NP-MRD: Showing NP-Card for Luteone (NP0048547)

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Record Information

Version

2.0

Created at

2022-03-17 20:58:11 UTC

Updated at

2022-03-17 20:58:11 UTC

NP-MRD ID

NP0048547

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Luteone

Description

Luteone, also known as ruizgenin, belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position. Thus, luteone is considered to be a flavonoid lipid molecule. Luteone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Luteone has been detected, but not quantified in, several different foods, such as common beans, lima beans, pulses, and white lupines. Luteone is found in Argyrocytisus battandieri, Glycyrrhiza glabra , Glycyrrhiza uralensis , Hardenbergia violacea, Laburnum anagyroides , Lupinus ananeanus, Lupinus arboreus, Lupinus arcticus, Lupinus elegans, Lupinus luteus , Lupinus mexicanus, Lupinus micranthus, Lupinus pubescens, Lupinus rivularis, Lupinus spp., Lupinus subcarnosus, Pueraria phaseoloides , Sophora flavescens and Vandasina retusa. Luteone was first documented in 2010 (PMID: 20568784). This could make luteone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309132D          

 26 28  0  0  0  0            999 V2000
   -2.1434    2.0625    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
   -0.7145    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
    0.0000    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
    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
   -1.4289    2.4750    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
    0.7145    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
    0.7145    1.2375    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
    1.4289    2.4750    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
    5.0013    1.2375    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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  2  0  0  0  0
 11  4  1  0  0  0  0
 11  7  2  0  0  0  0
 12  6  1  0  0  0  0
 13  5  1  0  0  0  0
 14  9  2  0  0  0  0
 14 12  1  0  0  0  0
 15  7  1  0  0  0  0
 15 12  2  0  0  0  0
 16  8  2  0  0  0  0
 16 13  1  0  0  0  0
 17  8  1  0  0  0  0
 18 17  2  0  0  0  0
 19 13  2  0  0  0  0
 19 18  1  0  0  0  0
 20 14  1  0  0  0  0
 20 18  1  0  0  0  0
 21 11  1  0  0  0  0
 22 15  1  0  0  0  0
 23 16  1  0  0  0  0
 24 19  1  0  0  0  0
 25 20  2  0  0  0  0
 26  9  1  0  0  0  0
 26 17  1  0  0  0  0
M  END


  Mrv0541 05061309132D          

 26 28  0  0  0  0            999 V2000
   -2.1434    2.0625    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
   -0.7145    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
    0.0000    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
    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
   -1.4289    2.4750    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
    0.7145    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
    0.7145    1.2375    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
    1.4289    2.4750    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
    5.0013    1.2375    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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  2  0  0  0  0
 11  4  1  0  0  0  0
 11  7  2  0  0  0  0
 12  6  1  0  0  0  0
 13  5  1  0  0  0  0
 14  9  2  0  0  0  0
 14 12  1  0  0  0  0
 15  7  1  0  0  0  0
 15 12  2  0  0  0  0
 16  8  2  0  0  0  0
 16 13  1  0  0  0  0
 17  8  1  0  0  0  0
 18 17  2  0  0  0  0
 19 13  2  0  0  0  0
 19 18  1  0  0  0  0
 20 14  1  0  0  0  0
 20 18  1  0  0  0  0
 21 11  1  0  0  0  0
 22 15  1  0  0  0  0
 23 16  1  0  0  0  0
 24 19  1  0  0  0  0
 25 20  2  0  0  0  0
 26  9  1  0  0  0  0
 26 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048547

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H18O6/c1-10(2)3-5-13-16(23)8-17-18(19(13)24)20(25)14(9-26-17)12-6-4-11(21)7-15(12)22/h3-4,6-9,21-24H,5H2,1-2H3

> <INCHI_KEY>
MMPVAPMCVABQPS-UHFFFAOYSA-N

> <FORMULA>
C20H18O6

> <MOLECULAR_WEIGHT>
354.3533

> <EXACT_MASS>
354.110338308

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
37.01200748031911

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.26

> <JCHEM_LOGP>
4.501874067333334

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.418734404828838

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.4136967091951655

> <JCHEM_PKA_STRONGEST_BASIC>
-5.2317685298225465

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
97.90659999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
luteone

