NP-MRD: Showing NP-Card for Apigenin 7-O-diglucuronide (NP0045259)

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Record Information

Version

1.0

Created at

2022-03-17 19:16:48 UTC

Updated at

2022-03-17 19:16:48 UTC

NP-MRD ID

NP0045259

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Apigenin 7-O-diglucuronide

Description

Apigenin 7-O-diglucuronide is found in Artemisia judaica, Plectranthus scutellarioides, Elodea canadensis, Lippia alba , Medicago sativa, Medicago truncatula, Perilla frutescens and Veronica persica.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241220502D          

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  Mrv0541 02241220502D          

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   -5.2347    1.8249    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9492    0.5874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3782    1.4123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3782    3.0624    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9492    3.8874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6637    4.2999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2348    4.2999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  2  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
  3  8  2  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  2  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
  7 11  2  0  0  0  0
  9 12  2  0  0  0  0
 18 19  1  0  0  0  0
 26 14  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 25 27  1  6  0  0  0
 24 28  1  1  0  0  0
 23 29  1  6  0  0  0
 22 30  1  1  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 38 27  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 33 38  1  0  0  0  0
 37 39  1  6  0  0  0
 36 40  1  1  0  0  0
 35 41  1  6  0  0  0
 34 42  1  1  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0045259

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](O)[C@H](O)[C@H](O[C@H]2OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)C(O)=O)O[C@@H]([C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H26O17/c28-9-3-1-8(2-4-9)13-7-12(30)15-11(29)5-10(6-14(15)41-13)40-27-23(19(34)18(33)22(43-27)25(38)39)44-26-20(35)16(31)17(32)21(42-26)24(36)37/h1-7,16-23,26-29,31-35H,(H,36,37)(H,38,39)/t16-,17-,18-,19-,20+,21-,22-,23+,26-,27+/m0/s1

> <INCHI_KEY>
SJFTVAAHLRFBST-DBFWEQBMSA-N

> <FORMULA>
C27H26O17

> <MOLECULAR_WEIGHT>
622.4851

> <EXACT_MASS>
622.116999406

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
56.14398190420773

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3S,4S,5R,6R)-6-{[(2S,3R,4S,5S,6S)-6-carboxy-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <ALOGPS_LOGP>
0.86

> <JCHEM_LOGP>
-0.6916655293333328

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.221268193618769

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.5995820675850236

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7322955043211996

> <JCHEM_POLAR_SURFACE_AREA>
279.42999999999995

> <JCHEM_REFRACTIVITY>
137.2064

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.94e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S,4S,5R,6R)-6-{[(2S,3R,4S,5S,6S)-6-carboxy-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

> <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      -1.859  -1.359   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.802   0.186   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.558  -2.174   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.212  -2.077   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.436   0.904   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -3.097   1.007   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.808  -1.462   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.615  -3.712   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.514  -1.263   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.264  -3.616   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.872   0.077   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.463   0.276   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.238   0.801   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -5.770   1.096   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.289   2.340   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.546  -0.019   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.655   3.065   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.905   0.712   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.956   2.250   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.316   2.969   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -4.437   3.406   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.437   4.946   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.770   5.716   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -7.104   4.946   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.104   3.406   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.770   2.636   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -8.438   2.636   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -8.438   5.716   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.770   7.256   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -3.103   5.716   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.103   7.256   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -1.769   4.946   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -9.771   4.946   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0     -11.105   5.716   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -12.439   4.946   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -12.439   3.406   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -11.105   2.636   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -9.771   3.406   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0     -11.105   1.096   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0     -13.773   2.636   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0     -13.773   5.716   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0     -11.105   7.256   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0     -12.439   8.026   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -9.772   8.026   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9   10                                                  
CONECT    5    2   11                                                       
CONECT    6    2   12                                                       
CONECT    7    3   11                                                       
CONECT    8    3                                                            
CONECT    9    4   12                                                       
CONECT   10    4                                                            
CONECT   11    5   13    7                                                  
CONECT   12    6   14    9                                                  
CONECT   13   11   15   16                                                  
CONECT   14   12   26                                                       
CONECT   15   13   17                                                       
CONECT   16   13   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   19                                                       
CONECT   19   17   20   18                                                  
CONECT   20   19                                                            
CONECT   21   22   26                                                       
CONECT   22   21   23   30                                                  
CONECT   23   22   24   29                                                  
CONECT   24   23   25   28                                                  
CONECT   25   24   26   27                                                  
CONECT   26   14   25   21                                                  
CONECT   27   25   38                                                       
CONECT   28   24                                                            
CONECT   29   23                                                            
CONECT   30   22   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   34   38                                                       
CONECT   34   33   35   42                                                  
CONECT   35   34   36   41                                                  
CONECT   36   35   37   40                                                  
CONECT   37   36   38   39                                                  
CONECT   38   27   37   33                                                  
CONECT   39   37                                                            
CONECT   40   36                                                            
CONECT   41   35                                                            
CONECT   42   34   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Value	Source
Apigenin-7-O-glucuronopyranosyl(1--2)-glucuronopyranoside	MeSH

