NP-MRD: Showing NP-Card for Isovestitol (NP0045927)

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Record Information

Version

2.0

Created at

2022-03-17 19:45:32 UTC

Updated at

2022-03-17 19:45:32 UTC

NP-MRD ID

NP0045927

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isovestitol

Description

Isovestitol belongs to the class of organic compounds known as 2'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C2' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one. Thus, isovestitol is considered to be a flavonoid lipid molecule. Isovestitol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Isovestitol has been detected, but not quantified in, hyacinth beans and pulses. Isovestitol is found in Anthyllis spp., Anthyllis vulneraria , Erythrina sandwicensis, Gliricidia sepium , Lablab niger, Robinia pseudoacacia, Tetragonolobus spp. and Trifolium spp.. This could make isovestitol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305182D          

 20 22  0  0  0  0            999 V2000
    4.2868   -1.6500    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
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    5.7158    0.0000    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    1.2375    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   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
 10  2  1  0  0  0  0
 10  6  1  0  0  0  0
 11  6  1  0  0  0  0
 11  9  1  0  0  0  0
 12  3  1  0  0  0  0
 12  7  2  0  0  0  0
 13  4  1  0  0  0  0
 13  8  2  0  0  0  0
 14  5  1  0  0  0  0
 14 11  1  0  0  0  0
 15  7  1  0  0  0  0
 15 10  2  0  0  0  0
 16  8  1  0  0  0  0
 16 14  2  0  0  0  0
 17 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19  1  1  0  0  0  0
 19 16  1  0  0  0  0
 20  9  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045927

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O4/c1-19-16-8-13(18)4-5-14(16)11-6-10-2-3-12(17)7-15(10)20-9-11/h2-5,7-8,11,17-18H,6,9H2,1H3

> <INCHI_KEY>
FFDNYMAHNWBKCH-UHFFFAOYSA-N

> <FORMULA>
C16H16O4

> <MOLECULAR_WEIGHT>
272.2958

> <EXACT_MASS>
272.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.062652238540494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
3.0340066116666664

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.050560759699131

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.4456766572023

> <JCHEM_PKA_STRONGEST_BASIC>
-4.547089480394376

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
75.42340000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.87e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isovestitol

> <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       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   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       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    3   10                                                       
CONECT    3    2   12                                                       
CONECT    4    5   13                                                       
CONECT    5    4   14                                                       
CONECT    6   10   11                                                       
CONECT    7   12   15                                                       
CONECT    8   13   16                                                       
CONECT    9   11   20                                                       
CONECT   10    2    6   15                                                  
CONECT   11    6    9   14                                                  
CONECT   12    3    7   17                                                  
CONECT   13    4    8   18                                                  
CONECT   14    5   11   16                                                  
CONECT   15    7   10   20                                                  
CONECT   16    8   14   19                                                  
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19    1   16                                                       
CONECT   20    9   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
4',7-Dihydroxy-2'-methoxyisoflavan	HMDB
7,4'-Dihydroxy-2'-methoxyisoflavan	HMDB

Chemical Formula

C₁₆H₁₆O₄

Average Mass

272.2958 Da

Monoisotopic Mass

272.10486 Da

IUPAC Name

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

Traditional Name

isovestitol

CAS Registry Number

63631-42-5

SMILES

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

InChI Identifier

InChI=1S/C16H16O4/c1-19-16-8-13(18)4-5-14(16)11-6-10-2-3-12(17)7-15(10)20-9-11/h2-5,7-8,11,17-18H,6,9H2,1H3

InChI Key

FFDNYMAHNWBKCH-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, 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
Anthyllis spp.	Plant	KNApSAcK
Anthyllis vulneraria	Plant	KNApSAcK
Erythrina sandwicensis	Plant	KNApSAcK
Gliricidia sepium	Plant	KNApSAcK
Lablab niger	Plant	KNApSAcK
Lablab purpureus	FooDB	KNAPSACK
Robinia pseudoacacia	LOTUS Database	35616633
Tetragonolobus spp.	-	KNApSAcK
Trifolium spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C2' 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

2'-O-methylated isoflavonoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavans (LMPK12080028 )

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	2.93	ALOGPS
logP	3.03	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.45	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	75.42 m³·mol⁻¹	ChemAxon
Polarizability	29.06 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

HMDB0030526

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002398

KNApSAcK ID

C00009709

Chemspider ID

514489

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

591830

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isovestitol (NP0045927)

MOL for NP0045927 (Isovestitol)

3D MOL for NP0045927 (Isovestitol)

3D SDF for NP0045927 (Isovestitol)

3D-SDF for NP0045927 (Isovestitol)

PDB for NP0045927 (Isovestitol)

3D PDB for NP0045927 (Isovestitol)

SMILES for NP0045927 (Isovestitol)

INCHI for NP0045927 (Isovestitol)

Structure for NP0045927 (Isovestitol)

3D Structure for NP0045927 (Isovestitol)