NP-MRD: Showing NP-Card for {6-[2-(2h-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0309007)

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Record Information

Version

1.0

Created at

2022-09-11 03:14:41 UTC

Updated at

2022-09-11 03:14:41 UTC

NP-MRD ID

NP0309007

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{6-[2-(2h-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

Description

{6-[2-(2H-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. {6-[2-(2h-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate is found in Prunus ssiori. {6-[2-(2H-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004201504092D          

 35 38  0  0  0  0            999 V2000
    4.7812    6.8854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    6.8854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    7.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391    6.8854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    8.1229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    8.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    9.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    9.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   10.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   11.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   11.8354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246   10.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6391   11.0104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9246    9.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    4.4104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    5.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    6.0604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 34 35  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004201504092D          

 35 38  0  0  0  0            999 V2000
    4.7812    6.8854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    6.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0309007

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1C(COC(=O)C=CC2=CC=C(O)C(O)=C2)OC(OCCC2=CC=C3OCOC3=C2)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O11/c25-15-4-1-13(9-16(15)26)3-6-20(27)32-11-19-21(28)22(29)23(30)24(35-19)31-8-7-14-2-5-17-18(10-14)34-12-33-17/h1-6,9-10,19,21-26,28-30H,7-8,11-12H2

> <INCHI_KEY>
YPRSXUHIUFIKFR-UHFFFAOYSA-N

> <FORMULA>
C24H26O11

> <MOLECULAR_WEIGHT>
490.461

> <EXACT_MASS>
490.147511657

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
49.13517519952998

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{6-[2-(2H-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
1.7737151503333337

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.067408983516485

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.20820528646917

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490922422252474

> <JCHEM_POLAR_SURFACE_AREA>
164.37

> <JCHEM_REFRACTIVITY>
119.33860000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{6-[2-(2H-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  O   UNK     0       8.925  12.853   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.925  11.313   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.259  10.543   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.592  11.313   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.592  12.853   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      12.926  13.623   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      14.260  12.853   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      12.926  15.163   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.592  15.933   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.592  17.473   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.259  18.243   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.259  19.783   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.592  20.553   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.592  22.093   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      12.926  19.783   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.260  20.553   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.926  18.243   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.259   9.003   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.925   8.233   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.925   6.693   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.591   9.003   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.258   8.233   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.591  10.543   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.258  11.313   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   10                                                       
CONECT   18    3   19                                                       
CONECT   19   18   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   31                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   26   31                                                  
CONECT   31   30   23                                                       
CONECT   32   19   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32    2   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
{6-[2-(2H-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₄H₂₆O₁₁

Average Mass

490.4610 Da

Monoisotopic Mass

490.14751 Da

IUPAC Name

{6-[2-(2H-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

{6-[2-(2H-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

OC1C(COC(=O)C=CC2=CC=C(O)C(O)=C2)OC(OCCC2=CC=C3OCOC3=C2)C(O)C1O

InChI Identifier

InChI=1S/C24H26O11/c25-15-4-1-13(9-16(15)26)3-6-20(27)32-11-19-21(28)22(29)23(30)24(35-19)31-8-7-14-2-5-17-18(10-14)34-12-33-17/h1-6,9-10,19,21-26,28-30H,7-8,11-12H2

InChI Key

YPRSXUHIUFIKFR-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
Prunus ssiori	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Glycosyl compound
O-glycosyl compound
Benzodioxole
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Monosaccharide
Oxane
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Acetal
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Polyol
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
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	1.12	ALOGPS
logP	1.77	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164.37 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	119.34 m³·mol⁻¹	ChemAxon
Polarizability	49.14 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

Not Available

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-(2h-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate (NP0309007)

MOL for NP0309007 ({6-[2-(2h-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D MOL for NP0309007 ({6-[2-(2h-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D SDF for NP0309007 ({6-[2-(2h-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D-SDF for NP0309007 ({6-[2-(2h-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

PDB for NP0309007 ({6-[2-(2h-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D PDB for NP0309007 ({6-[2-(2h-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

SMILES for NP0309007 ({6-[2-(2h-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

INCHI for NP0309007 ({6-[2-(2h-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

Structure for NP0309007 ({6-[2-(2h-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate)

3D Structure for NP0309007 ({6-[2-(2h-1,3-benzodioxol-5-yl)ethoxy]-3,4,5-trihydroxyoxan-2-yl}methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate)