NP-MRD: Showing NP-Card for Demethylnobiletin (NP0048837)

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Record Information

Version

2.0

Created at

2022-03-17 21:02:57 UTC

Updated at

2022-03-17 21:02:57 UTC

NP-MRD ID

NP0048837

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Demethylnobiletin

Description

Demethylnobiletin belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, demethylnobiletin is considered to be a flavonoid lipid molecule. Demethylnobiletin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Demethylnobiletin has been detected, but not quantified in, several different foods, such as citrus, spearmints, peppermints, mandarin orange (clementine, tangerine), and herbs and spices. Demethylnobiletin is found in Antirrhinum graniticum, Baccharis thymifolia, Citrus aurantium , Citrus depressa, Citrus japonica, Citrus kinokuni, Citrus sinensis, Citrus spp., Citrus tangerina , Citrus unshiu, Cunila incana, Mentha piperita, Mentha pulegium, Micromeria albanica, Murraya paniculata , Ocimum americanum, Ocimum americanum var. americanum , Oxalis pes-caprae, Relhania corymbosa, Sideritis jahandiezii, Sideritis mugronensis, Sideritis tragoriganum, Stachys aegyptiaca, Thymus sp. and Xinhui citrus. This could make demethylnobiletin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 02241220192D          

 28 30  0  0  0  0            999 V2000
   -2.2982   -0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0127   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0127   -1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2982   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837   -1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693   -0.7366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1548   -1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1548   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5597   -0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2741    0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5597    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2741   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9886   -0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9886    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2982    0.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7272   -0.7366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7272   -2.3866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2982   -3.2116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693   -3.2116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7031    0.5009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7031    1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7031   -1.1491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175   -0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4416   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837    0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7272   -3.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  7  6  1  0  0  0  0
  5  6  1  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  1  0  0  0  0
 11 14  2  0  0  0  0
 12 13  2  0  0  0  0
 12 16  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  1 17  1  0  0  0  0
  2 18  1  0  0  0  0
  3 19  1  0  0  0  0
  4 20  1  0  0  0  0
  8 21  2  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 26  1  0  0  0  0
 17 27  1  0  0  0  0
 19 28  1  0  0  0  0
M  END

  Mrv0541 02241220192D          

 28 30  0  0  0  0            999 V2000
   -2.2982   -0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0127   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0127   -1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2982   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837   -1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693   -0.7366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1548   -1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1548   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5597   -0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2741    0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5597    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2741   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9886   -0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9886    0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2982    0.0884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7272   -0.7366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7272   -2.3866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2982   -3.2116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8693   -3.2116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7031    0.5009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7031    1.3259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7031   -1.1491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4175   -0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4416   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5837    0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7272   -3.2116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  7  6  1  0  0  0  0
  5  6  1  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  1  0  0  0  0
 11 14  2  0  0  0  0
 12 13  2  0  0  0  0
 12 16  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
  1 17  1  0  0  0  0
  2 18  1  0  0  0  0
  3 19  1  0  0  0  0
  4 20  1  0  0  0  0
  8 21  2  0  0  0  0
 16 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 24  1  0  0  0  0
 24 25  1  0  0  0  0
 18 26  1  0  0  0  0
 17 27  1  0  0  0  0
 19 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048837

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C(C=C1)C1=CC(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O8/c1-23-12-7-6-10(8-14(12)24-2)13-9-11(21)15-16(22)18(25-3)20(27-5)19(26-4)17(15)28-13/h6-9,22H,1-5H3

> <INCHI_KEY>
DOFJNFPSMUCECH-UHFFFAOYSA-N

> <FORMULA>
C20H20O8

> <MOLECULAR_WEIGHT>
388.368

> <EXACT_MASS>
388.115817616

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
39.76483168871021

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,4-dimethoxyphenyl)-5-hydroxy-6,7,8-trimethoxy-4H-chromen-4-one

> <ALOGPS_LOGP>
2.89

> <JCHEM_LOGP>
2.525463448666666

> <ALOGPS_LOGS>
-4.10

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.911619664383473

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.664364385317024

> <JCHEM_PKA_STRONGEST_BASIC>
-4.218012913231579

> <JCHEM_POLAR_SURFACE_AREA>
92.68

> <JCHEM_REFRACTIVITY>
101.26809999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
demethylnobiletin

