Cimicifugic acid M

ID: ALA1096937

PubChem CID: 46210733

Max Phase: Preclinical

Molecular Formula: C20H18O9

Molecular Weight: 402.36

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Cimicifugic Acid M | Cimicifugic acid M|CHEMBL1096937|BDBM50316416

Canonical SMILES:  O=C(/C=C/c1ccc(O)c(O)c1)O[C@H](C(=O)O)[C@](O)(Cc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C20H18O9/c21-14-8-6-12(10-15(14)22)7-9-16(23)29-17(18(24)25)20(28,19(26)27)11-13-4-2-1-3-5-13/h1-10,17,21-22,28H,11H2,(H,24,25)(H,26,27)/b9-7+/t17-,20-/m1/s1

Standard InChI Key:  RHQXHDXIEARXSC-DTLVDHMJSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -3.5389  -10.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5401  -10.9898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8253  -11.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1088  -10.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1117  -10.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8271   -9.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3988   -9.7436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837  -10.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0302   -9.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2708  -10.7333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801  -10.8697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7001  -11.5798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5448  -10.8783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7462  -10.1481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0273   -8.9133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7403   -8.4983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6886   -8.5033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591   -9.7329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1751  -10.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4560   -8.9079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8880   -9.7275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6040  -10.1373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6045  -10.9594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3197  -11.3691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0336  -10.9539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0278  -10.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3120   -9.7187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7501  -11.3628    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7392   -9.7069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  7  1  0
  9 15  1  1
  3  4  2  0
 15 16  2  0
  7  8  1  0
 15 17  1  0
 14 18  1  0
  8  9  1  0
 18 19  1  0
  4  5  1  0
 18 20  2  0
  8 10  1  6
 19 21  2  0
  2  3  1  0
 21 22  1  0
  8 11  1  0
 22 23  2  0
  5  6  2  0
 23 24  1  0
 11 12  2  0
 24 25  2  0
  6  1  1  0
 25 26  1  0
 11 13  1  0
 26 27  2  0
 27 22  1  0
  1  2  2  0
 25 28  1  0
  9 14  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1096937

   CIMICIFUGIC ACID M

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: 3.28

CX Basic pKa: ┄

CX LogP: 2.69

CX LogD: -3.36

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.25

Np Likeness Score: 1.21

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