> <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      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   6.160   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       2.667   1.540   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      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.336   3.850   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  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3    5   10                                                       
CONECT    4    6   11                                                       
CONECT    5    3   13                                                       
CONECT    6    4   12                                                       
CONECT    7   11   15                                                       
CONECT    8   16   17                                                       
CONECT    9   14   26                                                       
CONECT   10    1    2    3                                                  
CONECT   11    4    7   21                                                  
CONECT   12    6   14   15                                                  
CONECT   13    5   16   19                                                  
CONECT   14    9   12   20                                                  
CONECT   15    7   12   22                                                  
CONECT   16    8   13   23                                                  
CONECT   17    8   18   26                                                  
CONECT   18   17   19   20                                                  
CONECT   19   13   18   24                                                  
CONECT   20   14   18   25                                                  
CONECT   21   11                                                            
CONECT   22   15                                                            
CONECT   23   16                                                            
CONECT   24   19                                                            
CONECT   25   20                                                            
CONECT   26    9   17                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one	ChEBI
3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9ci	HMDB
Luteone?	HMDB
Ruizgenin	HMDB
Ruizgenin, (3beta,5alpha,6alpha,25R)-isomer	MeSH
Ruizgenin, (3beta,5alpha,6alpha,25S)-isomer	MeSH
5 beta-Spirostane-3 beta,6 alpha-diol	MeSH
Ruizgenin, (3beta,5alpha,6beta,25R)-isomer	MeSH

Chemical Formula

C₂₀H₁₈O₆

Average Mass

354.3533 Da

Monoisotopic Mass

354.11034 Da

IUPAC Name

3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one

Traditional Name

luteone

CAS Registry Number

41743-56-0

SMILES

CC(C)=CCC1=C(O)C2=C(OC=C(C2=O)C2=C(O)C=C(O)C=C2)C=C1O

InChI Identifier

InChI=1S/C20H18O6/c1-10(2)3-5-13-16(23)8-17-18(19(13)24)20(25)14(9-26-17)12-6-4-11(21)7-15(12)22/h3-4,6-9,21-24H,5H2,1-2H3

InChI Key

MMPVAPMCVABQPS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Argyrocytisus battandieri	Plant	KNApSAcK
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza uralensis	Plant	KNApSAcK
Hardenbergia violacea	Plant	KNApSAcK
Laburnum anagyroides	Plant	KNApSAcK
Lupinus albus	FooDB	KNAPSACK
Lupinus ananeanus	Plant	KNApSAcK
Lupinus arboreus	Plant	KNApSAcK
Lupinus arcticus	Plant	KNApSAcK
Lupinus elegans	Plant	KNApSAcK
Lupinus luteus	Plant	KNApSAcK
Lupinus mexicanus	Plant	KNApSAcK
Lupinus micranthus	Plant	KNApSAcK
Lupinus pubescens	Plant	KNApSAcK
Lupinus rivularis	Plant	KNApSAcK
Lupinus spp.	Plant	KNApSAcK
Lupinus subcarnosus	Plant	KNApSAcK
Phaseolus lunatus	FooDB	KNAPSACK
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pueraria Phaseoloides	Plant	KNApSAcK
Sophora flavescens	Plant	KNApSAcK
Vandasina retusa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 6-prenylated isoflavanones. These are isoflavanones featuring a C5-isoprenoid unit at the 6-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

6-prenylated isoflavanones

Alternative Parents

Substituents

6-prenylated isoflavanone
Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-hydroxyisoflavones (CHEBI:27917 )
isoflavones (C10498 )
Isoflavonoids (C10498 )
Isoflavonoids (LMPK12050287 )

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	3.26	ALOGPS
logP	4.5	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	6.41	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	97.91 m³·mol⁻¹	ChemAxon
Polarizability	37.01 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

HMDB0036595

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

Luteone_(isoflavone)

METLIN ID

Not Available

PubChem Compound

5281797

PDB ID

Not Available

ChEBI ID

27917

Good Scents ID

Not Available

References

General References

Stobiecki M, Staszkow A, Piasecka A, Garcia-Lopez PM, Zamora-Natera F, Kachlicki P: LC-MSMS profiling of flavonoid conjugates in wild Mexican lupine, Lupinus reflexus. J Nat Prod. 2010 Jul 23;73(7):1254-60. doi: 10.1021/np100139d. [PubMed:20568784 ]

Showing NP-Card for Luteone (NP0048547)

MOL for NP0048547 (Luteone)

3D MOL for NP0048547 (Luteone)

3D SDF for NP0048547 (Luteone)

3D-SDF for NP0048547 (Luteone)

PDB for NP0048547 (Luteone)

3D PDB for NP0048547 (Luteone)

SMILES for NP0048547 (Luteone)

INCHI for NP0048547 (Luteone)

Structure for NP0048547 (Luteone)

3D Structure for NP0048547 (Luteone)