NP-MRD: Showing NP-Card for 2'-Hydroxyformononetin (NP0050243)

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Record Information

Version

2.0

Created at

2022-04-27 20:49:38 UTC

Updated at

2022-04-27 20:49:38 UTC

NP-MRD ID

NP0050243

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2'-Hydroxyformononetin

Description

Xenognosin B belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone. Thus, xenognosin b is considered to be a flavonoid lipid molecule. Xenognosin B is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Xenognosin B exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Xenognosin B has been detected, but not quantified in, several different foods, such as chinese chives, chanterelles, rapes, chicory leaves, and sweet marjorams. 2'-Hydroxyformononetin is found in Agalinis purpurea, Dalbergia odorifera , Dalbergia sissoo, Euchresta formosana, Glycyrrhiza pallidiflora, Millettia brandisiana, Pycnanthus angolensis , Trifolium repens , Virola cadudifolia and Virola multinervia. 2'-Hydroxyformononetin was first documented in 1990 (PMID: 2306102). This could make xenognosin b a potential biomarker for the consumption of these foods (PMID: 9790908) (PMID: 1912490) (PMID: 1915347) (PMID: 9525107).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306052D          

 21 23  0  0  0  0            999 V2000
    7.1447    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
    1.4289    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
    1.4289    0.8250    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
    3.5724    1.2375    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
    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
    2.1434    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
    2.1434    1.2375    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
    0.0000    0.8250    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
    2.8579    3.3000    0.0000 O   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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  9  2  1  0  0  0  0
  9  6  2  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 12  4  1  0  0  0  0
 13  8  2  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  2  0  0  0  0
 15  6  1  0  0  0  0
 15 12  2  0  0  0  0
 16 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17  9  1  0  0  0  0
 18 14  1  0  0  0  0
 19 16  2  0  0  0  0
 20  1  1  0  0  0  0
 20 10  1  0  0  0  0
 21  8  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050243

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-20-10-3-5-11(14(18)7-10)13-8-21-15-6-9(17)2-4-12(15)16(13)19/h2-8,17-18H,1H3

> <INCHI_KEY>
XKHHKXCBFHUOHM-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.2635

> <EXACT_MASS>
284.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
28.733494299555378

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.35

> <JCHEM_LOGP>
2.5727664456666663

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.591281529614783

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.469800939597965

> <JCHEM_PKA_STRONGEST_BASIC>
-4.721321174350647

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
76.1652

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.44e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2'-hydroxyformononetin

> <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      13.337   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   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       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    4    9                                                       
CONECT    3    5   10                                                       
CONECT    4    2   12                                                       
CONECT    5    3   11                                                       
CONECT    6    9   15                                                       
CONECT    7   10   14                                                       
CONECT    8   13   21                                                       
CONECT    9    2    6   17                                                  
CONECT   10    3    7   20                                                  
CONECT   11    5   13   14                                                  
CONECT   12    4   15   16                                                  
CONECT   13    8   11   16                                                  
CONECT   14    7   11   18                                                  
CONECT   15    6   12   21                                                  
CONECT   16   12   13   19                                                  
CONECT   17    9                                                            
CONECT   18   14                                                            
CONECT   19   16                                                            
CONECT   20    1   10                                                       
CONECT   21    8   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
2'-Hydroformononetin	ChEBI
2',7-Dihydroxy-4'-methoxyisoflavone	HMDB
2-HYDROXYFORMONONETIN	HMDB
7,2'-Dihydroxy-4'-methoxyisoflavone	HMDB
7-Hydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-chromen-4-one	HMDB
Xenognosin b	ChEBI

Chemical Formula

C₁₆H₁₂O₅

Average Mass

284.2635 Da

Monoisotopic Mass

284.06847 Da

IUPAC Name

7-hydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

2'-hydroxyformononetin

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O

InChI Identifier

InChI=1S/C16H12O5/c1-20-10-3-5-11(14(18)7-10)13-8-21-15-6-9(17)2-4-12(15)16(13)19/h2-8,17-18H,1H3

