Cimicifugic acid K

ID: ALA1096631

PubChem CID: 46210731

Max Phase: Preclinical

Molecular Formula: C20H18O9

Molecular Weight: 402.36

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Cimicifugic Acid K | Cimicifugic acid K|CHEMBL1096631|BDBM50316414

Canonical SMILES:  O=C(/C=C/c1ccc(O)cc1)O[C@H](C(=O)O)[C@](O)(Cc1ccc(O)cc1)C(=O)O

Standard InChI:  InChI=1S/C20H18O9/c21-14-6-1-12(2-7-14)5-10-16(23)29-17(18(24)25)20(28,19(26)27)11-13-3-8-15(22)9-4-13/h1-10,17,21-22,28H,11H2,(H,24,25)(H,26,27)/b10-5+/t17-,20-/m1/s1

Standard InChI Key:  BNBCNSZOUCPLOA-HHSWOIGYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -3.4098   -0.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4109   -1.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6961   -1.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9797   -1.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9825   -0.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6979    0.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1257   -1.5309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2696    0.1272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5545   -0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1593    0.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1417   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1510   -0.9989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5709   -1.7090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6740   -1.0075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753   -0.2772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1564    0.9576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8695    1.3726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5595    1.3676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5883    0.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3043   -0.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5851    0.9630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0172    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7332   -0.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7337   -1.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4488   -1.4983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1627   -1.0831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1570   -0.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4412    0.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8793   -1.4919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0
 10 15  1  0
  3  4  2  0
 10 16  1  1
  5  8  1  0
 16 17  2  0
 16 18  1  0
  8  9  1  0
 15 19  1  0
  4  5  1  0
 19 20  1  0
  9 10  1  0
 19 21  2  0
  2  3  1  0
 20 22  2  0
  9 11  1  6
 22 23  1  0
  5  6  2  0
 23 24  2  0
  9 12  1  0
 24 25  1  0
  6  1  1  0
 25 26  2  0
 12 13  2  0
 26 27  1  0
  1  2  2  0
 27 28  2  0
 28 23  1  0
 12 14  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096631

   CIMICIFUGIC ACID K

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: 402.36

Molecular Weight (Monoisotopic): 402.0951

AlogP: 1.17

#Rotatable Bonds: 8

Polar Surface Area: 161.59

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.23

CX Basic pKa: ┄

CX LogP: 2.69

CX LogD: -3.40

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.32

Np Likeness Score: 1.11

References

1. Iwanaga A, Kusano G, Warashina T, Miyase T..  (2010)  Phenolic constituents of the aerial parts of Cimicifuga simplex and Cimicifuga japonica.,  73  (4): [PMID:20184336] [10.1021/np900752t]

Source

Source(1):

• Scientific Literature