NP-MRD: Showing NP-Card for Licoisoflavone A (NP0047861)

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Record Information

Version

2.0

Created at

2022-03-17 20:47:09 UTC

Updated at

2022-03-17 20:47:10 UTC

NP-MRD ID

NP0047861

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Licoisoflavone A

Description

Licoisoflavone A, also known as phaseoluteone, belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, licoisoflavone a is considered to be a flavonoid lipid molecule. Licoisoflavone A is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Licoisoflavone A has been detected, but not quantified in, several different foods, such as oriental wheats, green beans, ryes, common wheats, and barley. Licoisoflavone A is found in Echinosophora koreensis, Glycyrrhiza aspera, Glycyrrhiza glabra , Glycyrrhiza inflata , Glycyrrhiza uralensis , Hardenbergia violacea, Lupinus angustifolius , Sophora moorcroftiana and Vandasina retusa. Licoisoflavone A was first documented in 1997 (PMID: 11499034). This could make licoisoflavone a a potential biomarker for the consumption of these foods (PMID: 11783953) (PMID: 23074904).

Structure

MOL SDF PDB SMILES InChI

Licoisoflavone A
  Mrv1572001071617322D          

 26 28  0  0  0  0            999 V2000
   -0.7029   -0.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117   -0.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4208   -0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6994    0.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7260   -0.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0048   -1.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1354   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4243   -1.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    0.8265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4407   -0.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7260    0.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7192   -2.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1319    0.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8395   -0.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4372   -1.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1551   -0.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8395    0.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5574   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8395   -1.6468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1483   -2.0796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8662   -0.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5574    0.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5841   -0.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2719    0.8299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2986   -0.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875    0.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  2  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 13  2  0  0  0  0
  7 14  1  0  0  0  0
  9 13  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  0  0  0  0
 12 15  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 14 19  1  0  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 17 22  2  0  0  0  0
 18 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
M  END

Licoisoflavone A
  Mrv1572001071617322D          

 26 28  0  0  0  0            999 V2000
   -0.7029   -0.4170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117   -0.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4208   -0.8258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6994    0.4074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7260   -0.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0048   -1.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1354   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4243   -1.6501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    0.8265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4407   -0.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7260    0.4039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7192   -2.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1319    0.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8395   -0.8224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4372   -1.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1551   -0.4274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8395    0.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5574   -0.4101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8395   -1.6468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1483   -2.0796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8662   -0.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5574    0.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5841   -0.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2719    0.8299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2986   -0.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5875    0.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  5 10  2  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7 13  2  0  0  0  0
  7 14  1  0  0  0  0
  9 13  1  0  0  0  0
 10 15  1  0  0  0  0
 10 16  1  0  0  0  0
 12 15  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  2  0  0  0  0
 14 19  1  0  0  0  0
 15 20  1  0  0  0  0
 16 21  1  0  0  0  0
 17 22  2  0  0  0  0
 18 22  1  0  0  0  0
 21 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047861

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC1=C(O)C(=CC=C1O)C1=COC2=C(C(O)=CC(O)=C2)C1=O

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

> <INCHI_KEY>
KCUZCRLRQVRBBV-UHFFFAOYSA-N

> <FORMULA>
C20H18O6

> <MOLECULAR_WEIGHT>
354.358

> <EXACT_MASS>
354.1103383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
36.82973207927273

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.29

> <JCHEM_LOGP>
4.501874067333334

> <ALOGPS_LOGS>
-4.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.933502740524942