InChI Key

XKHHKXCBFHUOHM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agalinis purpurea	Plant	KNApSAcK
Dalbergia odorifera	Plant	KNApSAcK
Dalbergia sissoo	LOTUS Database	35616633
Euchresta formosana	LOTUS Database	35616633
Glycyrrhiza pallidiflora	Plant	KNApSAcK
Millettia brandisiana	LOTUS Database	35616633
Pycnanthus angolensis	Animalia	KNApSAcK
Trifolium repens	Plant	KNApSAcK
Virola cadudifolia	Plant	KNApSAcK
Virola multinervia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

4'-O-methylisoflavones

Alternative Parents

Substituents

4p-o-methylisoflavone
Isoflavone
Hydroxyisoflavonoid
Chromone
Methoxyphenol
1-benzopyran
Benzopyran
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Pyran
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxyisoflavone (CHEBI:17678 )
7-hydroxyisoflavones (CHEBI:17678 )
isoflavones (C02920 )
Isoflavonoids (LMPK12050081 )
a small molecule (2-HYDROXYFORMONONETIN )

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	3.35	ALOGPS
logP	2.57	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.47	ChemAxon
pKa (Strongest Basic)	-4.7	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	2	ChemAxon
Refractivity	76.17 m³·mol⁻¹	ChemAxon
Polarizability	28.73 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

HMDB0031720

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

2-HYDROXYFORMONONETIN

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280551

PDB ID

Not Available

ChEBI ID

17678

Good Scents ID

Not Available

References

General References

Fischer D, Ebenau-Jehle C, Grisebach H: Phytoalexin synthesis in soybean: purification and characterization of NADPH:2'-hydroxydaidzein oxidoreductase from elicitor-challenged soybean cell cultures. Arch Biochem Biophys. 1990 Feb 1;276(2):390-5. doi: 10.1016/0003-9861(90)90737-j. [PubMed:2306102 ]
Akashi T, Aoki T, Ayabe S: CYP81E1, a cytochrome P450 cDNA of licorice (Glycyrrhiza echinata L.), encodes isoflavone 2'-hydroxylase. Biochem Biophys Res Commun. 1998 Oct 9;251(1):67-70. doi: 10.1006/bbrc.1998.9414. [PubMed:9790908 ]
Paiva NL, Edwards R, Sun YJ, Hrazdina G, Dixon RA: Stress responses in alfalfa (Medicago sativa L.) 11. Molecular cloning and expression of alfalfa isoflavone reductase, a key enzyme of isoflavonoid phytoalexin biosynthesis. Plant Mol Biol. 1991 Oct;17(4):653-67. doi: 10.1007/BF00037051. [PubMed:1912490 ]
Tiemann K, Inze D, Van Montagu M, Barz W: Pterocarpan phytoalexin biosynthesis in elicitor-challenged chickpea (Cicer arietinum L.) cell cultures. Purification, characterization and cDNA cloning of NADPH:isoflavone oxidoreductase. Eur J Biochem. 1991 Sep 15;200(3):751-7. doi: 10.1111/j.1432-1033.1991.tb16241.x. [PubMed:1915347 ]
Chan SC, Chang YS, Wang JP, Chen SC, Kuo SC: Three new flavonoids and antiallergic, anti-inflammatory constituents from the heartwood of Dalbergia odorifera. Planta Med. 1998 Mar;64(2):153-8. doi: 10.1055/s-2006-957394. [PubMed:9525107 ]

Showing NP-Card for 2'-Hydroxyformononetin (NP0050243)

MOL for NP0050243 (2'-Hydroxyformononetin)

3D MOL for NP0050243 (2'-Hydroxyformononetin)

3D SDF for NP0050243 (2'-Hydroxyformononetin)

3D-SDF for NP0050243 (2'-Hydroxyformononetin)

PDB for NP0050243 (2'-Hydroxyformononetin)

3D PDB for NP0050243 (2'-Hydroxyformononetin)

SMILES for NP0050243 (2'-Hydroxyformononetin)

INCHI for NP0050243 (2'-Hydroxyformononetin)

Structure for NP0050243 (2'-Hydroxyformononetin)

3D Structure for NP0050243 (2'-Hydroxyformononetin)