Chemical Formula

C₂₇H₂₆O₁₇

Average Mass

622.4851 Da

Monoisotopic Mass

622.11700 Da

IUPAC Name

(2S,3S,4S,5R,6R)-6-{[(2S,3R,4S,5S,6S)-6-carboxy-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

Traditional Name

(2S,3S,4S,5R,6R)-6-{[(2S,3R,4S,5S,6S)-6-carboxy-4,5-dihydroxy-2-{[5-hydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}oxan-3-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H](O)[C@H](O)[C@H](O[C@H]2OC2=CC(O)=C3C(=O)C=C(OC3=C2)C2=CC=C(O)C=C2)C(O)=O)O[C@@H]([C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C27H26O17/c28-9-3-1-8(2-4-9)13-7-12(30)15-11(29)5-10(6-14(15)41-13)40-27-23(19(34)18(33)22(43-27)25(38)39)44-26-20(35)16(31)17(32)21(42-26)24(36)37/h1-7,16-23,26-29,31-35H,(H,36,37)(H,38,39)/t16-,17-,18-,19-,20+,21-,22-,23+,26-,27+/m0/s1

InChI Key

SJFTVAAHLRFBST-DBFWEQBMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia judaica	LOTUS Database	35616633
Coleus blumei	LOTUS Database	35616633
Elodea canadensis	LOTUS Database	35616633
Lippia alba	Plant	KNApSAcK
Medicago sativa	LOTUS Database	35616633
Medicago truncatula	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Verbena officinalis	FooDB	PHENOL EXPLORER
Veronica persica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glucuronides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to glucuronic acid at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glucuronides

Alternative Parents

Substituents

Flavonoid-7-o-glucuronide
Flavonoid-7-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Phenolic glycoside
1-o-glucuronide
O-glucuronide
Glucuronic acid or derivatives
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Beta-hydroxy acid
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Pyran
Dicarboxylic acid or derivatives
Oxane
Monocyclic benzene moiety
Benzenoid
Hydroxy acid
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	0.86	ALOGPS
logP	-0.69	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	2.6	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	279.43 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	137.21 m³·mol⁻¹	ChemAxon
Polarizability	56.14 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000152

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5488004

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Apigenin 7-O-diglucuronide (NP0045259)

MOL for NP0045259 (Apigenin 7-O-diglucuronide)

3D MOL for NP0045259 (Apigenin 7-O-diglucuronide)

3D SDF for NP0045259 (Apigenin 7-O-diglucuronide)

3D-SDF for NP0045259 (Apigenin 7-O-diglucuronide)

PDB for NP0045259 (Apigenin 7-O-diglucuronide)

3D PDB for NP0045259 (Apigenin 7-O-diglucuronide)

SMILES for NP0045259 (Apigenin 7-O-diglucuronide)

INCHI for NP0045259 (Apigenin 7-O-diglucuronide)

Structure for NP0045259 (Apigenin 7-O-diglucuronide)

3D Structure for NP0045259 (Apigenin 7-O-diglucuronide)