15-Hydroxyeupachinisin D

ID: ALA4176395

PubChem CID: 145973610

Max Phase: Preclinical

Molecular Formula: C22H28O9

Molecular Weight: 436.46

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

Standard InChI:  InChI=1S/C22H28O9/c1-5-14(9-23)22(28)31-18-6-11(2)16(26)8-17(29-13(4)25)15(10-24)7-19-20(18)12(3)21(27)30-19/h5,7,16-20,23-24,26H,2-3,6,8-10H2,1,4H3/b14-5-,15-7-/t16-,17+,18-,19-,20-/m1/s1

Standard InChI Key:  WMEDCDUFTLZNBI-WKFPSNGCSA-N

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
   17.0622  -24.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0622  -25.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7742  -24.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4862  -24.8120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4827  -25.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9117  -24.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1984  -24.4003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7016  -26.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6246  -26.4953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3762  -26.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2418  -25.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5130  -25.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8138  -26.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4834  -24.7410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9082  -25.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3706  -26.2784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8086  -26.9862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6172  -26.7882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6786  -25.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2470  -27.3211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3800  -25.5239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6283  -24.4094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6327  -23.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3492  -23.1756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9204  -23.1681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0616  -23.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3536  -22.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7742  -23.5703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0572  -24.4168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6414  -21.9344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5553  -27.0803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1204  -26.4370    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.1538  -27.0703    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
 10 31  1  0
 15 32  1  6
 16 33  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA4176395

   ---

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: 436.46

Molecular Weight (Monoisotopic): 436.1733

AlogP: 0.50

#Rotatable Bonds: 5

Polar Surface Area: 139.59

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.09

CX LogD: 0.09

Aromatic Rings: ┄

Heavy Atoms: 31

QED Weighted: 0.24

Np Likeness Score: 3.45

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