NP-MRD: Showing NP-Card for 4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate (NP0291024)

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Record Information

Version

2.0

Created at

2022-09-09 21:57:35 UTC

Updated at

2022-09-09 21:57:35 UTC

NP-MRD ID

NP0291024

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate

Description

4-{[3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes: Hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol). 4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate is found in Balanophora japonica. 4-{[3-(3,4-Dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171509382D          

 35 37  0  0  0  0            999 V2000
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004171509382D          

 35 37  0  0  0  0            999 V2000
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    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0291024

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1OC(O)C(O)C(OC(=O)C=CC2=CC=C(O)C(O)=C2)C1OC(=O)C1=CC(O)=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O13/c23-8-15-19(35-21(31)10-6-13(26)17(29)14(27)7-10)20(18(30)22(32)33-15)34-16(28)4-2-9-1-3-11(24)12(25)5-9/h1-7,15,18-20,22-27,29-30,32H,8H2

> <INCHI_KEY>
IBBFQDJMEDTWOD-UHFFFAOYSA-N

> <FORMULA>
C22H22O13

> <MOLECULAR_WEIGHT>
494.405

> <EXACT_MASS>
494.106040768

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
45.50157402170098

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
1.01

> <JCHEM_LOGP>
1.0788247403333324

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.234363803889423

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.070119049055608

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981823116519749

> <JCHEM_POLAR_SURFACE_AREA>
223.66999999999996

> <JCHEM_REFRACTIVITY>
115.21759999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.03e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000  -7.700   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15                                                       
CONECT   23    9    3   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   35                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   27                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoic acid	Generator

Chemical Formula

C₂₂H₂₂O₁₃

Average Mass

494.4050 Da

Monoisotopic Mass

494.10604 Da

IUPAC Name

4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate

Traditional Name

4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OCC1OC(O)C(O)C(OC(=O)C=CC2=CC=C(O)C(O)=C2)C1OC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C22H22O13/c23-8-15-19(35-21(31)10-6-13(26)17(29)14(27)7-10)20(18(30)22(32)33-15)34-16(28)4-2-9-1-3-11(24)12(25)5-9/h1-7,15,18-20,22-27,29-30,32H,8H2

InChI Key

IBBFQDJMEDTWOD-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
Balanophora japonica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tannins. These are naturally occurring polyphenols which be categorized into four main classes: Hydrolyzable tannin (based on ellagic acid or gallic acid), condensed tannins (made of oligomeric or polymeric proanthocyanidins), complex tannins (made of a catechin bound to a gallotannin or elagitannin), and phlorotannins (oligomers of phloroglucinol).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Not Available

Direct Parent

Tannins

Alternative Parents

Substituents

Tannin
Galloyl ester
Cinnamic acid ester
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
Coumaric acid or derivatives
Gallic acid or derivatives
Hexose monosaccharide
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Benzoyl
Styrene
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Oxane
Monosaccharide
Benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Hemiacetal
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Alcohol
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	1.01	ALOGPS
logP	1.08	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.07	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	223.67 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	115.22 m³·mol⁻¹	ChemAxon
Polarizability	45.5 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

85302284

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate (NP0291024)

MOL for NP0291024 (4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D MOL for NP0291024 (4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D SDF for NP0291024 (4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0291024 (4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

PDB for NP0291024 (4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D PDB for NP0291024 (4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

SMILES for NP0291024 (4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

INCHI for NP0291024 (4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

Structure for NP0291024 (4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)

3D Structure for NP0291024 (4-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5,6-dihydroxy-2-(hydroxymethyl)oxan-3-yl 3,4,5-trihydroxybenzoate)