NP-MRD: Showing NP-Card for 5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid (NP0159340)

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Record Information

Version

2.0

Created at

2022-09-02 17:04:42 UTC

Updated at

2022-09-02 17:04:42 UTC

NP-MRD ID

NP0159340

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

Description

5-(Acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid 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. 5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid is found in Meehania fargesii. 5-(Acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241518122D          

 37 40  0  0  0  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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
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  1  2  1  0  0  0  0
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 10 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004241518122D          

 37 40  0  0  0  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0159340

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1O)C1=CC(=O)C2=C(O)C=C(OC3OC(C(O)C(O)C3OC(C)=O)C(O)=O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C24H22O13/c1-9(25)34-22-20(30)19(29)21(23(31)32)37-24(22)35-11-6-13(27)18-14(28)8-16(36-17(18)7-11)10-3-4-15(33-2)12(26)5-10/h3-8,19-22,24,26-27,29-30H,1-2H3,(H,31,32)

> <INCHI_KEY>
BKUMLOAEBSPBOC-UHFFFAOYSA-N

> <FORMULA>
C24H22O13

> <MOLECULAR_WEIGHT>
518.427

> <EXACT_MASS>
518.106040768

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
49.7767482712994

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
1.0423497229999996

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.311655887183617

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.801940903712892

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7016636599146375

> <JCHEM_POLAR_SURFACE_AREA>
198.51

> <JCHEM_REFRACTIVITY>
120.54040000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.19e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -0.770   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  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    6   11   37                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   36                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   35                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   27                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   32                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   20   28                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   22   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   18   36                                                       
CONECT   36   35   14   37                                                  
CONECT   37   36   10                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
5-(Acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylate	Generator

Chemical Formula

C₂₄H₂₂O₁₃

Average Mass

518.4270 Da

Monoisotopic Mass

518.10604 Da

IUPAC Name

5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid

Traditional Name

5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1O)C1=CC(=O)C2=C(O)C=C(OC3OC(C(O)C(O)C3OC(C)=O)C(O)=O)C=C2O1

InChI Identifier

InChI=1S/C24H22O13/c1-9(25)34-22-20(30)19(29)21(23(31)32)37-24(22)35-11-6-13(27)18-14(28)8-16(36-17(18)7-11)10-3-4-15(33-2)12(26)5-10/h3-8,19-22,24,26-27,29-30H,1-2H3,(H,31,32)

InChI Key

BKUMLOAEBSPBOC-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
Meehania fargesii	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
4p-methoxyflavonoid-skeleton
Flavone
Hydroxyflavonoid
5-hydroxyflavonoid
3'-hydroxyflavonoid
Phenolic glycoside
O-glucuronide
1-o-glucuronide
Glucuronic acid or derivatives
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Pyranone
Beta-hydroxy acid
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Pyran
Oxane
Hydroxy acid
Monosaccharide
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
1,2-diol
Carboxylic acid ester
Acetal
Ether
Oxacycle
Carboxylic acid
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
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	1.94	ALOGPS
logP	1.04	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	2.8	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	198.51 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	120.54 m³·mol⁻¹	ChemAxon
Polarizability	49.78 Å³	ChemAxon
Number of Rings	4	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

Not Available

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

75150022

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid (NP0159340)

MOL for NP0159340 (5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D MOL for NP0159340 (5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D SDF for NP0159340 (5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D-SDF for NP0159340 (5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

PDB for NP0159340 (5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D PDB for NP0159340 (5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

SMILES for NP0159340 (5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

INCHI for NP0159340 (5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

Structure for NP0159340 (5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)

3D Structure for NP0159340 (5-(acetyloxy)-3,4-dihydroxy-6-{[5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-4-oxochromen-7-yl]oxy}oxane-2-carboxylic acid)