NP-MRD: Showing NP-Card for vestitone (NP0305280)

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Record Information

Version

2.0

Created at

2022-09-10 20:58:29 UTC

Updated at

2022-09-10 20:58:30 UTC

NP-MRD ID

NP0305280

Secondary Accession Numbers

None

Natural Product Identification

Common Name

vestitone

Description

Vestitone, also known as (3R3S)-vestitone, belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Thus, vestitone is considered to be a flavonoid lipid molecule. Vestitone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Vestitone has been detected, but not quantified in, several different foods, such as purslanes, spelts, sea-buckthornberries, cloudberries, and pineappple sages. vestitone is found in Dalbergia parviflora, Erythrina fusca and Melilotus messanensis. This could make vestitone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
    5.8852   -0.1778    0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3256    0.2140   -0.4016 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9319    0.3151   -0.4887 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    0.7110   -1.6585 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9495    0.7999   -1.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1381    0.5141   -0.6092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3135    0.5146   -0.6781 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9883    1.7720   -0.2177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3552    1.7174   -0.6044 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0709    0.5402   -0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4538    0.5768   -0.2386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2383   -0.5399   -0.0036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5966   -0.5085    0.1184 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5707   -1.7700    0.1097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1823   -1.8181   -0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530   -0.6962   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9862   -0.7399   -0.3938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3548   -1.8297   -0.2704 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7769    0.1206    0.5446 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0369   -0.1795    1.6768 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1734    0.0150    0.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5574    0.5095    1.6527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6575   -1.2094    1.1482 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0013    0.0112    0.7031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9763    0.9391   -2.4976 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4889    1.1060   -2.6294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5054    0.6056   -1.8804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4393    2.6490   -0.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    1.8016    0.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9514    1.5683   -0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1078   -1.3704    0.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1169   -2.7006    0.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240   -2.7499    0.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5058   -0.4135    2.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6039   -0.2976    1.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 21  2  0
 21 19  1  0
 19 20  1  0
 19  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 16  2  0
 16 15  1  0
 15 14  2  0
 14 12  1  0
 12 13  1  0
 12 11  2  0
 16 17  1  0
 17 18  2  0
  4  3  1  0
 17  7  1  0
 11 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
 21 35  1  0
 20 34  1  0
  5 26  1  0
  4 25  1  0
  7 27  1  6
  8 28  1  0
  8 29  1  0
 15 33  1  0
 14 32  1  0
 13 31  1  0
 11 30  1  0
M  END


  Mrv0541 05061306022D          

 21 23  0  0  0  0            999 V2000
    7.1447    3.3000    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 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
    4.2868    3.3000    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
    5.7158    2.4750    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
    2.1434    2.0625    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
    5.0013    2.0625    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    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  9  2  1  0  0  0  0
  9  6  2  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 12  4  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  2  0  0  0  0
 15  6  1  0  0  0  0
 15 12  2  0  0  0  0
 16 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17  9  1  0  0  0  0
 18 14  1  0  0  0  0
 19 16  2  0  0  0  0
 20  1  1  0  0  0  0
 20 10  1  0  0  0  0
 21  8  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0305280

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-20-10-3-5-11(14(18)7-10)13-8-21-15-6-9(17)2-4-12(15)16(13)19/h2-7,13,17-18H,8H2,1H3

> <INCHI_KEY>
WQCJOKYOIJVEFN-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.640328365445086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.2235521700000005

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.219038661351457

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.767140798974506

> <JCHEM_PKA_STRONGEST_BASIC>
-4.568658637073049

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
76.15880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.51e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vestitone

> <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      13.337   6.160   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       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    4    9                                                       
CONECT    3    5   10                                                       
CONECT    4    2   12                                                       
CONECT    5    3   11                                                       
CONECT    6    9   15                                                       
CONECT    7   10   14                                                       
CONECT    8   13   21                                                       
CONECT    9    2    6   17                                                  
CONECT   10    3    7   20                                                  
CONECT   11    5   13   14                                                  
CONECT   12    4   15   16                                                  
CONECT   13    8   11   16                                                  
CONECT   14    7   11   18                                                  
CONECT   15    6   12   21                                                  
CONECT   16   12   13   19                                                  
CONECT   17    9                                                            
CONECT   18   14                                                            
CONECT   19   16                                                            
CONECT   20    1   10                                                       
CONECT   21    8   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
(3R3S)-Vestitone	HMDB
2',7-Dihydroxy-4'-methoxyisoflavanone	HMDB
2,3-Dihydro-7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one	HMDB

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2794 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

vestitone

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O

InChI Identifier

InChI=1S/C16H14O5/c1-20-10-3-5-11(14(18)7-10)13-8-21-15-6-9(17)2-4-12(15)16(13)19/h2-7,13,17-18H,8H2,1H3

InChI Key

WQCJOKYOIJVEFN-UHFFFAOYSA-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
Dalbergia parviflora	LOTUS Database	35616633
Erythrina fusca	LOTUS Database	35616633
Melilotus messanensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C4' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

4'-O-methylated isoflavonoids

Alternative Parents

Substituents

4p-methoxyisoflavonoid
Isoflavanol
Hydroxyisoflavonoid
Isoflavanone
Isoflavan
Chromone
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Ketone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050462 )
an isoflavanone (VESTITONE )

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	2.22	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	7.77	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.16 m³·mol⁻¹	ChemAxon
Polarizability	28.64 Å³	ChemAxon
Number of Rings	3	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

HMDB0031620

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008258

KNApSAcK ID

Not Available

Chemspider ID

150159

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

171769

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for vestitone (NP0305280)

MOL for NP0305280 (vestitone)

3D MOL for NP0305280 (vestitone)

3D SDF for NP0305280 (vestitone)

3D-SDF for NP0305280 (vestitone)

PDB for NP0305280 (vestitone)

3D PDB for NP0305280 (vestitone)

SMILES for NP0305280 (vestitone)

INCHI for NP0305280 (vestitone)

Structure for NP0305280 (vestitone)

3D Structure for NP0305280 (vestitone)