299   -0.9157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7551   -0.9157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2293   -0.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1420    0.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9687    0.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5562    1.2949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0661    2.3952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6481    1.9267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3159    0.0408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1015   -0.7559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8887   -1.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4730   -2.1361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0917   -1.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8498   -1.4832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1352   -1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1352   -2.7210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4205   -1.4832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381   -1.2604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4506   -1.9751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381   -2.6898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4506   -3.4044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423   -2.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7163   -1.7128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2998   -2.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0862   -3.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6697   -3.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2891   -3.3070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1676   -1.6304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9929   -1.6304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4055   -2.3450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4055   -0.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0264   -0.5676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6100    0.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4071   -0.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5526    0.8129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4451    1.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0286    2.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6586    0.9160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8259    2.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4071    2.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1933    3.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4007    3.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8141    3.0972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5598    0.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  1  1  0
  4  6  1  0
  7  6  1  0
  8  7  1  0
  5  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 10 15  1  0
 15 16  1  0
 15 17  1  0
  7 18  1  1
  6 19  1  1
  2 20  1  1
  2 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
  1 25  1  1
 25 26  1  0
 26 27  1  0
 26 28  2  0
  9 29  1  6
 29 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 12 34  1  1
 34 35  1  0
 35 36  1  0
 36 37  1  0
 36 38  1  0
 13 39  1  6
 39 40  1  0
 40 41  1  0
 40 42  2  0
 14 43  1  6
 43 44  1  0
 44 45  1  0
 44 46  2  0
 19 47  1  0
 47 48  1  0
 47 49  2  0
 50 48  2  0
 51 50  1  0
 52 51  2  0
 53 52  1  0
 54 53  2  0
 48 54  1  0
 11 55  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5285398

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 768.94

Molecular Weight (Monoisotopic): 768.4085

AlogP: 6.90

#Rotatable Bonds: 12

Polar Surface Area: 149.96

Molecular Species: NEUTRAL

HBA: 12

HBD: ┄

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 6.45

CX LogD: 6.45

Aromatic Rings: 1

Heavy Atoms: 55

QED Weighted: 0.12

Np Likeness Score: 1.50

References

1. Maimaitijiang A, Wang B, Yang H, Tang D, Liu Y, Aisa HA..  (2022)  Discovery of a novel highly potent and low-toxic jatrophane derivative enhancing the P-glycoprotein-mediated doxorubicin sensitivity of MCF-7/ADR cells.,  244  [PMID:36242992] [10.1016/j.ejmech.2022.114822]

Source

Source(1):

• Scientific Literature