NP-MRD: Showing NP-Card for cimiciphenone (NP0242267)

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Record Information

Version

2.0

Created at

2022-09-07 02:33:23 UTC

Updated at

2022-09-07 02:33:23 UTC

NP-MRD ID

NP0242267

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cimiciphenone

Description

Cimiciphenone belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. cimiciphenone is found in Actaea racemosa. cimiciphenone was first documented in 2005 (PMID: 15971118). Based on a literature review very few articles have been published on Cimiciphenone.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 42  0  0  0  0  0  0  0  0999 V2000
    8.2600    0.3265    0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4551   -0.6587    0.0126 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0702   -0.5681    0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4757    0.4452    0.8241 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0873    0.5368    0.9215 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -0.4331    0.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8962   -0.3975    0.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1848    0.5089    0.9735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2987    0.4378    0.9608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9613    1.3077    1.5783 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9624   -0.5525    0.2928 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3552   -0.6941    0.2291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0137    0.4927   -0.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2618    1.4301   -0.7579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4487    0.5686   -0.5582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9957    1.6952   -1.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3421    1.8608   -1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1847    0.8324   -0.9373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5336    1.0250   -1.1535 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6708   -0.3039   -0.3566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4979   -1.3258    0.0452 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3008   -0.4206   -0.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9502   -1.4509   -0.4488 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3154   -1.5297   -0.5368 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9452   -2.5601   -1.2643 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3272    0.0764    0.4543 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0742    0.3269    1.7683 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9788    1.3271    0.2385 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1249    1.1762    1.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6681    1.3459    1.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3371   -1.1802   -0.1975 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6945    1.2868    1.4986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628   -0.8956    1.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5718   -1.5508   -0.4502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3323    2.4865   -1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7493    2.7591   -1.7998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2208    0.3532   -0.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4899   -1.3370   -0.0421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9285   -1.3227    0.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3359   -2.1971   -0.9494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3518   -3.2277   -1.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
  6 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 22 15  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  5 30  1  0
  7 31  1  0
  8 32  1  0
 12 33  1  0
 12 34  1  0
 16 35  1  0
 17 36  1  0
 19 37  1  0
 21 38  1  0
 22 39  1  0
 23 40  1  0
 25 41  1  0
M  END


  Mrv1652309072204332D          

 25 26  0  0  0  0            999 V2000
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  2  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0242267

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(\C=C\C(=O)OCC(=O)C2=CC=C(O)C(O)=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O7/c1-24-17-6-2-11(8-15(17)21)3-7-18(23)25-10-16(22)12-4-5-13(19)14(20)9-12/h2-9,19-21H,10H2,1H3/b7-3+

> <INCHI_KEY>
DAFPSPBZCRCOAU-XVNBXDOJSA-N

> <FORMULA>
C18H16O7

> <MOLECULAR_WEIGHT>
344.319

> <EXACT_MASS>
344.089602855

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
34.334372689951415

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-2-oxoethyl (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
2.679168776

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.82281946931557

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.808490467922851

> <JCHEM_PKA_STRONGEST_BASIC>
-4.884397756219305

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
90.1366

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-2-oxoethyl (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15                                                       
CONECT   23    6   24                                                       
CONECT   24   23    3   25                                                  
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₇

Average Mass

344.3190 Da

Monoisotopic Mass

344.08960 Da

IUPAC Name

2-(3,4-dihydroxyphenyl)-2-oxoethyl (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

Traditional Name

2-(3,4-dihydroxyphenyl)-2-oxoethyl (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(\C=C\C(=O)OCC(=O)C2=CC=C(O)C(O)=C2)C=C1O

InChI Identifier

InChI=1S/C18H16O7/c1-24-17-6-2-11(8-15(17)21)3-7-18(23)25-10-16(22)12-4-5-13(19)14(20)9-12/h2-9,19-21H,10H2,1H3/b7-3+

InChI Key

DAFPSPBZCRCOAU-XVNBXDOJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Actaea racemosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Methoxyphenol
Phenoxy compound
Anisole
Benzoyl
Catechol
Methoxybenzene
Aryl alkyl ketone
Phenol ether
Styrene
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Alpha-acyloxy ketone
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ether
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.68	ChemAxon
pKa (Strongest Acidic)	7.81	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	90.14 m³·mol⁻¹	ChemAxon
Polarizability	34.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

28282835

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71487912

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Stromeier S, Petereit F, Nahrstedt A: Phenolic esters from the rhizomes of Cimicifuga racemosa do not cause proliferation effects in MCF-7 cells. Planta Med. 2005 Jun;71(6):495-500. [PubMed:15971118 ]
LOTUS database [Link]

Showing NP-Card for cimiciphenone (NP0242267)

MOL for NP0242267 (cimiciphenone)

3D MOL for NP0242267 (cimiciphenone)

3D SDF for NP0242267 (cimiciphenone)

3D-SDF for NP0242267 (cimiciphenone)

PDB for NP0242267 (cimiciphenone)

3D PDB for NP0242267 (cimiciphenone)

SMILES for NP0242267 (cimiciphenone)

INCHI for NP0242267 (cimiciphenone)

Structure for NP0242267 (cimiciphenone)

3D Structure for NP0242267 (cimiciphenone)