NP-MRD: Showing NP-Card for (6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate (NP0153717)

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Record Information

Version

2.0

Created at

2022-09-02 10:25:25 UTC

Updated at

2022-09-02 10:25:25 UTC

NP-MRD ID

NP0153717

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate

Description

(6-{2,3-Dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate belongs to the class of organic compounds known as flavonoid o-glycosides. (6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate is found in Bidens campylotheca and Bidens frondosa. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone (6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151520042D          

 36 38  0  0  0  0            999 V2000
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M  END

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M  END


  Mrv1533004151520042D          

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M  END
> <DATABASE_ID>
NP0153717

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=CC(=O)C2=CC=C(OC3OC(COC(C)=O)C(O)C(O)C3O)C(O)=C2O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O12/c1-11(25)34-10-18-21(30)22(31)23(32)24(36-18)35-17-8-5-13(19(28)20(17)29)14(26)6-3-12-4-7-16(33-2)15(27)9-12/h3-9,18,21-24,27-32H,10H2,1-2H3

> <INCHI_KEY>
UXSYWTOYZVPKHE-UHFFFAOYSA-N

> <FORMULA>
C24H26O12

> <MOLECULAR_WEIGHT>
506.46

> <EXACT_MASS>
506.142426277

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
49.930985295685396

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
1.3414500736666657

> <ALOGPS_LOGS>
-3.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.828473111398425

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.325758323414112

> <JCHEM_PKA_STRONGEST_BASIC>
-3.64910283513405

> <JCHEM_POLAR_SURFACE_AREA>
192.43999999999997

> <JCHEM_REFRACTIVITY>
122.5597

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.04e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336 -16.170   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       8.002 -16.940   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      10.669 -16.940   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669 -18.480   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003 -19.250   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.337 -18.480   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.670 -19.250   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.670 -20.790   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.004 -21.560   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      16.004 -23.100   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.338 -23.870   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      18.672 -23.100   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      20.005 -23.870   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      21.339 -23.100   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      20.005 -25.410   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      14.670 -23.870   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      14.670 -25.410   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      13.337 -23.100   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.003 -23.870   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      13.337 -21.560   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      12.003 -20.790   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      13.337 -16.940   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.670 -16.170   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.003 -16.170   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.003 -14.630   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   34                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   32                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   30                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   28                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   18   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   16   29                                                  
CONECT   29   28                                                            
CONECT   30   14   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   11   33                                                  
CONECT   33   32                                                            
CONECT   34    6   35                                                       
CONECT   35   34    3   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
(6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetic acid	Generator

Chemical Formula

C₂₄H₂₆O₁₂

Average Mass

506.4600 Da

Monoisotopic Mass

506.14243 Da

IUPAC Name

(6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate

Traditional Name

(6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=CC(=O)C2=CC=C(OC3OC(COC(C)=O)C(O)C(O)C3O)C(O)=C2O)C=C1O

InChI Identifier

InChI=1S/C24H26O12/c1-11(25)34-10-18-21(30)22(31)23(32)24(36-18)35-17-8-5-13(19(28)20(17)29)14(26)6-3-12-4-7-16(33-2)15(27)9-12/h3-9,18,21-24,27-32H,10H2,1-2H3

InChI Key

UXSYWTOYZVPKHE-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
Bidens campylotheca	LOTUS Database	35616633
Bidens frondosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid O-glycosides

Alternative Parents

Substituents

Flavonoid o-glycoside
2'-hydroxychalcone
Linear 1,3-diarylpropanoid
Cinnamylphenol
Phenolic glycoside
Hydroxycinnamic acid or derivatives
O-glycosyl compound
Glycosyl compound
Methoxyphenol
Benzoyl
Catechol
Methoxybenzene
Aryl ketone
Phenol ether
Phenoxy compound
Styrene
Anisole
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Enone
Vinylogous acid
Acryloyl-group
Alpha,beta-unsaturated ketone
Secondary alcohol
Carboxylic acid ester
Ketone
Ether
Oxacycle
Carboxylic acid derivative
Acetal
Polyol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Alcohol
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.65	ALOGPS
logP	1.34	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.33	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	122.56 m³·mol⁻¹	ChemAxon
Polarizability	49.93 Å³	ChemAxon
Number of Rings	3	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

85447318

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate (NP0153717)

MOL for NP0153717 ((6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

3D MOL for NP0153717 ((6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

3D SDF for NP0153717 ((6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

3D-SDF for NP0153717 ((6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

PDB for NP0153717 ((6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

3D PDB for NP0153717 ((6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

SMILES for NP0153717 ((6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

INCHI for NP0153717 ((6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

Structure for NP0153717 ((6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

3D Structure for NP0153717 ((6-{2,3-dihydroxy-4-[3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]phenoxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)