NP-MRD: Showing NP-Card for petasiphenone (NP0322488)

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Record Information

Version

2.0

Created at

2022-09-12 01:17:10 UTC

Updated at

2022-09-12 01:17:10 UTC

NP-MRD ID

NP0322488

Secondary Accession Numbers

None

Natural Product Identification

Common Name

petasiphenone

Description

3,4-Dihydroxyphenacyl caffeate, also known as petasiphenone, 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. 3,4-Dihydroxyphenacyl caffeate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3,4-Dihydroxyphenacyl caffeate has been detected, but not quantified in, green vegetables. petasiphenone is found in Actaea racemosa and Petasites japonicus. This could make 3,4-dihydroxyphenacyl caffeate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    0.2219   -1.3334    1.1943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3912   -0.3654    0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8343   -0.4823    0.3959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5129    0.5089   -0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9295    0.4478   -0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5514    1.5600   -1.0139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8756    1.6132   -1.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6712    0.4886   -1.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0129    0.5428   -1.4109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0958   -0.6248   -0.5219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8516   -1.7515   -0.2589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7384   -0.6363   -0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3226    0.7730    0.4030 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6959    0.9346    0.6540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5029   -0.0622   -0.0826 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8972   -0.8947   -0.8098 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511   -0.0665    0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5754    0.8614    0.8465 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9531    0.8110    0.9261 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6791   -0.1429    0.2172 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0517   -0.1559    0.3266 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0393   -1.0469   -0.5709 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7470   -2.0038   -1.2839 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6662   -1.0207   -0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3266   -1.4066    0.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9544    1.4165   -0.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9541    2.4490   -1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3509    2.4670   -1.7753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6603   -0.2174   -1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8207   -1.8683   -0.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2850   -1.5152    0.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9411    0.9051    1.7366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9632    1.9686    0.3170 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0507    1.6165    1.4121 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4894    1.5010    1.5318 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6041   -0.8380   -0.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2747   -2.6786   -1.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1902   -1.7535   -1.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 24  2  0
 24 22  1  0
 22 23  1  0
 22 20  2  0
 20 21  1  0
 20 19  1  0
 19 18  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
 18 17  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
  4 26  1  0
  3 25  1  0
 14 32  1  0
 14 33  1  0
 24 38  1  0
 23 37  1  0
 21 36  1  0
 19 35  1  0
 18 34  1  0
  6 27  1  0
  7 28  1  0
M  END


  Mrv0541 05061306052D          

 24 25  0  0  0  0            999 V2000
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    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
   -0.7145    2.0625    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
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   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
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   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
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  5  3  2  0  0  0  0
  6  2  2  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  7  2  0  0  0  0
 11  3  1  0  0  0  0
 11  8  2  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 14  7  1  0  0  0  0
 14 12  2  0  0  0  0
 15  8  1  0  0  0  0
 15 13  2  0  0  0  0
 16  9  1  0  0  0  0
 16 11  1  0  0  0  0
 17  6  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  0  0  0  0
 22 16  2  0  0  0  0
 23 17  2  0  0  0  0
 24  9  1  0  0  0  0
 24 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322488

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(O)C=C(\C=C\C(=O)OCC(=O)C2=CC(O)=C(O)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O7/c18-12-4-1-10(7-14(12)20)2-6-17(23)24-9-16(22)11-3-5-13(19)15(21)8-11/h1-8,18-21H,9H2/b6-2+

> <INCHI_KEY>
DPMVCMFEBYVTFB-QHHAFSJGSA-N

> <FORMULA>
C17H14O7

> <MOLECULAR_WEIGHT>
330.2889

> <EXACT_MASS>
330.073952802

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
32.207653434200246

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.5332747199999996

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.224648986197671

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.795599420719603

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283761206589404

> <JCHEM_POLAR_SURFACE_AREA>
124.29

> <JCHEM_REFRACTIVITY>
85.65429999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.18e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336   6.930   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
CONECT    1    4   10                                                       
CONECT    2    6   10                                                       
CONECT    3    5   11                                                       
CONECT    4    1   12                                                       
CONECT    5    3   13                                                       
CONECT    6    2   17                                                       
CONECT    7   10   14                                                       
CONECT    8   11   15                                                       
CONECT    9   16   24                                                       
CONECT   10    1    2    7                                                  
CONECT   11    3    8   16                                                  
CONECT   12    4   14   18                                                  
CONECT   13    5   15   19                                                  
CONECT   14    7   12   20                                                  
CONECT   15    8   13   21                                                  
CONECT   16    9   11   22                                                  
CONECT   17    6   23   24                                                  
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23   17                                                            
CONECT   24    9   17                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
3,4-Dihydroxyphenacyl caffeic acid	Generator
Petasiphenone	HMDB
3,4-Dihydroxyphenacyl caffeate phenylpropanoid ester	HMDB
2-(3,4-Dihydroxyphenyl)-2-oxoethyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₁₇H₁₄O₇

Average Mass

330.2889 Da

Monoisotopic Mass

330.07395 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC1=C(O)C=C(\C=C\C(=O)OCC(=O)C2=CC(O)=C(O)C=C2)C=C1

InChI Identifier

InChI=1S/C17H14O7/c18-12-4-1-10(7-14(12)20)2-6-17(23)24-9-16(22)11-3-5-13(19)15(21)8-11/h1-8,18-21H,9H2/b6-2+

InChI Key

DPMVCMFEBYVTFB-QHHAFSJGSA-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
Petasites japonicus	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
Benzoyl
Catechol
Styrene
Aryl alkyl ketone
Phenol
Fatty acid ester
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alpha-acyloxy ketone
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
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	2.79	ALOGPS
logP	2.53	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	85.65 m³·mol⁻¹	ChemAxon
Polarizability	32.21 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

HMDB0031706

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008369

KNApSAcK ID

Not Available

Chemspider ID

17226431

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16066851

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for petasiphenone (NP0322488)

MOL for NP0322488 (petasiphenone)

3D MOL for NP0322488 (petasiphenone)

3D SDF for NP0322488 (petasiphenone)

3D-SDF for NP0322488 (petasiphenone)

PDB for NP0322488 (petasiphenone)

3D PDB for NP0322488 (petasiphenone)

SMILES for NP0322488 (petasiphenone)

INCHI for NP0322488 (petasiphenone)

Structure for NP0322488 (petasiphenone)

3D Structure for NP0322488 (petasiphenone)