Eupachinisin A-2-acetate

ID: ALA4174630

PubChem CID: 145949979

Max Phase: Preclinical

Molecular Formula: C24H30O9

Molecular Weight: 462.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1C(=O)O[C@@H]2/C=C(/C)[C@@H](OC(C)=O)[C@H](OC(C)=O)/C=C(\C)C[C@@H](OC(=O)/C(=C\C)CO)[C@@H]12

Standard InChI:  InChI=1S/C24H30O9/c1-7-17(11-25)24(29)33-18-8-12(2)9-20(30-15(5)26)22(31-16(6)27)13(3)10-19-21(18)14(4)23(28)32-19/h7,9-10,18-22,25H,4,8,11H2,1-3,5-6H3/b12-9+,13-10-,17-7-/t18-,19-,20-,21-,22-/m1/s1

Standard InChI Key:  ABVAZWPWQGQNIB-QSPOTSNMSA-N

Molfile:  

     RDKit          2D

 35 36  0  0  0  0  0  0  0  0999 V2000
   17.5040   -6.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5040   -7.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2160   -5.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9280   -6.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9245   -7.1999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3535   -6.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6403   -5.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1434   -7.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0665   -8.0583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8181   -8.5615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6836   -7.5150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9548   -7.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2556   -7.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9252   -6.3039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3501   -7.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8123   -7.8413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2505   -8.5491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0591   -8.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1205   -7.5210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6889   -8.8841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8219   -7.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0702   -5.9723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0746   -5.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7911   -4.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3622   -4.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5035   -5.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4991   -5.9797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7955   -3.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0832   -3.4974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7883   -5.9645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7859   -5.1396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0702   -4.7291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4991   -4.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5623   -7.9999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.5957   -8.6332    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  4  3  2  0
  4  5  1  0
  4  7  1  0
 15  6  1  0
  6  7  1  0
  2  8  1  0
  8  9  2  0
  9 16  1  0
  8 10  1  0
  2 11  1  1
 11 12  1  0
 12 13  1  0
 12 14  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 15 19  1  0
 18 20  2  0
 19 21  2  0
  6 22  1  1
 22 23  1  0
 23 24  1  0
 23 25  2  0
 24 26  2  0
 26 27  1  0
 24 28  1  0
 28 29  1  0
  1 30  1  6
 30 31  1  0
 31 32  2  0
 31 33  1  0
 15 34  1  6
 16 35  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4174630

   ---

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: 462.50

Molecular Weight (Monoisotopic): 462.1890

AlogP: 2.09

#Rotatable Bonds: 5

Polar Surface Area: 125.43

Molecular Species: NEUTRAL

HBA: 9

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.14

CX LogD: 2.14

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.28

Np Likeness Score: 3.02

References

1. Yu X, Zhang Q, Tian L, Guo Z, Liu C, Chen J, Ebrahim W, Liu Z, Proksch P, Zou K..  (2018)  Germacrane-Type Sesquiterpenoids with Antiproliferative Activities from Eupatorium chinense.,  81  (1): [PMID:29280632] [10.1021/acs.jnatprod.7b00693]

Source

Source(1):

• Scientific Literature