Cimicifugic acid N

ID: ALA1094303

PubChem CID: 46210734

Max Phase: Preclinical

Molecular Formula: C22H22O11

Molecular Weight: 462.41

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Cimicifugic Acid N | Cimicifugic acid N|CHEMBL1094303|BDBM50316417

Canonical SMILES:  COc1ccc(/C=C\C(=O)O[C@H](C(=O)O)[C@](O)(Cc2ccc(O)c(O)c2)C(=O)O)cc1OC

Standard InChI:  InChI=1S/C22H22O11/c1-31-16-7-4-12(10-17(16)32-2)5-8-18(25)33-19(20(26)27)22(30,21(28)29)11-13-3-6-14(23)15(24)9-13/h3-10,19,23-24,30H,11H2,1-2H3,(H,26,27)(H,28,29)/b8-5-/t19-,22-/m1/s1

Standard InChI Key:  YMPYAGUNPNITIL-SAEXZTQASA-N

Molfile:  

     RDKit          2D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -3.1139  -17.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1151  -18.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4003  -18.4902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6838  -18.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6867  -17.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4021  -16.8372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9738  -16.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2587  -17.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4552  -16.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458  -17.8208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1449  -17.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2751  -18.6673    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9698  -17.9658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1712  -17.2356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4523  -16.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1653  -15.5858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2636  -15.5908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8841  -16.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6001  -17.2302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8810  -15.9954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8285  -16.8376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8299  -18.4893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3130  -16.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3099  -15.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0238  -15.5793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0210  -14.7550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3045  -14.3444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5892  -14.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5955  -15.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3003  -13.5194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0126  -13.1033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7341  -14.3402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4500  -14.7504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  1 21  1  0
  2  3  1  0
  2 22  1  0
  8 11  1  0
 19 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
  1  2  2  0
 27 28  1  0
  9 14  1  0
 28 29  2  0
 29 24  1  0
  5  7  1  0
 27 30  1  0
  9 15  1  1
 30 31  1  0
  3  4  2  0
 26 32  1  0
 15 16  2  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094303

   CIMICIFUGIC ACID N

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: 462.41

Molecular Weight (Monoisotopic): 462.1162

AlogP: 1.18

#Rotatable Bonds: 10

Polar Surface Area: 180.05

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.98

CX Basic pKa: ┄

CX LogP: 2.37

CX LogD: -4.00

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.19

Np Likeness Score: 1.15

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