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.535585812393612

> <JCHEM_PKA_STRONGEST_BASIC>
-5.347046407487893

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
97.90659999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
licoisoflavone A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Licoisoflavone A                                  
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      -1.312  -0.778   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.022  -1.554   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.652  -1.541   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.306   0.760   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.355  -0.791   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.009  -3.093   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.986  -0.766   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.659  -3.080   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.639   1.543   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.689  -1.561   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.355   0.754   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.343  -3.875   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.980   0.773   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.300  -1.535   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.683  -3.106   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.023  -0.798   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.300   1.549   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.640  -0.766   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -5.300  -3.074   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.010  -3.882   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.350  -1.573   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.640   0.773   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.690  -0.810   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -7.974   1.549   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.024  -1.586   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.697   0.728   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   13   14                                                  
CONECT    8    3                                                            
CONECT    9    4   13                                                       
CONECT   10    5   15   16                                                  
CONECT   11    5                                                            
CONECT   12    6   15                                                       
CONECT   13    7    9   17                                                  
CONECT   14    7   18   19                                                  
CONECT   15   10   12   20                                                  
CONECT   16   10   21                                                       
CONECT   17   13   22                                                       
CONECT   18   14   22                                                       
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   16   23                                                       
CONECT   22   17   18   24                                                  
CONECT   23   21   25   26                                                  
CONECT   24   22                                                            
CONECT   25   23                                                            
CONECT   26   23                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
2',4',5,7-Tetrahydroxy-3'-(3,3-dimethylallyl)isoflavone	ChEBI
Phaseoluteone	ChEBI
3'-Isopentenyl-2',4',5,7-tetrahydroxyisoflavone	HMDB
Licoisoflavone	HMDB
[2,4-Dihydroxy-3-(3-methyl-2-butenyl)phenyl]-5,7-dihydroxy-4H-1-benzopyran-4-one, 9ci	HMDB

Chemical Formula

C₂₀H₁₈O₆

Average Mass

354.3580 Da

Monoisotopic Mass

354.11034 Da

IUPAC Name

3-[2,4-dihydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-5,7-dihydroxy-4H-chromen-4-one

Traditional Name

licoisoflavone A

CAS Registry Number

66056-19-7

SMILES

CC(C)=CCC1=C(O)C(=CC=C1O)C1=COC2=C(C(O)=CC(O)=C2)C1=O

InChI Identifier

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

InChI Key

KCUZCRLRQVRBBV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Echinosophora koreensis	Plant	KNApSAcK
Glycyrrhiza aspera	Plant	KNApSAcK
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza inflata	Plant	KNApSAcK
Glycyrrhiza uralensis	Plant	KNApSAcK
Hardenbergia violacea	Plant	KNApSAcK
Lupinus albus	FooDB	KNAPSACK
Lupinus angustifolius	Plant	KNApSAcK
Phaseolus coccineus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sophora moorcroftiana	Plant	KNApSAcK
Vandasina retusa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-hydroxyisoflavones (CHEBI:28620 )
isoflavones (C10486 )
Isoflavonoids (C10486 )
Isoflavonoids (LMPK12050286 )

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	3.29	ALOGPS
logP	4.5	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	6.54	ChemAxon
pKa (Strongest Basic)	-5.3	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	36.83 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

HMDB0034125

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

5281789

PDB ID

Not Available

ChEBI ID

28620

Good Scents ID

Not Available

References

General References

Zhang YM, Xu XD, Hu BH, Liu Q, Hou CY, Liu YL, Yang JS: [Isoflavones from Glycyrrhiza eurycarpa]. Yao Xue Xue Bao. 1997 Apr;32(4):301-4. [PubMed:11499034 ]
Bobrowska-Hagerstrand M, Wrobel A, Rychlik B, Bartosz G, Soderstrom T, Shirataki Y, Motohashi N, Molnar J, Michalak K, Hagerstrand H: Monitoring of MRP-like activity in human erythrocytes: inhibitory effect of isoflavones. Blood Cells Mol Dis. 2001 Sep-Oct;27(5):894-900. doi: 10.1006/bcmd.2001.0459. [PubMed:11783953 ]
Quesada L, Areche C, Astudillo L, Gutierrez M, Sepulveda B, San-Martin A: Biological activity of isoflavonoids from Azorella madreporica. Nat Prod Commun. 2012 Sep;7(9):1187-8. [PubMed:23074904 ]

Showing NP-Card for Licoisoflavone A (NP0047861)

MOL for NP0047861 (Licoisoflavone A)

3D MOL for NP0047861 (Licoisoflavone A)

3D SDF for NP0047861 (Licoisoflavone A)

3D-SDF for NP0047861 (Licoisoflavone A)

PDB for NP0047861 (Licoisoflavone A)

3D PDB for NP0047861 (Licoisoflavone A)

SMILES for NP0047861 (Licoisoflavone A)

INCHI for NP0047861 (Licoisoflavone A)

Structure for NP0047861 (Licoisoflavone A)

3D Structure for NP0047861 (Licoisoflavone A)