NP-MRD: Showing NP-Card for Kievitone (NP0047900)

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Record Information

Version

2.0

Created at

2022-03-17 20:47:47 UTC

Updated at

2022-03-17 20:47:47 UTC

NP-MRD ID

NP0047900

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Kievitone

Description

Kievitone, also known as vignatin, belongs to the class of organic compounds known as 8-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 8-position. Thus, kievitone is considered to be a flavonoid lipid molecule. A hydroxyisoflavanone that is isoflavanone with hydroxy substituents at positions 5, 7, 2' and 4' and a prenyl group at position 8. Kievitone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Kievitone has been detected, but not quantified in, several different foods, such as yellow wax beans, mung beans, scarlet beans, adzuki beans, and cowpea. Kievitone is found in Desmodium gangeticum , Diphysa robinioides, Dipogon lignosus, Lablab niger, Macroptilium bracteatum, Macroptilium lathyroides, Macroptilium martii, Mucuna pruriens , Phaseolus aureus , Phaseolus lunatus , Sphenostylis angustifolia, Sphenostylis stenocarpa , Strongylodon macrobotrys, Strophostyles helvola, Vigna mungo and Dolichos biflorus . Kievitone was first documented in 1988 (PMID: 16665944). This could make kievitone a potential biomarker for the consumption of these foods (PMID: 21133423) (PMID: 7794275).

Structure

MOL SDF PDB SMILES InChI

Kievitone
  Mrv1652309281723292D          

 26 28  0  0  1  0            999 V2000
    5.1955    0.5095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1859   -2.0225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7435   -1.9939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3145    0.4810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9366   -2.4236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7944   -2.4347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9429   -0.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9429    0.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4579   -0.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955   -1.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4579    0.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6557   -1.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7435    0.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7435   -1.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7435    1.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0290    0.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6526   -2.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0290   -0.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3718   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0290    1.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3655   -2.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0847   -1.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0815   -2.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0290    2.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3145    2.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7435    2.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 11  1  0  0  0  0
  2 10  2  0  0  0  0
  3 14  1  0  0  0  0
  4 16  1  0  0  0  0
  5 17  1  0  0  0  0
  6 23  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  7 12  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 14  2  0  0  0  0
 11 13  2  0  0  0  0
 12 17  2  0  0  0  0
 12 19  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 18  1  0  0  0  0
 15 20  1  0  0  0  0
 16 18  2  0  0  0  0
 17 21  1  0  0  0  0
 19 22  2  0  0  0  0
 20 24  2  0  0  0  0
 21 23  2  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END

Kievitone
  Mrv1652309281723292D          

 26 28  0  0  1  0            999 V2000
    5.1955    0.5095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1859   -2.0225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7435   -1.9939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3145    0.4810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9366   -2.4236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7944   -2.4347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9429   -0.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9429    0.0855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4579   -0.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955   -1.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4579    0.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6557   -1.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7435    0.4810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7435   -1.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7435    1.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0290    0.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6526   -2.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0290   -0.7565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3718   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0290    1.7184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3655   -2.4291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0847   -1.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0815   -2.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0290    2.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3145    2.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7435    2.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 11  1  0  0  0  0
  2 10  2  0  0  0  0
  3 14  1  0  0  0  0
  4 16  1  0  0  0  0
  5 17  1  0  0  0  0
  6 23  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  7 12  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 14  2  0  0  0  0
 11 13  2  0  0  0  0
 12 17  2  0  0  0  0
 12 19  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  1  0  0  0  0
 14 18  1  0  0  0  0
 15 20  1  0  0  0  0
 16 18  2  0  0  0  0
 17 21  1  0  0  0  0
 19 22  2  0  0  0  0
 20 24  2  0  0  0  0
 21 23  2  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047900

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C2OCC(C(=O)C2=C(O)C=C1O)C1=C(O)C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O6/c1-10(2)3-5-13-16(23)8-17(24)18-19(25)14(9-26-20(13)18)12-6-4-11(21)7-15(12)22/h3-4,6-8,14,21-24H,5,9H2,1-2H3

> <INCHI_KEY>
MERHMOCEIBOOMA-UHFFFAOYSA-N

> <FORMULA>
C20H20O6

> <MOLECULAR_WEIGHT>
356.3692

> <EXACT_MASS>
356.125988372

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
36.69143171786884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
4.152659791666666

