Cimicifugic acid L

ID: ALA1097937

PubChem CID: 46210732

Max Phase: Preclinical

Molecular Formula: C22H22O10

Molecular Weight: 446.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Cimicifugic Acid L | Cimicifugic acid L|CHEMBL1097937|BDBM50316415

Canonical SMILES:  COc1ccc(/C=C/C(=O)O[C@H](C(=O)O)[C@](O)(Cc2ccc(O)cc2)C(=O)O)cc1OC

Standard InChI:  InChI=1S/C22H22O10/c1-30-16-9-5-13(11-17(16)31-2)6-10-18(24)32-19(20(25)26)22(29,21(27)28)12-14-3-7-15(23)8-4-14/h3-11,19,23,29H,12H2,1-2H3,(H,25,26)(H,27,28)/b10-6+/t19-,22-/m1/s1

Standard InChI Key:  SQGQTKZMNQBRTK-GWJBRELFSA-N

Molfile:  

     RDKit          2D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -3.0056   -5.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0068   -6.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2919   -6.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5755   -6.0227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5784   -5.1922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2937   -4.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7216   -6.4351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8654   -4.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1504   -5.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5635   -4.7716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7375   -5.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2532   -5.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1667   -6.6132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0782   -5.9117    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2795   -5.1814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -3.9466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2736   -3.5316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553   -3.5366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9924   -4.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7084   -5.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9893   -3.9412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4214   -4.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1374   -5.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1378   -5.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8530   -6.4025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5669   -5.9872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5611   -5.1580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8454   -4.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2835   -6.3961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2726   -4.7403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9900   -5.1476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9958   -5.9800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  2  7  1  0
 27 30  1  0
 10 15  1  0
 30 31  1  0
  3  4  2  0
 29 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1097937

   CIMICIFUGIC ACID L

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: 446.41

Molecular Weight (Monoisotopic): 446.1213

AlogP: 1.48

#Rotatable Bonds: 10

Polar Surface Area: 159.82

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.11

CX Basic pKa: ┄

CX LogP: 2.68

CX LogD: -3.56

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.31

Np Likeness Score: 1.01

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