NP-MRD: Showing NP-Card for 2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2h-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate (NP0143706)

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Record Information

Version

2.0

Created at

2022-09-01 22:32:07 UTC

Updated at

2022-09-01 22:32:07 UTC

NP-MRD ID

NP0143706

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2h-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate

Description

CHEMBL452635 belongs to the class of organic compounds known as 5-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-5 position of the flavonoid skeleton. 2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2h-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate is found in Pithecellobium clypearia. Based on a literature review very few articles have been published on CHEMBL452635.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022200322D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309022200322D          

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 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 27 35  1  0  0  0  0
 23 36  1  0  0  0  0
 36 37  2  0  0  0  0
 19 37  1  0  0  0  0
 37 38  1  0  0  0  0
 16 38  1  0  0  0  0
 15 39  1  0  0  0  0
 39 40  2  0  0  0  0
 11 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0143706

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(=CC(O)=C1O)C(=O)OC1=CC(O)=C2CCC(OC2=C1)C1=CC(O)=C(OC(=O)OC2=CC=CC=C2)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H22O12/c30-19-12-17(38-28(36)15-10-20(31)26(35)21(32)11-15)13-25-18(19)6-7-24(40-25)14-8-22(33)27(23(34)9-14)41-29(37)39-16-4-2-1-3-5-16/h1-5,8-13,24,30-35H,6-7H2

> <INCHI_KEY>
VLAANOKIZGGKIT-UHFFFAOYSA-N

> <FORMULA>
C29H22O12

> <MOLECULAR_WEIGHT>
562.483

> <EXACT_MASS>
562.111126148

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
56.16013502898273

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2H-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
4.39

> <JCHEM_LOGP>
7.108825950666665

> <ALOGPS_LOGS>
-4.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.15318436699399

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.029082374407274

> <JCHEM_PKA_STRONGEST_BASIC>
-4.08221381929834

> <JCHEM_POLAR_SURFACE_AREA>
192.44

> <JCHEM_REFRACTIVITY>
140.9365

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2H-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.670  -2.310   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      14.670  -5.390   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      12.003  -6.930   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4                                                       
CONECT   10    2   11                                                       
CONECT   11   10   12   40                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   39                                                  
CONECT   16   15   17   38                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   37                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   36                                                  
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                                                       
CONECT   36   23   37                                                       
CONECT   37   36   19   38                                                  
CONECT   38   37   16                                                       
CONECT   39   15   40                                                       
CONECT   40   39   11   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₂₂O₁₂

Average Mass

562.4830 Da

Monoisotopic Mass

562.11113 Da

IUPAC Name

2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2H-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate

Traditional Name

2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2H-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OC1=CC(=CC(O)=C1O)C(=O)OC1=CC(O)=C2CCC(OC2=C1)C1=CC(O)=C(OC(=O)OC2=CC=CC=C2)C(O)=C1

InChI Identifier

InChI=1S/C29H22O12/c30-19-12-17(38-28(36)15-10-20(31)26(35)21(32)11-15)13-25-18(19)6-7-24(40-25)14-8-22(33)27(23(34)9-14)41-29(37)39-16-4-2-1-3-5-16/h1-5,8-13,24,30-35H,6-7H2

InChI Key

VLAANOKIZGGKIT-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
Archidendron clypearia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-5 position of the flavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Hydroxyflavonoids

Direct Parent

5-hydroxyflavonoids

Alternative Parents

Substituents

5-hydroxyflavonoid
3'-hydroxyflavonoid
Flavan
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid ester
M-hydroxybenzoic acid ester
Benzopyran
Chromane
Benzoate ester
1-benzopyran
Benzenetriol
Benzoic acid or derivatives
Pyrogallol derivative
Benzoyl
Phenoxy compound
Resorcinol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Carbonic acid diester
Carbonic acid derivative
Carboxylic acid ester
Ether
Monocarboxylic acid or derivatives
Polyol
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	4.39	ALOGPS
logP	7.11	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	8.03	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	192.44 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	140.94 m³·mol⁻¹	ChemAxon
Polarizability	56.16 Å³	ChemAxon
Number of Rings	5	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

9881474

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11706751

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2h-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate (NP0143706)

MOL for NP0143706 (2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2h-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate)

3D MOL for NP0143706 (2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2h-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate)

3D SDF for NP0143706 (2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2h-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate)

3D-SDF for NP0143706 (2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2h-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate)

PDB for NP0143706 (2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2h-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate)

3D PDB for NP0143706 (2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2h-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate)

SMILES for NP0143706 (2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2h-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate)

INCHI for NP0143706 (2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2h-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate)

Structure for NP0143706 (2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2h-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate)

3D Structure for NP0143706 (2-{3,5-dihydroxy-4-[(phenoxycarbonyl)oxy]phenyl}-5-hydroxy-3,4-dihydro-2h-1-benzopyran-7-yl 3,4,5-trihydroxybenzoate)