NP-MRD: Showing NP-Card for Geraldone (NP0047763)

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Record Information

Version

2.0

Created at

2022-03-17 20:45:34 UTC

Updated at

2022-03-17 20:45:34 UTC

NP-MRD ID

NP0047763

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Geraldone

Description

7-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one, also known as 5-deoxychrysoeriol or 7,4'-dihydroxy-3'-methoxyflavone, belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone. Thus, 7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one is considered to be a flavonoid lipid molecule. 7-Hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one is found, on average, in the highest concentration within broad beans. This could make 7-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-chromen-4-one a potential biomarker for the consumption of these foods. Geraldone is found in Albizia julibrissin, Salvertia convallariodora, Scutellaria baicalensis, Tephrosia pumila , Trifolium repens , Trifolium subterraneum and Vochysia einnamonea. Geraldone was first documented in 2004 (PMID: 15283458). A dihydroxyflavone that is the 5-deoxy-derivative of 4',5,7-trihydroxy-3'-methoxyflavone (chrysoeriol) (PMID: 24886138).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309171723232D          

 21 23  0  0  0  0            999 V2000
    7.8592   -0.4125    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
    1.4289    0.8250    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
    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
    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
    2.8579    0.8250    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
    3.5724    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
    6.4302   -0.4125    0.0000 C   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    2.0625    0.0000 O   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
    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
  5  2  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  4  1  0  0  0  0
 12  5  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  2  0  0  0  0
 16  6  1  0  0  0  0
 16 12  2  0  0  0  0
 17 10  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
 20  1  1  0  0  0  0
 20 16  1  0  0  0  0
 21 14  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047763

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2

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

> <INCHI_KEY>
OUMMPAFEQHTYIZ-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.2635

> <EXACT_MASS>
284.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.877858246940267

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
2.202583189666666

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.201340904712877

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.505062139526472

> <JCHEM_PKA_STRONGEST_BASIC>
-4.771655119483572

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
77.39620000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
geraldone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-SEP-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-SEP-17         0                                  
HETATM    1  C   UNK     0      14.670  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669  -0.000   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       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.003  -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       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    5    9                                                       
CONECT    3    4   10                                                       
CONECT    4    3   11                                                       
CONECT    5    2   12                                                       
CONECT    6    9   16                                                       
CONECT    7   10   15                                                       
CONECT    8   13   14                                                       
CONECT    9    2    6   14                                                  
CONECT   10    3    7   17                                                  
CONECT   11    4   13   15                                                  
CONECT   12    5   16   18                                                  
CONECT   13    8   11   19                                                  
CONECT   14    8    9   21                                                  
CONECT   15    7   11   21                                                  
CONECT   16    6   12   20                                                  
CONECT   17   10                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20    1   16                                                       
CONECT   21   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
5-Deoxychrysoeriol	ChEBI
7,4'-Dihydroxy-3'-methoxyflavone	ChEBI

Chemical Formula

C₁₆H₁₂O₅

Average Mass

284.2635 Da

Monoisotopic Mass

284.06847 Da

IUPAC Name

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

Traditional Name

geraldone

CAS Registry Number

21583-32-4

SMILES

COC1=C(O)C=CC(=C1)C1=CC(=O)C2=C(O1)C=C(O)C=C2

InChI Identifier

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

InChI Key

OUMMPAFEQHTYIZ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Albizia julibrissin	LOTUS Database	35616633
Salvertia convallariodora	Plant	KNApSAcK
Scutellaria baicalensis	LOTUS Database	35616633
Tephrosia pumila	Plant	KNApSAcK
Trifolium repens	Plant	KNApSAcK
Trifolium subterraneum	Plant	KNApSAcK
Vicia faba	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vochysia einnamonea	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3'-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C3' atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

3'-O-methylated flavonoids

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
Methoxyphenol
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:5326 )
monomethoxyflavone (CHEBI:5326 )
flavones (C10047 )
Flavones and Flavonols (C10047 )
Flavones and Flavonols (LMPK12110043 )

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	3.37	ALOGPS
logP	2.2	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.51	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	2	ChemAxon
Refractivity	77.4 m³·mol⁻¹	ChemAxon
Polarizability	28.88 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

HMDB0133330

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012022

KNApSAcK ID

C00003826

Chemspider ID

Not Available

KEGG Compound ID

C10047

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281618

PDB ID

Not Available

ChEBI ID

5326

Good Scents ID

Not Available

References

General References

Jung MJ, Kang SS, Jung HA, Kim GJ, Choi JS: Isolation of flavonoids and a cerebroside from the stem bark of Albizzia julibrissin. Arch Pharm Res. 2004 Jun;27(6):593-9. doi: 10.1007/BF02980155. [PubMed:15283458 ]
Ahmed D, Kumar V, Sharma M, Verma A: Target guided isolation, in-vitro antidiabetic, antioxidant activity and molecular docking studies of some flavonoids from Albizzia Lebbeck Benth. bark. BMC Complement Altern Med. 2014 May 13;14:155. doi: 10.1186/1472-6882-14-155. [PubMed:24886138 ]

Showing NP-Card for Geraldone (NP0047763)

MOL for NP0047763 (Geraldone)

3D MOL for NP0047763 (Geraldone)

3D SDF for NP0047763 (Geraldone)

3D-SDF for NP0047763 (Geraldone)

PDB for NP0047763 (Geraldone)

3D PDB for NP0047763 (Geraldone)

SMILES for NP0047763 (Geraldone)

INCHI for NP0047763 (Geraldone)

Structure for NP0047763 (Geraldone)

3D Structure for NP0047763 (Geraldone)