NP-MRD: Showing NP-Card for 2'-Methylisoliquiritigenin (NP0048723)

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Record Information

Version

2.0

Created at

2022-03-17 21:01:10 UTC

Updated at

2022-03-17 21:01:10 UTC

NP-MRD ID

NP0048723

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2'-Methylisoliquiritigenin

Description

3-(4-Hydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)-2-propen-1-one, also known as 4,4'-dihydroxy-2'-methoxychalcone or isoliquiritigenin 2'-methy ether, belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups. Thus, 3-(4-hydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)-2-propen-1-one is considered to be a flavonoid lipid molecule. 3-(4-Hydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)-2-propen-1-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 3-(4-Hydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)-2-propen-1-one has been detected, but not quantified in, common pea and pulses. 2'-Methylisoliquiritigenin is found in Alpinia japonica, Amorpha fruticosa, Anemarrhena asphodeloides, Bauhinia guianensis , Bauhinia manca, Caesalpinia sappan , Broussonetia papyrifera , Calicotome villosa, Dalbergia odorifera , Dracaena cambodiana, Dracaena cinnabari, Dracaena cochinchinensis, Dracaena draco , Entada phaseoloides, Glycyrrhiza uralensis, Pithecellobium unguis-cati and Soymida febrifuga. This could make 3-(4-hydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)-2-propen-1-one a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv1652304072023402D          

 20 21  0  0  0  0            999 V2000
 9999.308910000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.0234 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.308910001.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.738110000.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.880010001.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.4511 9998.7624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.5988 9998.7624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.880010000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.165610000.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.1656 9999.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8800 9998.7627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5945 9999.1752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.594510000.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.883310000.0003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.168910000.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.454310000.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4543 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1687 9998.7628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.8833 9999.1753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.165610001.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  2  4  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
  1 13  1  0  0  0  0
  8  5  1  0  0  0  0
 10  6  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 14  1  0  0  0  0
  4 16  1  0  0  0  0
 19  7  1  0  0  0  0
  5 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048723

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=CC=C1C(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O4/c1-20-16-10-13(18)7-8-14(16)15(19)9-4-11-2-5-12(17)6-3-11/h2-10,17-18H,1H3/b9-4+

> <INCHI_KEY>
PACBGANPVNHGNP-RUDMXATFSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.28

> <EXACT_MASS>
270.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
28.642672720828052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(4-hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
3.1255233999999996

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.067578960400153

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.89416895889298

> <JCHEM_PKA_STRONGEST_BASIC>
-4.885442490286645

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
77.30199999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-deoxysappanchalcone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-APR-20         0                                  
HETATM    1  C   UNK     0    8665.3778667.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.7108666.666   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8665.3778668.977   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8668.0448667.437   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8662.7098668.977   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8660.0428664.356   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8673.3848664.356   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8662.7098667.437   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.3768666.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8661.3768665.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.7098664.357   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.0438665.127   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8664.0438666.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8672.0498666.667   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8670.7158667.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8669.3818666.667   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8669.3818665.127   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8670.7158664.357   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8672.0498665.127   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8661.3768669.747   0.000  0.00  0.00           C+0
CONECT    1    2    3   13                                                  
CONECT    2    1    4                                                       
CONECT    3    1                                                            
CONECT    4    2   16                                                       
CONECT    5    8   20                                                       
CONECT    6   10                                                            
CONECT    7   19                                                            
CONECT    8    9   13    5                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11    6                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8    1                                                  
CONECT   14   15   19                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17    4                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14    7                                                  
CONECT   20    5                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
4,4'-Dihydroxy-2'-methoxychalcone	ChEBI
Isoliquiritigenin 2'-methy ether	HMDB
3-Deoxysappanchalcone	HMDB
(2E)-1-(4-Hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one	HMDB
1-(4-Hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one	HMDB
2'-Methoxyisoliquiritigenin	HMDB
2'-Methylisoliquiritigenin	HMDB
2'-O-Methylisoliquiritigenin	HMDB
2’-Methoxyisoliquiritigenin	HMDB
2’-Methylisoliquiritigenin	HMDB
2’-O-Methylisoliquiritigenin	HMDB
3-(4-Hydroxyphenyl)-1-(4-hydroxy-2-methoxyphenyl)-2-propen-1-one	HMDB
4,4’-Dihydroxy-2’-methoxychalcone	HMDB
Isoliquiritigenin 2'-methyl ether	HMDB
Isoliquiritigenin 2’-methyl ether	HMDB

Chemical Formula

C₁₆H₁₄O₄

Average Mass

270.2800 Da

Monoisotopic Mass

270.08921 Da

IUPAC Name

(2E)-1-(4-hydroxy-2-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

3-deoxysappanchalcone

CAS Registry Number

51828-10-5

SMILES

COC1=CC(O)=CC=C1C(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C16H14O4/c1-20-16-10-13(18)7-8-14(16)15(19)9-4-11-2-5-12(17)6-3-11/h2-10,17-18H,1H3/b9-4+

InChI Key

PACBGANPVNHGNP-RUDMXATFSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Alpinia japonica	LOTUS Database	35616633
Amorpha fruticosa	LOTUS Database	35616633
Anemarrhena asphodeloides	LOTUS Database	35616633
Bauhinia guianensis	Plant	KNApSAcK
Bauhinia manca	Plant	KNApSAcK
Biancaea sappan	Plant	KNApSAcK
Broussonetia papyrifera	Plant	KNApSAcK
Calicotome villosa	LOTUS Database	35616633
Dalbergia odorifera	Plant	KNApSAcK
Dracaena cambodiana	LOTUS Database	35616633
Dracaena cinnabari	LOTUS Database	35616633
Dracaena cochinchinensis	Plant	KNApSAcK
Dracaena draco	Plant	KNApSAcK
Entada phaseoloides	LOTUS Database	35616633
Glycyrrhiza uralensis	LOTUS Database	35616633
Pisum sativum	FooDB	KNAPSACK
Pithecellobium unguis-cati	Plant	KNApSAcK
Soymida febrifuga	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Cinnamylphenols

Direct Parent

Cinnamylphenols

Alternative Parents

Substituents

Cinnamylphenol
Hydroxycinnamic acid or derivatives
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Benzoyl
Aryl ketone
Styrene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Alpha,beta-unsaturated ketone
Enone
Ketone
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:519567 )
monomethoxybenzene (CHEBI:519567 )
chalcones (CHEBI:519567 )
chalcones (C15531 )
Chalcones and dihydrochalcones (LMPK12120098 )

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	3.4	ALOGPS
logP	3.13	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	7.89	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.3 m³·mol⁻¹	ChemAxon
Polarizability	28.64 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon