NP-MRD: Showing NP-Card for 6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate (NP0262648)

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Record Information

Version

2.0

Created at

2022-09-08 05:33:05 UTC

Updated at

2022-09-08 05:33:05 UTC

NP-MRD ID

NP0262648

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate

Description

6,7-Dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. 6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate is found in Veronica hederifolia. 6,7-Dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251508072D          

 37 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004251508072D          

 37 40  0  0  0  0            999 V2000
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 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 16 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  0  0  0  0
 21 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 13 37  1  0  0  0  0
 20 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0262648

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C(=O)OC1C(O)C(O)(CO)C2C1C=COC2OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O14/c1-33-12-6-9(2-3-11(12)26)20(31)36-18-10-4-5-34-21(14(10)23(32,8-25)19(18)30)37-22-17(29)16(28)15(27)13(7-24)35-22/h2-6,10,13-19,21-22,24-30,32H,7-8H2,1H3

> <INCHI_KEY>
OZRYKRPEVXHYIF-UHFFFAOYSA-N

> <FORMULA>
C23H30O14

> <MOLECULAR_WEIGHT>
530.479

> <EXACT_MASS>
530.163555646

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.537464736827054

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate

> <ALOGPS_LOGP>
-1.08

> <JCHEM_LOGP>
-2.5594439206666664

> <ALOGPS_LOGS>
-1.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.011796986208157

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.98780314540614

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981084760192929

> <JCHEM_POLAR_SURFACE_AREA>
225.05999999999997

> <JCHEM_REFRACTIVITY>
118.96770000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.23e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -4.297  -9.368   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.821  -7.903   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.315  -7.583   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.333  -5.798   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.698  -6.943   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.222  -8.407   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.284  -8.727   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.760 -10.192   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.887  -3.189   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.792   0.713   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.752   1.350   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.847   2.596   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.924   1.777   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.258   2.547   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.258   4.087   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.591   4.857   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.591   6.397   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.258   7.167   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       8.925   4.087   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.259   4.857   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.925   2.547   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      10.259   1.777   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.591   1.777   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   37                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   20                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   16   21   37                                                  
CONECT   21   20   22   34                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   23   33                                                  
CONECT   33   32                                                            
CONECT   34   21   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   13   20                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
6,7-Dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4ah,5H,6H,7H,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoic acid	Generator

Chemical Formula

C₂₃H₃₀O₁₄

Average Mass

530.4790 Da

Monoisotopic Mass

530.16356 Da

IUPAC Name

6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate

Traditional Name

6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1H,4aH,5H,6H,7aH-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C(=O)OC1C(O)C(O)(CO)C2C1C=COC2OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C23H30O14/c1-33-12-6-9(2-3-11(12)26)20(31)36-18-10-4-5-34-21(14(10)23(32,8-25)19(18)30)37-22-17(29)16(28)15(27)13(7-24)35-22/h2-6,10,13-19,21-22,24-30,32H,7-8H2,1H3

InChI Key

OZRYKRPEVXHYIF-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
Veronica hederifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
Coumarin
Benzopyran
Cinnamaldehyde
1-benzopyran
Phenylacetaldehyde
Anisole
Phenol ether
Styrene
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Alpha,beta-unsaturated aldehyde
Enal
Heteroaromatic compound
Lactone
Ether
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aldehyde
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	-1.1	ALOGPS
logP	-2.6	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	118.97 m³·mol⁻¹	ChemAxon
Polarizability	51.54 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

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

85293804

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate (NP0262648)

MOL for NP0262648 (6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate)

3D MOL for NP0262648 (6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate)

3D SDF for NP0262648 (6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate)

3D-SDF for NP0262648 (6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate)

PDB for NP0262648 (6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate)

3D PDB for NP0262648 (6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate)

SMILES for NP0262648 (6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate)

INCHI for NP0262648 (6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate)

Structure for NP0262648 (6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate)

3D Structure for NP0262648 (6,7-dihydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate)