Jiyuan Oridonin A

ID: ALA4247084

PubChem CID: 145986009

Max Phase: Preclinical

Molecular Formula: C20H28O5

Molecular Weight: 348.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)[C@]23[C@H](O)[C@H]1C[C@H](O)[C@H]2[C@]12CCCC(C)(C)[C@H]1C[C@H]3O[C@H]2O

Standard InChI:  InChI=1S/C20H28O5/c1-9-10-7-11(21)14-19-6-4-5-18(2,3)12(19)8-13(25-17(19)24)20(14,15(9)22)16(10)23/h10-14,16-17,21,23-24H,1,4-8H2,2-3H3/t10-,11-,12+,13+,14-,16+,17+,19-,20+/m0/s1

Standard InChI Key:  IMCRQBUQWXZEDV-OBHPAOCOSA-N

Molfile:  

     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    3.7922  -23.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7922  -23.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5051  -24.3342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5051  -22.6822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2180  -23.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2144  -23.9254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9241  -24.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6418  -23.9314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9311  -22.6871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6414  -23.1079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3570  -22.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3687  -21.8806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6584  -21.4597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9365  -21.8638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3508  -23.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0808  -22.2901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0683  -23.1161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7942  -22.7031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0641  -23.9337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2253  -21.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6415  -22.2691    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2106  -22.2734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9240  -23.5166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2065  -24.7472    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0843  -25.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9102  -25.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4930  -21.8604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3563  -24.3439    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3687  -21.0556    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  1
  5  6  1  0
  5  9  1  0
  6  7  1  0
  7  8  1  0
  8 10  1  0
  9 10  1  0
  9 14  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 10 15  1  1
 12 16  1  0
 15 16  1  0
 11 17  1  1
 16 18  2  0
 15 19  2  0
 14 20  1  1
  9 21  1  1
  5 22  1  0
  8 23  1  0
 22 23  1  0
  6 24  1  1
  3 25  1  0
  3 26  1  0
 22 27  1  6
  8 28  1  6
 12 29  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4247084

   ---

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: 348.44

Molecular Weight (Monoisotopic): 348.1937

AlogP: 1.40

#Rotatable Bonds: ┄

Polar Surface Area: 86.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.93

CX Basic pKa: ┄

CX LogP: 1.29

CX LogD: 1.29

Aromatic Rings: ┄

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: 3.82

References

1. Ke Y, Wang W, Zhao LF, Liang JJ, Liu Y, Zhang X, Feng K, Liu HM..  (2018)  Design, synthesis and biological mechanisms research on 1,2,3-triazole derivatives of Jiyuan Oridonin A.,  26  (17): [PMID:30143365] [10.1016/j.bmc.2017.11.005]

2. Ke Y, Liang JJ, Hou RJ, Li MM, Zhao LF, Wang W, Liu Y, Xie H, Yang RH, Hu TX, Wang JY, Liu HM..  (2018)  Synthesis and biological evaluation of novel Jiyuan Oridonin A-1,2,3-triazole-azole derivatives as antiproliferative agents.,  157  [PMID:30193221] [10.1016/j.ejmech.2018.08.056]

3. Zhou C, Zhang JY, Liu HB, Tian XY, Liu Y, Wang YL, Zheng ZJ, Wang N, Wang ZJ, Xu X, Liu HM, Ke Y..  (2022)  Synthesis, biological evaluation and cellular localization study of fluorescent derivatives of Jiyuan Oridonin A.,  229  [PMID:34954589] [10.1016/j.ejmech.2021.114048]

Source

Source(1):

• Scientific Literature