Eupachinsin A

ID: ALA4167418

PubChem CID: 139051650

Max Phase: Preclinical

Molecular Formula: C22H28O8

Molecular Weight: 420.46

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](O)/C=C(\C)C[C@@H](OC(=O)/C(=C\C)CO)[C@@H]12

Standard InChI:  InChI=1S/C22H28O8/c1-6-15(10-23)22(27)30-17-8-11(2)7-16(25)20(28-14(5)24)12(3)9-18-19(17)13(4)21(26)29-18/h6-7,9,16-20,23,25H,4,8,10H2,1-3,5H3/b11-7+,12-9-,15-6-/t16-,17-,18-,19-,20-/m1/s1

Standard InChI Key:  JINQTWSVNPNCHU-QMGPOFJLSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
    4.7291   -6.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7291   -7.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4411   -5.8582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1531   -6.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1496   -7.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5786   -6.2809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8653   -5.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3685   -7.7415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2915   -7.9582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0431   -8.4615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9087   -7.4148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1799   -7.0283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4807   -7.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1504   -6.2038    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5752   -7.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0375   -7.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4755   -8.4491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2842   -8.2510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3455   -7.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9139   -8.7840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0470   -6.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2953   -5.8722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2996   -5.0473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0162   -4.6385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5873   -4.6309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7285   -5.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7242   -5.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0205   -3.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3083   -3.3973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0134   -5.8645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8207   -8.5332    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7874   -7.8998    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
 16 31  1  1
 15 32  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4167418

   ---

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: 420.46

Molecular Weight (Monoisotopic): 420.1784

AlogP: 1.52

#Rotatable Bonds: 4

Polar Surface Area: 119.36

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.70

CX Basic pKa: ┄

CX LogP: 1.69

CX LogD: 1.69

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.30

Np Likeness Score: 3.19

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