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.940918209839648

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.66464296974757

> <JCHEM_PKA_STRONGEST_BASIC>
-4.926771890286203

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
97.90019999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
kievitone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Kievitone                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-SEP-17         0                                  
HETATM    1  O   UNK     0       9.698   0.951   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.680  -3.775   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       6.988  -3.722   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       4.320   0.898   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.082  -4.524   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      16.416  -4.545   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      11.093  -1.444   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.093   0.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.321  -1.412   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.698  -2.236   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.321   0.128   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.424  -2.219   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.988   0.898   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.988  -2.182   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.988   2.438   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.654   0.128   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.418  -3.759   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.654  -1.412   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.761  -1.454   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.654   3.208   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.749  -4.534   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.091  -2.229   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.085  -3.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.654   4.748   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.320   5.518   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.988   5.518   0.000  0.00  0.00           C+0
CONECT    1    8   11                                                       
CONECT    2   10                                                            
CONECT    3   14                                                            
CONECT    4   16                                                            
CONECT    5   17                                                            
CONECT    6   23                                                            
CONECT    7    8   10   12                                                  
CONECT    8    1    7                                                       
CONECT    9   10   11   14                                                  
CONECT   10    2    7    9                                                  
CONECT   11    1    9   13                                                  
CONECT   12    7   17   19                                                  
CONECT   13   11   15   16                                                  
CONECT   14    3    9   18                                                  
CONECT   15   13   20                                                       
CONECT   16    4   13   18                                                  
CONECT   17    5   12   21                                                  
CONECT   18   14   16                                                       
CONECT   19   12   22                                                       
CONECT   20   15   24                                                       
CONECT   21   17   23                                                       
CONECT   22   19   23                                                       
CONECT   23    6   21   22                                                  
CONECT   24   20   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
3-(2,4-Dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9ci	HMDB
Phaseolus substance II	HMDB
Vignatin	HMDB

Chemical Formula

C₂₀H₂₀O₆

Average Mass

356.3692 Da

Monoisotopic Mass

356.12599 Da

IUPAC Name

3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

kievitone

CAS Registry Number

40105-60-0

SMILES

CC(C)=CCC1=C2OCC(C(=O)C2=C(O)C=C1O)C1=C(O)C=C(O)C=C1

InChI Identifier

InChI=1S/C20H20O6/c1-10(2)3-5-13-16(23)8-17(24)18-19(25)14(9-26-20(13)18)12-6-4-11(21)7-15(12)22/h3-4,6-8,14,21-24H,5,9H2,1-2H3

InChI Key

MERHMOCEIBOOMA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Desmodium gangeticum	Plant	KNApSAcK
Diphysa robinioides	Plant	KNApSAcK
Dipogon lignosus	Plant	KNApSAcK
Lablab niger	Plant	KNApSAcK
Lablab purpureus	FooDB	KNAPSACK
Macroptilium bracteatum	Plant	KNApSAcK
Macroptilium lathyroides	Plant	KNApSAcK
Macroptilium martii	Plant	KNApSAcK
Mucuna pruriens	Plant	KNApSAcK
Phaseolus aureus	Plant	KNApSAcK
Phaseolus coccineus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus lunatus	Plant	KNApSAcK
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sphenostylis angustifolia	Plant	KNApSAcK
Sphenostylis stenocarpa	Plant	KNApSAcK
Strongylodon macrobotrys	Plant	KNApSAcK
Strophostyles helvola	Plant	KNApSAcK
Vigna angularis	FooDB	KNAPSACK
Vigna mungo	LOTUS Database	35616633
Vigna radiata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vigna umbellata	FooDB	KNAPSACK
Vigna unguiculata	FooDB	KNAPSACK
Vigna unguiculata ssp. cylindrica	Plant	KNApSAcK
Vigna unguiculata ssp. unguiculata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

8-prenylated isoflavanones

Alternative Parents

Substituents

8-prenylated isoflavanone
Isoflavanol
Hydroxyisoflavonoid
Chromone
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Resorcinol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavanone (CHEBI:16832 )
isoflavanones (C01590 )
Isoflavonoids (C01590 )
Isoflavonoids (LMPK12050479 )

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	2.99	ALOGPS
logP	4.15	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	7.66	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.9 m³·mol⁻¹	ChemAxon
Polarizability	36.69 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

HMDB0034213

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

119269

PDB ID

Not Available

ChEBI ID

16832

Good Scents ID

Not Available

References

General References

Rogers KR, Albert F, Anderson AJ: Lipid peroxidation is a consequence of elicitor activity. Plant Physiol. 1988 Feb;86(2):547-53. doi: 10.1104/pp.86.2.547. [PubMed:16665944 ]
Boue SM, Burow ME, Wiese TE, Shih BY, Elliott S, Carter-Wientjes CH, McLachlan JA, Bhatnagar D: Estrogenic and antiestrogenic activities of phytoalexins from red kidney bean (Phaseolus vulgaris L.). J Agric Food Chem. 2011 Jan 12;59(1):112-20. doi: 10.1021/jf102255u. Epub 2010 Dec 6. [PubMed:21133423 ]
Hoffman R: Potent inhibition of breast cancer cell lines by the isoflavonoid kievitone: comparison with genistein. Biochem Biophys Res Commun. 1995 Jun 15;211(2):600-6. doi: 10.1006/bbrc.1995.1855. [PubMed:7794275 ]

Showing NP-Card for Kievitone (NP0047900)

MOL for NP0047900 (Kievitone)

3D MOL for NP0047900 (Kievitone)

3D SDF for NP0047900 (Kievitone)

3D-SDF for NP0047900 (Kievitone)

PDB for NP0047900 (Kievitone)

3D PDB for NP0047900 (Kievitone)

SMILES for NP0047900 (Kievitone)

INCHI for NP0047900 (Kievitone)

Structure for NP0047900 (Kievitone)

3D Structure for NP0047900 (Kievitone)