NP-MRD: Showing NP-Card for 2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate (NP0213988)

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Record Information

Version

2.0

Created at

2022-09-05 13:09:10 UTC

Updated at

2022-09-05 13:09:10 UTC

NP-MRD ID

NP0213988

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate

Description

Gladiatoside C2 belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Gladiatoside C2 is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Gladiatoside C2 has been detected, but not quantified in, pulses. 2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate is found in Canavalia gladiata. This could make gladiatoside C2 a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308582D          

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M  END

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  Mrv0541 05061308582D          

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 10  8  2  0  0  0  0
 13  1  1  0  0  0  0
 14  7  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 15 10  1  0  0  0  0
 16 11  2  0  0  0  0
 16 12  1  0  0  0  0
 17  5  2  0  0  0  0
 18 11  1  0  0  0  0
 19  6  2  0  0  0  0
 19 17  1  0  0  0  0
 20 12  2  0  0  0  0
 21 18  2  0  0  0  0
 21 20  1  0  0  0  0
 22 13  1  0  0  0  0
 23 21  1  0  0  0  0
 24 22  1  0  0  0  0
 25 23  1  0  0  0  0
 26 14  1  0  0  0  0
 26 25  2  0  0  0  0
 27 24  1  0  0  0  0
 28 17  1  0  0  0  0
 29 27  1  0  0  0  0
 30 15  1  0  0  0  0
 31 18  1  0  0  0  0
 32 22  1  0  0  0  0
 33 23  2  0  0  0  0
 34 24  1  0  0  0  0
 35 25  1  0  0  0  0
 36 28  2  0  0  0  0
 37  2  1  0  0  0  0
 37 19  1  0  0  0  0
 38 13  1  0  0  0  0
 38 29  1  0  0  0  0
 39 16  1  0  0  0  0
 39 29  1  0  0  0  0
 40 20  1  0  0  0  0
 40 26  1  0  0  0  0
 41 27  1  0  0  0  0
 41 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213988

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC=C1C(=O)OC1C(O)C(O)C(C)OC1OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC=C(O)C=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H26O12/c1-13-22(32)24(34)27(41-28(36)17-5-3-4-6-19(17)37-2)29(38-13)39-16-11-18(31)21-20(12-16)40-26(25(35)23(21)33)14-7-9-15(30)10-8-14/h3-13,22,24,27,29-32,34-35H,1-2H3

> <INCHI_KEY>
LEIRBJWWXASKQN-UHFFFAOYSA-N

> <FORMULA>
C29H26O12

> <MOLECULAR_WEIGHT>
566.5095

> <EXACT_MASS>
566.142426296

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
56.572818806166424

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
3.5763352419999994

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.737797840265316

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.005593412988816

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6129303731416282

> <JCHEM_POLAR_SURFACE_AREA>
181.43999999999994

> <JCHEM_REFRACTIVITY>
141.7672

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate

> <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      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -8.002   0.000   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   37                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   17                                                       
CONECT    6    4   19                                                       
CONECT    7    9   14                                                       
CONECT    8   10   14                                                       
CONECT    9    7   15                                                       
CONECT   10    8   15                                                       
CONECT   11   16   18                                                       
CONECT   12   16   20                                                       
CONECT   13    1   22   38                                                  
CONECT   14    7    8   26                                                  
CONECT   15    9   10   30                                                  
CONECT   16   11   12   39                                                  
CONECT   17    5   19   28                                                  
CONECT   18   11   21   31                                                  
CONECT   19    6   17   37                                                  
CONECT   20   12   21   40                                                  
CONECT   21   18   20   23                                                  
CONECT   22   13   24   32                                                  
CONECT   23   21   25   33                                                  
CONECT   24   22   27   34                                                  
CONECT   25   23   26   35                                                  
CONECT   26   14   25   40                                                  
CONECT   27   24   29   41                                                  
CONECT   28   17   36   41                                                  
CONECT   29   27   38   39                                                  
CONECT   30   15                                                            
CONECT   31   18                                                            
CONECT   32   22                                                            
CONECT   33   23                                                            
CONECT   34   24                                                            
CONECT   35   25                                                            
CONECT   36   28                                                            
CONECT   37    2   19                                                       
CONECT   38   13   29                                                       
CONECT   39   16   29                                                       
CONECT   40   20   26                                                       
CONECT   41   27   28                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoic acid	Generator

Chemical Formula

C₂₉H₂₆O₁₂

Average Mass

566.5095 Da

Monoisotopic Mass

566.14243 Da

IUPAC Name

2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate

Traditional Name

2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC=CC=C1C(=O)OC1C(O)C(O)C(C)OC1OC1=CC(O)=C2C(OC(=C(O)C2=O)C2=CC=C(O)C=C2)=C1

InChI Identifier

InChI=1S/C29H26O12/c1-13-22(32)24(34)27(41-28(36)17-5-3-4-6-19(17)37-2)29(38-13)39-16-11-18(31)21-20(12-16)40-26(25(35)23(21)33)14-7-9-15(30)10-8-14/h3-13,22,24,27,29-32,34-35H,1-2H3

InChI Key

LEIRBJWWXASKQN-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Canavalia gladiata	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
3-hydroxyflavone
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Phenolic glycoside
Hexose monosaccharide
O-methoxybenzoic acid or derivatives
O-glycosyl compound
Glycosyl compound
Chromone
Benzoate ester
Benzopyran
1-benzopyran
Benzoic acid or derivatives
Phenol ether
Phenoxy compound
Methoxybenzene
Benzoyl
Anisole
Alkyl aryl ether
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Monosaccharide
Vinylogous acid
Heteroaromatic compound
Carboxylic acid ester
Secondary alcohol
1,2-diol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Ether
Oxacycle
Organic oxide
Alcohol
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
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	3.01	ALOGPS
logP	3.58	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.01	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	181.44 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	141.77 m³·mol⁻¹	ChemAxon
Polarizability	56.57 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

HMDB0036254

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015118

KNApSAcK ID

C00032999

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

85261790

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate (NP0213988)

MOL for NP0213988 (2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate)

3D MOL for NP0213988 (2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate)

3D SDF for NP0213988 (2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate)

3D-SDF for NP0213988 (2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate)

PDB for NP0213988 (2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate)

3D PDB for NP0213988 (2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate)

SMILES for NP0213988 (2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate)

INCHI for NP0213988 (2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate)

Structure for NP0213988 (2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate)

3D Structure for NP0213988 (2-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy}-4,5-dihydroxy-6-methyloxan-3-yl 2-methoxybenzoate)