NP-MRD: Showing NP-Card for Kaempferol 3-O-(6"-malonyl-glucoside) (NP0045263)

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Record Information

Version

2.0

Created at

2022-03-17 19:16:52 UTC

Updated at

2022-03-17 19:16:52 UTC

NP-MRD ID

NP0045263

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Kaempferol 3-O-(6"-malonyl-glucoside)

Description

Kaempferol 3-O-(6"-malonyl-glucoside) is found in Ceterach officinarum , Cicer sp., Equisetum spp. and Pyrus communis .

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241223302D          

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M  END

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M  END
> <DATABASE_ID>
NP0045263

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@H](O)[C@@H](COC(=O)CC(O)=O)O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H22O14/c25-10-3-1-9(2-4-10)22-23(19(32)17-12(27)5-11(26)6-13(17)36-22)38-24-21(34)20(33)18(31)14(37-24)8-35-16(30)7-15(28)29/h1-6,14,18,20-21,24-27,31,33-34H,7-8H2,(H,28,29)/t14-,18-,20+,21-,24+/m1/s1

> <INCHI_KEY>
XEXCLTHHXIWUHO-UJKBSQBPSA-N

> <FORMULA>
C24H22O14

> <MOLECULAR_WEIGHT>
534.4231

> <EXACT_MASS>
534.100955412

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
49.689672893778926

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2R,3S,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-3-oxopropanoic acid

> <ALOGPS_LOGP>
1.21

> <JCHEM_LOGP>
0.49208388199999986

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.434374749024219

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4855408992338304

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491030749341817

> <JCHEM_POLAR_SURFACE_AREA>
229.73999999999998

> <JCHEM_REFRACTIVITY>
122.79019999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(2R,3S,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-3-oxopropanoic 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      -5.511   5.940   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.845   5.170   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.845   3.630   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.511   2.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.178   3.630   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.178   5.170   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.844   5.940   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.844   2.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.510   3.630   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.510   5.170   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.177   5.940   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.157   8.250   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.177   7.480   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.157   5.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.491   5.940   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.491   7.480   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.844   1.320   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.177   2.860   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -8.179   5.940   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -5.511   1.320   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.824   8.250   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.510   0.550   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.510  -0.990   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.176  -1.760   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.157  -0.990   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.157   0.550   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.177   1.320   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.491   1.320   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.491  -1.760   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.176  -3.300   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.844  -1.760   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.844  -3.300   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -8.179  -3.300   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -6.845  -4.070   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.511  -3.300   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.178  -4.070   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.845  -5.610   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -4.178  -5.610   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   20                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   17                                                  
CONECT    9    8   10   18                                                  
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                                                       
CONECT   16   12   15   21                                                  
CONECT   17    8                                                            
CONECT   18    9   27                                                       
CONECT   19    2                                                            
CONECT   20    4                                                            
CONECT   21   16                                                            
CONECT   22   23   27                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25   30                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   18   22   26                                                  
CONECT   28   26                                                            
CONECT   29   25                                                            
CONECT   30   24                                                            
CONECT   31   23   32                                                       
CONECT   32   31   36                                                       
CONECT   33   34                                                            
CONECT   34   33   35   37                                                  
CONECT   35   34   36                                                       
CONECT   36   32   35   38                                                  
CONECT   37   34                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₂O₁₄

Average Mass

534.4231 Da

Monoisotopic Mass

534.10096 Da

IUPAC Name

3-{[(2R,3S,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-3-oxopropanoic acid

Traditional Name

3-{[(2R,3S,4S,5R,6S)-6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-3-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H](O)[C@@H](COC(=O)CC(O)=O)O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@@H]1O

InChI Identifier

InChI=1S/C24H22O14/c25-10-3-1-9(2-4-10)22-23(19(32)17-12(27)5-11(26)6-13(17)36-22)38-24-21(34)20(33)18(31)14(37-24)8-35-16(30)7-15(28)29/h1-6,14,18,20-21,24-27,31,33-34H,7-8H2,(H,28,29)/t14-,18-,20+,21-,24+/m1/s1

InChI Key

XEXCLTHHXIWUHO-UJKBSQBPSA-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
Ceterach officinarum	Plant	KNApSAcK
Cicer sp.	Plant	KNApSAcK
Cichorium endivia	FooDB	PHENOL EXPLORER
Equisetum spp.	Plant	KNApSAcK
Lactuca sativa	FooDB	PHENOL EXPLORER
Pyrus communis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Glycosyl compound
O-glycosyl compound
Chromone
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Pyran
Oxane
1,3-dicarbonyl compound
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Carboxylic acid ester
Acetal
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Carboxylic acid
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen 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	1.21	ALOGPS
logP	0.49	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.49	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	229.74 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	122.79 m³·mol⁻¹	ChemAxon
Polarizability	49.69 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

FDB000188

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

14162699

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Kaempferol 3-O-(6"-malonyl-glucoside) (NP0045263)

MOL for NP0045263 (Kaempferol 3-O-(6"-malonyl-glucoside))

3D MOL for NP0045263 (Kaempferol 3-O-(6"-malonyl-glucoside))

3D SDF for NP0045263 (Kaempferol 3-O-(6"-malonyl-glucoside))

3D-SDF for NP0045263 (Kaempferol 3-O-(6"-malonyl-glucoside))

PDB for NP0045263 (Kaempferol 3-O-(6"-malonyl-glucoside))

3D PDB for NP0045263 (Kaempferol 3-O-(6"-malonyl-glucoside))

SMILES for NP0045263 (Kaempferol 3-O-(6"-malonyl-glucoside))

INCHI for NP0045263 (Kaempferol 3-O-(6"-malonyl-glucoside))

Structure for NP0045263 (Kaempferol 3-O-(6"-malonyl-glucoside))

3D Structure for NP0045263 (Kaempferol 3-O-(6"-malonyl-glucoside))