NP-MRD: Showing NP-Card for Isoferreirin (NP0045390)

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Record Information

Version

2.0

Created at

2022-03-17 19:19:08 UTC

Updated at

2022-03-17 19:19:08 UTC

NP-MRD ID

NP0045390

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isoferreirin

Description

Isoferreirin 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, isoferreirin is considered to be a flavonoid lipid molecule. Isoferreirin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Isoferreirin has been detected, but not quantified in, a few different foods, such as fruits, lima beans, and scarlet beans. Isoferreirin is found in Flemingia macrophylla, Stizolobium deeringianum, Uraria picta , Vigna mungo and Dolichos biflorus . This could make isoferreirin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -3.9570   -2.2503    0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2337   -1.1866    0.1027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7626    0.0033   -0.0933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5140    1.1486   -0.0944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9592    2.3953   -0.3334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8040    3.5190   -0.3232 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6071    2.4627   -0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8019    1.3355   -0.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3937    0.1415   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5194   -1.0807   -0.1784 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1127   -1.3368   -1.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4090   -0.9912   -1.7297 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349   -0.6071   -0.7990 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6309   -0.3573   -1.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5482    0.0284   -0.1964 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8754    0.2789   -0.5712 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1681    0.1666    1.1238 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625   -0.0879    1.4720 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5169    0.0585    2.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9159   -0.4822    0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5351   -0.7590    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2077   -0.7312    2.0704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5770   -3.2261   -0.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0569   -2.4936    1.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0277   -2.2335   -0.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5713    1.0248    0.0996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0028    4.0550    0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1808    3.4518   -0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2664    1.4713   -0.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1026   -1.9052    0.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0411   -2.4594   -1.7373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5494   -0.9186   -2.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9441   -0.4624   -2.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1594    1.2218   -0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9116    0.4854    1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814    0.3208    3.5154 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  8  1  0
  8  7  2  0
  7  5  1  0
  5  6  1  0
  5  4  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21 22  2  0
  4  3  1  0
 21 10  1  0
 20 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  8 29  1  0
  7 28  1  0
  6 27  1  0
  4 26  1  0
 10 30  1  1
 11 31  1  0
 11 32  1  0
 14 33  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
M  END

  Mrv0541 05061304472D          

 22 24  0  0  0  0            999 V2000
    4.2868    0.8250    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
    4.2868    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
    5.7158    2.4750    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
    3.5724    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
    0.7145    1.2375    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
    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
    2.1434    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
    6.4302    3.7125    0.0000 O   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
    1.4289    3.3000    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
    5.0013    1.2375    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
  3  2  2  0  0  0  0
  8  2  1  0  0  0  0
  8  5  2  0  0  0  0
  9  4  2  0  0  0  0
  9  6  1  0  0  0  0
 10  3  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  2  0  0  0  0
 15 12  2  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 18  9  1  0  0  0  0
 19 12  1  0  0  0  0
 20 16  2  0  0  0  0
 21  1  1  0  0  0  0
 21 13  1  0  0  0  0
 22  7  1  0  0  0  0
 22 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045390

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C=CC(O)=C1)C1COC2=CC(O)=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O6/c1-21-13-5-8(17)2-3-10(13)11-7-22-14-6-9(18)4-12(19)15(14)16(11)20/h2-6,11,17-19H,7H2,1H3

> <INCHI_KEY>
VODZWHSRITUHNI-UHFFFAOYSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.2788

> <EXACT_MASS>
302.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.630596849961336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-(4-hydroxy-2-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.5699868483333326

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.432385299310093

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.893577284696494

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8648991031021565

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
78.1397

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isoferreirin

> <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   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   4.620   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       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.669   6.160   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       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   3.850   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      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3    8                                                       
CONECT    3    2   10                                                       
CONECT    4    9   12                                                       
CONECT    5    8   13                                                       
CONECT    6    9   14                                                       
CONECT    7   11   22                                                       
CONECT    8    2    5   17                                                  
CONECT    9    4    6   18                                                  
CONECT   10    3   11   13                                                  
CONECT   11    7   10   16                                                  
CONECT   12    4   15   19                                                  
CONECT   13    5   10   21                                                  
CONECT   14    6   15   22                                                  
CONECT   15   12   14   16                                                  
CONECT   16   11   15   20                                                  
CONECT   17    8                                                            
CONECT   18    9                                                            
CONECT   19   12                                                            
CONECT   20   16                                                            
CONECT   21    1   13                                                       
CONECT   22    7   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
4',5,7-Trihydroxy-2'-methoxyisoflavanone	HMDB

Chemical Formula

C₁₆H₁₄O₆

Average Mass

302.2788 Da

Monoisotopic Mass

302.07904 Da

IUPAC Name

5,7-dihydroxy-3-(4-hydroxy-2-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

isoferreirin

CAS Registry Number

76656-75-2

SMILES

COC1=C(C=CC(O)=C1)C1COC2=CC(O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C16H14O6/c1-21-13-5-8(17)2-3-10(13)11-7-22-14-6-9(18)4-12(19)15(14)16(11)20/h2-6,11,17-19H,7H2,1H3

InChI Key

VODZWHSRITUHNI-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
Flemingia macrophylla	LOTUS Database	35616633
Phaseolus coccineus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus lunatus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Stizolobium deeringianum	-	KNApSAcK
Uraria picta	Plant	KNApSAcK
Vigna mungo	LOTUS Database	35616633
Vigna unguiculata ssp. cylindrica	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
Isoflavanol
Isoflavanone
Hydroxyisoflavonoid
Isoflavan
Chromone
Methoxyphenol
Benzopyran
1-benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Phenol ether
Phenoxy compound
Methoxybenzene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050503 )

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	2.48	ALOGPS
logP	2.57	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.89	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.14 m³·mol⁻¹	ChemAxon
Polarizability	29.63 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

HMDB0029491

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000623

KNApSAcK ID

C00009554

Chemspider ID

137998

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156743

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isoferreirin (NP0045390)

MOL for NP0045390 (Isoferreirin)

3D MOL for NP0045390 (Isoferreirin)

3D SDF for NP0045390 (Isoferreirin)

3D-SDF for NP0045390 (Isoferreirin)

PDB for NP0045390 (Isoferreirin)

3D PDB for NP0045390 (Isoferreirin)

SMILES for NP0045390 (Isoferreirin)

INCHI for NP0045390 (Isoferreirin)

Structure for NP0045390 (Isoferreirin)

3D Structure for NP0045390 (Isoferreirin)