NP-MRD: Showing NP-Card for Xenognosin A (NP0045407)

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Record Information

Version

2.0

Created at

2022-03-17 19:19:26 UTC

Updated at

2022-03-17 19:19:26 UTC

NP-MRD ID

NP0045407

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xenognosin A

Description

Xenognosin A belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups. Xenognosin A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Xenognosin A has been detected, but not quantified in, common pea and pulses. Xenognosin A is found in Dalbergia parviflora. This could make xenognosin a a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -2.7201   -2.0233   -0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1761   -1.2622    0.1064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3332    0.1167    0.0888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0063    0.7358   -0.9384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1286    2.1083   -0.8982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7862    2.7863   -1.8885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5880    2.8403    0.1482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9194    2.1894    1.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7845    0.8157    1.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0649    0.0826    2.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2996   -0.3487    1.7689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434   -0.0862    0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0587   -0.4779    0.0571 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4196   -0.1387   -1.2554 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6521   -0.5121   -1.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5670   -1.2051   -0.9583 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8173   -1.5871   -1.4132 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1790   -1.5200    0.3221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9569   -1.1667    0.8196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8294   -2.0074   -0.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3574   -3.0761   -0.8026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3088   -1.6510   -1.9170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4389    0.1724   -1.7721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9232    3.7683   -1.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6772    3.9147    0.1907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4854    2.7470    1.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6240   -0.8128    2.4968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9754    0.7712    3.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9119   -0.8811    2.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0981    0.4568   -0.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7089    0.4071   -1.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9658   -0.2635   -2.7319 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1442   -1.3796   -2.3401 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8955   -2.0745    0.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7089   -1.4384    1.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  9  8  1  0
  8  7  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  4  3  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 19 35  1  0
  8 26  1  0
  7 25  1  0
  6 24  1  0
  4 23  1  0
M  END


  Mrv0541 05061304482D          

 19 20  0  0  0  0            999 V2000
    0.0000    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
   -1.4289    2.4750    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
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    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    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 12  3  1  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 13  4  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  2  0  0  0  0
 16 11  1  0  0  0  0
 16 13  2  0  0  0  0
 17 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19  1  1  0  0  0  0
 19 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045407

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C\C=C\C2=CC=C(O)C=C2)C=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O3/c1-19-16-11-15(18)10-7-13(16)4-2-3-12-5-8-14(17)9-6-12/h2-3,5-11,17-18H,4H2,1H3/b3-2+

> <INCHI_KEY>
LOHIEGDVOARVPJ-NSCUHMNNSA-N

> <FORMULA>
C16H16O3

> <MOLECULAR_WEIGHT>
256.2964

> <EXACT_MASS>
256.109944378

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.16779665148322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(2E)-3-(4-hydroxyphenyl)prop-2-en-1-yl]-3-methoxyphenol

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
3.910153607333333

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.79891203201439

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.193427019378618

> <JCHEM_PKA_STRONGEST_BASIC>
-4.846162206458287

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
76.53880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.74e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
xenognosin A

> <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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667  10.780   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    3    4                                                       
CONECT    3    2   12                                                       
CONECT    4    2   13                                                       
CONECT    5    8   12                                                       
CONECT    6    9   12                                                       
CONECT    7   10   13                                                       
CONECT    8    5   14                                                       
CONECT    9    6   14                                                       
CONECT   10    7   15                                                       
CONECT   11   15   16                                                       
CONECT   12    3    5    6                                                  
CONECT   13    4    7   16                                                  
CONECT   14    8    9   17                                                  
CONECT   15   10   11   18                                                  
CONECT   16   11   13   19                                                  
CONECT   17   14                                                            
CONECT   18   15                                                            
CONECT   19    1   16                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
1-(4-Hydroxyphenyl)-3-(4-hydroxy-2-methoxyphenyl)propene	HMDB
4-[3-(4-Hydroxyphenyl)-2-propenyl]-3-methoxyphenol, 9ci	HMDB

Chemical Formula

C₁₆H₁₆O₃

Average Mass

256.2964 Da

Monoisotopic Mass

256.10994 Da

IUPAC Name

4-[(2E)-3-(4-hydroxyphenyl)prop-2-en-1-yl]-3-methoxyphenol

Traditional Name

xenognosin A

CAS Registry Number

76907-79-4

SMILES

COC1=C(C\C=C\C2=CC=C(O)C=C2)C=CC(O)=C1

InChI Identifier

InChI=1S/C16H16O3/c1-19-16-11-15(18)10-7-13(16)4-2-3-12-5-8-14(17)9-6-12/h2-3,5-11,17-18H,4H2,1H3/b3-2+

InChI Key

LOHIEGDVOARVPJ-NSCUHMNNSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Dalbergia parviflora	LOTUS Database	35616633
Pisum sativum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Cinnamylphenols

Direct Parent

Cinnamylphenols

Alternative Parents

Substituents

Cinnamylphenol
Methoxyphenol
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:10075 )

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	3.6	ALOGPS
logP	3.91	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	9.19	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	76.54 m³·mol⁻¹	ChemAxon
Polarizability	28.17 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