NP-MRD: Showing NP-Card for Phaseollin isoflavone (NP0046914)

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Record Information

Version

2.0

Created at

2022-03-17 20:31:37 UTC

Updated at

2022-03-17 20:31:37 UTC

NP-MRD ID

NP0046914

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phaseollin isoflavone

Description

Glabrone, also known as eurycarpin b, belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton. Thus, glabrone is considered to be a flavonoid lipid molecule. Glabrone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Glabrone has been detected, but not quantified in, herbs and spices and tea. Phaseollin isoflavone is found in Euphorbia helioscopia L. , Glycyrrhiza eurycarpa, Glycyrrhiza glabra , Glycyrrhiza inflata and Glycyrrhiza uralensis . This could make glabrone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212542D          

 25 28  0  0  0  0            999 V2000
   -3.3000    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000   -1.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711   -1.5616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429    1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2723   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9573    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9573    2.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429    2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    1.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0843    2.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687    1.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1604    1.3193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7289   -1.5616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    0.9134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 18 12  1  0  0  0  0
 12 16  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  2  0  0  0  0
 17 20  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 13 23  1  0  0  0  0
  3 24  1  0  0  0  0
  7 25  2  0  0  0  0
M  END


  Mrv0541 02241212542D          

 25 28  0  0  0  0            999 V2000
   -3.3000    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0145   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3000   -1.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711   -1.5616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429    1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4421    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2723   -0.3241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9868    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9573    0.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9573    2.5635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429    2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    1.3259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718    2.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0843    2.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687    1.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1604    1.3193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7289   -1.5616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8711    0.9134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 18 12  1  0  0  0  0
 12 16  2  0  0  0  0
 16 19  1  0  0  0  0
 17 18  2  0  0  0  0
 17 20  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 13 23  1  0  0  0  0
  3 24  1  0  0  0  0
  7 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046914

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC2=C(C=C1)C(O)=C(C=C2)C1=COC2=C(C=CC(O)=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O5/c1-20(2)8-7-14-16(25-20)6-5-12(18(14)22)15-10-24-17-9-11(21)3-4-13(17)19(15)23/h3-10,21-22H,1-2H3

> <INCHI_KEY>
COLMVFWKLOZOOP-UHFFFAOYSA-N

> <FORMULA>
C20H16O5

> <MOLECULAR_WEIGHT>
336.338

> <EXACT_MASS>
336.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
35.433219152869

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-3-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-4H-chromen-4-one

> <ALOGPS_LOGP>
4.37

> <JCHEM_LOGP>
3.631061113333333

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.53014404611579

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.4691863068941595

> <JCHEM_PKA_STRONGEST_BASIC>
-4.778411389526237

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
94.0954

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
glabrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.160   0.165   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.494  -0.605   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.494  -2.145   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.160  -2.915   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.826  -2.145   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.826  -0.605   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.493   0.165   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.493  -2.915   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.159  -2.145   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.159  -0.605   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.825   0.165   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.453   2.475   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.825   1.705   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.508  -0.605   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.842   0.165   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.787   1.705   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.787   4.785   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.453   4.015   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.121   2.475   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.121   4.015   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.891   5.349   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.608   3.616   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.166   2.463   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -8.827  -2.915   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -3.493   1.705   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10   25                                                  
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   18   16                                                  
CONECT   13   11   12   23                                                  
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12   19                                                  
CONECT   17   18   20                                                       
CONECT   18   12   17                                                       
CONECT   19   16   20                                                       
CONECT   20   17   19   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   13                                                            
CONECT   24    3                                                            
CONECT   25    7                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
7-Hydroxy-3-(5-hydroxy-2,2-dimethyl-2H-1-benzopyran-6-yl)-4H-1-benzopyran-4-one, 9ci	HMDB
Eurycarpin b	HMDB
Morusin hydroperoxide	HMDB
7,2'-Dihydroxy-6'',6''-dimethylpyrano-(2'',3''-4',3')isoflavone	MeSH

Chemical Formula

C₂₀H₁₆O₅

Average Mass

336.3380 Da

Monoisotopic Mass

336.09977 Da

IUPAC Name

7-hydroxy-3-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-4H-chromen-4-one

Traditional Name

glabrone

CAS Registry Number

Not Available

SMILES

CC1(C)OC2=C(C=C1)C(O)=C(C=C2)C1=COC2=C(C=CC(O)=C2)C1=O

InChI Identifier

InChI=1S/C20H16O5/c1-20(2)8-7-14-16(25-20)6-5-12(18(14)22)15-10-24-17-9-11(21)3-4-13(17)19(15)23/h3-10,21-22H,1-2H3

InChI Key

COLMVFWKLOZOOP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Euphorbia helioscopia	Plant	KNApSAcK
Glycyrrhiza eurycarpa	Plant	KNApSAcK
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza inflata	Plant	KNApSAcK
Glycyrrhiza uralensis	Plant	KNApSAcK
Phaseolus coccineus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Phaseolus vulgaris	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Pyranoisoflavonoids

Direct Parent

Pyranoisoflavonoids

Alternative Parents

Substituents

Pyranoisoflavonoid
Isoflavone
Hydroxyisoflavonoid
2,2-dimethyl-1-benzopyran
Chromone
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyran
Heteroaromatic compound
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050074 )

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	4.37	ALOGPS
logP	3.63	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	6.47	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	94.1 m³·mol⁻¹	ChemAxon
Polarizability	35.43 Å³	ChemAxon
Number of Rings	4	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

HMDB0029533

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000674

KNApSAcK ID

C00009434

Chemspider ID

4476468

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317652

PDB ID

Not Available

ChEBI ID

698651

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Phaseollin isoflavone (NP0046914)

MOL for NP0046914 (Phaseollin isoflavone)

3D MOL for NP0046914 (Phaseollin isoflavone)

3D SDF for NP0046914 (Phaseollin isoflavone)

3D-SDF for NP0046914 (Phaseollin isoflavone)

PDB for NP0046914 (Phaseollin isoflavone)

3D PDB for NP0046914 (Phaseollin isoflavone)

SMILES for NP0046914 (Phaseollin isoflavone)

INCHI for NP0046914 (Phaseollin isoflavone)

Structure for NP0046914 (Phaseollin isoflavone)

3D Structure for NP0046914 (Phaseollin isoflavone)