> <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      -4.290  -1.375   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.624  -2.145   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.624  -3.685   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.290  -4.455   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.956  -3.685   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.956  -2.145   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.623  -1.375   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.623  -4.455   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.289  -3.685   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.289  -2.145   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.045  -1.375   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.378   0.935   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.045   0.165   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.378  -2.145   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.712  -1.375   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.712   0.165   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -4.290   0.165   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -6.957  -1.375   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -6.957  -4.455   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.290  -5.995   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.623  -5.995   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.046   0.935   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.046   2.475   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       5.046  -2.145   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.379  -1.375   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -8.291  -2.145   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.956   0.935   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.957  -5.995   0.000  0.00  0.00           C+0
CONECT    1    2    6   17                                                  
CONECT    2    1    3   18                                                  
CONECT    3    2    4   19                                                  
CONECT    4    3    5   20                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16                                                       
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   12   15   22                                                  
CONECT   17    1   27                                                       
CONECT   18    2   26                                                       
CONECT   19    3   28                                                       
CONECT   20    4                                                            
CONECT   21    8                                                            
CONECT   22   16   23                                                       
CONECT   23   22                                                            
CONECT   24   15   25                                                       
CONECT   25   24                                                            
CONECT   26   18                                                            
CONECT   27   17                                                            
CONECT   28   19                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
5-Demethyl nobiletin	HMDB
2-(3,4-Dimethoxyphenyl)-5-hydroxy-6,7,8-trimethoxy-4H-1-benzopyran-4-one	HMDB
5-Demethylnobiletin	HMDB
5-Desmethoxynobiletin (incorr.)	HMDB
5-Hydroxy-3',4',6,7,8-pentamethoxyflavone	HMDB
5-Hydroxy-6,7,8,3',4'-pentamethoxyflavone	HMDB
5-O-Demethylnobiletin	HMDB

Chemical Formula

C₂₀H₂₀O₈

Average Mass

388.3680 Da

Monoisotopic Mass

388.11582 Da

IUPAC Name

2-(3,4-dimethoxyphenyl)-5-hydroxy-6,7,8-trimethoxy-4H-chromen-4-one

Traditional Name

demethylnobiletin

CAS Registry Number

2174-59-6

SMILES

COC1=C(OC)C=C(C=C1)C1=CC(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O1

InChI Identifier

InChI=1S/C20H20O8/c1-23-12-7-6-10(8-14(12)24-2)13-9-11(21)15-16(22)18(25-3)20(27-5)19(26-4)17(15)28-13/h6-9,22H,1-5H3

InChI Key

DOFJNFPSMUCECH-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Antirrhinum graniticum	Plant	KNApSAcK
Baccharis thymifolia	LOTUS Database	35616633
Citrus aurantium	Plant	KNApSAcK
Citrus depressa	LOTUS Database	35616633
Citrus japonica	LOTUS Database	35616633
Citrus kinokuni	LOTUS Database	35616633
Citrus reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus sinensis	LOTUS Database	35616633
Citrus spp.	Plant	KNApSAcK
Citrus tangerina	Plant	KNApSAcK
Citrus unshiu	LOTUS Database	35616633
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	KNAPSACK
Cunila incana	Plant	KNApSAcK
Mentha piperita	LOTUS Database	35616633
Mentha pulegium	LOTUS Database	35616633
Mentha spicata	FooDB	KNAPSACK
Mentha x piperita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Micromeria albanica	Plant	KNApSAcK
Murraya paniculata	Plant	KNApSAcK
Ocimum americanum	LOTUS Database	35616633
Ocimum americanum var. americanum	Plant	KNApSAcK
Oxalis pes-caprae	LOTUS Database	35616633
Relhania corymbosa	LOTUS Database	35616633
Satureja montana	FooDB	KNAPSACK
Sideritis jahandiezii	Plant	KNApSAcK
Sideritis mugronensis	Plant	KNApSAcK
Sideritis tragoriganum	LOTUS Database	35616633
Stachys aegyptiaca	LOTUS Database	35616633
Thymus sp.	Plant	KNApSAcK
Xinhui citrus	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

8-O-methylated flavonoids

Alternative Parents

Substituents

3p-methoxyflavonoid-skeleton
4p-methoxyflavonoid-skeleton
6-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
8-methoxyflavonoid-skeleton
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
O-dimethoxybenzene
Dimethoxybenzene
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Pyranone
Benzenoid
Monocyclic benzene moiety
Pyran
Vinylogous acid
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavones and Flavonols (LMPK12111479 )

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	2.89	ALOGPS
logP	2.53	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.66	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	92.68 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	101.27 m³·mol⁻¹	ChemAxon
Polarizability	39.76 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	Yes	ChemAxon

External Links

HMDB ID

HMDB0037571

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016659

KNApSAcK ID

C00003936

Chemspider ID

318578

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

358832

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Demethylnobiletin (NP0048837)

MOL for NP0048837 (Demethylnobiletin)

3D MOL for NP0048837 (Demethylnobiletin)

3D SDF for NP0048837 (Demethylnobiletin)

3D-SDF for NP0048837 (Demethylnobiletin)

PDB for NP0048837 (Demethylnobiletin)

3D PDB for NP0048837 (Demethylnobiletin)

SMILES for NP0048837 (Demethylnobiletin)

INCHI for NP0048837 (Demethylnobiletin)

Structure for NP0048837 (Demethylnobiletin)

3D Structure for NP0048837 (Demethylnobiletin)