Eupachinsin C

ID: ALA4167827

PubChem CID: 145953639

Max Phase: Preclinical

Molecular Formula: C22H28O7

Molecular Weight: 404.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H28O7/c1-6-13(3)21(25)28-18-9-12(2)7-8-17(27-15(5)24)16(11-23)10-19-20(18)14(4)22(26)29-19/h6-7,10,17-20,23H,4,8-9,11H2,1-3,5H3/b12-7+,13-6+,16-10-/t17-,18+,19+,20+/m0/s1

Standard InChI Key:  MUZYRVFSXXFTOF-IMYVKFHPSA-N

Molfile:  

     RDKit          2D

 31 32  0  0  0  0  0  0  0  0999 V2000
   16.3748  -16.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3748  -16.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0868  -15.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7988  -16.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7953  -16.8623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2244  -16.0433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5110  -15.6255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0142  -17.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9372  -17.7206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6888  -18.2239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5544  -17.1772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8256  -16.7907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1264  -17.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7960  -15.9662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2209  -16.8683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6832  -17.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1213  -18.2115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9299  -18.0134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9912  -17.1834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5596  -18.5464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6927  -16.7491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9410  -15.6346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9453  -14.8097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6619  -14.4009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2330  -14.3933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3742  -14.8171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6662  -13.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8679  -18.3055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0908  -14.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4331  -17.6622    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.4664  -18.2956    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
 24 27  1  0
 10 28  1  0
 26 29  1  0
 15 30  1  6
 16 31  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4167827

   ---

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: 404.46

Molecular Weight (Monoisotopic): 404.1835

AlogP: 2.55

#Rotatable Bonds: 4

Polar Surface Area: 99.13

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.61

CX LogD: 2.61

Aromatic Rings: ┄

Heavy Atoms: 29

QED Weighted: 0.33

Np Likeness Score: 3.24

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