NP-MRD: Showing NP-Card for Persicogenin (NP0048810)

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Record Information

Version

2.0

Created at

2022-03-17 21:02:32 UTC

Updated at

2022-03-17 21:02:32 UTC

NP-MRD ID

NP0048810

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Persicogenin

Description

3',5-Dihydroxy-4',7-dimethoxyflavanone, also known as persicogenin, belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, 3',5-dihydroxy-4',7-dimethoxyflavanone is considered to be a flavonoid lipid molecule. 3',5-Dihydroxy-4',7-dimethoxyflavanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 3',5-Dihydroxy-4',7-dimethoxyflavanone has been detected, but not quantified in, peachs. Persicogenin is found in Adenothamnus validus, Artemisia campestris, Chromolaena odorata, Eriodictyon californicum, Heliotropium glutinosum and Salvia miltiorrhiza . This could make 3',5-dihydroxy-4',7-dimethoxyflavanone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309482D          

 23 25  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  9  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  4  1  0  0  0  0
 14 11  2  0  0  0  0
 15  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16  7  2  0  0  0  0
 17 12  2  0  0  0  0
 17 13  1  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  2  0  0  0  0
 21  1  1  0  0  0  0
 21 10  1  0  0  0  0
 22  2  1  0  0  0  0
 22 14  1  0  0  0  0
 23 15  1  0  0  0  0
 23 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048810

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC(O)=C(OC)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O6/c1-21-10-6-12(19)17-13(20)8-15(23-16(17)7-10)9-3-4-14(22-2)11(18)5-9/h3-7,15,18-19H,8H2,1-2H3

> <INCHI_KEY>
LWBHKKLWSUFUNZ-UHFFFAOYSA-N

> <FORMULA>
C17H16O6

> <MOLECULAR_WEIGHT>
316.3053

> <EXACT_MASS>
316.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
32.36443517914872

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.80

> <JCHEM_LOGP>
2.8233308406666655

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.145853412099019

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.538408957079664

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9124889258484368

> <JCHEM_POLAR_SURFACE_AREA>
85.22000000000001

> <JCHEM_REFRACTIVITY>
82.23530000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
persicogenin

> <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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.671  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   0.000   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       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3    4    9                                                       
CONECT    4    3   14                                                       
CONECT    5    9   11                                                       
CONECT    6   10   12                                                       
CONECT    7   10   16                                                       
CONECT    8   13   15                                                       
CONECT    9    3    5   15                                                  
CONECT   10    6    7   21                                                  
CONECT   11    5   14   18                                                  
CONECT   12    6   17   19                                                  
CONECT   13    8   17   20                                                  
CONECT   14    4   11   22                                                  
CONECT   15    8    9   23                                                  
CONECT   16    7   17   23                                                  
CONECT   17   12   13   16                                                  
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21    1   10                                                       
CONECT   22    2   14                                                       
CONECT   23   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
Persicogenin	HMDB

Chemical Formula

C₁₇H₁₆O₆

Average Mass

316.3053 Da

Monoisotopic Mass

316.09469 Da

IUPAC Name

5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

persicogenin

CAS Registry Number

28590-40-1

SMILES

COC1=CC(O)=C2C(=O)CC(OC2=C1)C1=CC(O)=C(OC)C=C1

InChI Identifier

InChI=1S/C17H16O6/c1-21-10-6-12(19)17-13(20)8-15(23-16(17)7-10)9-3-4-14(22-2)11(18)5-9/h3-7,15,18-19H,8H2,1-2H3

InChI Key

LWBHKKLWSUFUNZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Adenothamnus validus	LOTUS Database	35616633
Artemisia campestris	LOTUS Database	35616633
Chromolaena odorata	LOTUS Database	35616633
Eriodictyon californicum	LOTUS Database	35616633
Heliotropium glutinosum	LOTUS Database	35616633
Prunus persica	FooDB	KNAPSACK
Salvia miltiorrhiza	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

7-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
Flavanone
Hydroxyflavonoid
5-hydroxyflavonoid
3'-hydroxyflavonoid
Flavan
Chromone
Chromane
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Methoxybenzene
Aryl alkyl ketone
Anisole
Phenol ether
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavanones (LMPK12140588 )

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	2.8	ALOGPS
logP	2.82	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.54	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	82.24 m³·mol⁻¹	ChemAxon
Polarizability	32.36 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

HMDB0037481

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016552

KNApSAcK ID

C00008300

Chemspider ID

283330

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

320054

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Persicogenin (NP0048810)

MOL for NP0048810 (Persicogenin)

3D MOL for NP0048810 (Persicogenin)

3D SDF for NP0048810 (Persicogenin)

3D-SDF for NP0048810 (Persicogenin)

PDB for NP0048810 (Persicogenin)

3D PDB for NP0048810 (Persicogenin)

SMILES for NP0048810 (Persicogenin)

INCHI for NP0048810 (Persicogenin)

Structure for NP0048810 (Persicogenin)

3D Structure for NP0048810 (Persicogenin)