Eupachinsin D

ID: ALA4165787

PubChem CID: 145953756

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[C@@H](O)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)30-18-7-11(2)16(25)9-17(28-14(5)24)12(3)8-19-20(18)13(4)21(26)29-19/h6,8,16-20,23,25H,2,4,7,9-10H2,1,3,5H3/b12-8-,15-6-/t16-,17+,18-,19-,20-/m1/s1

Standard InChI Key:  RDTSNPPYNHHXLZ-IDSHBCFPSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
    5.5625  -24.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5625  -25.7789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2744  -24.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9865  -24.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829  -25.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4120  -24.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6987  -24.5421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2019  -26.4206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1250  -26.6372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8765  -27.1405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7420  -26.0939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0132  -25.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3140  -26.1452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9837  -24.8829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4085  -25.7849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8708  -26.4203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3090  -27.1281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1175  -26.9301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1790  -26.1001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7473  -27.4631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8804  -25.6658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1286  -24.5512    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1329  -23.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8496  -23.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4207  -23.3100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5619  -23.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8540  -22.4926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2744  -23.7123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5575  -24.5587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1416  -22.0763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4541  -27.1289    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6207  -26.5789    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  1  0
  4  5  2  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
 24 27  1  0
  3 28  1  1
 26 29  1  0
 27 30  1  0
 16 31  1  1
 15 32  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4165787

   ---

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: ┄

CX Basic pKa: ┄

CX LogP: 1.37

CX LogD: 1.37

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.30

Np Likeness Score: 3.47

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