NP-MRD: Showing NP-Card for (6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate (NP0211462)

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Record Information

Version

2.0

Created at

2022-09-05 09:45:00 UTC

Updated at

2022-09-05 09:45:00 UTC

NP-MRD ID

NP0211462

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate

Description

(6-{[3-(Hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose (6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-8-yl]oxy}-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


  Mrv1533004241503132D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004241503132D          

 36 38  0  0  0  0            999 V2000
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 30 25  1  4  0  0  0
 30 31  2  0  0  0  0
 32 31  1  4  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  4  0  0  0
M  END
> <DATABASE_ID>
NP0211462

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC2OC(COC(C)=O)C(O)C(O)C2O)=C2C(=O)OC(CC2=C1C)C=CC=CC=CC

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O10/c1-5-6-7-8-9-10-16-11-17-14(2)18(32-4)12-19(21(17)25(31)34-16)35-26-24(30)23(29)22(28)20(36-26)13-33-15(3)27/h5-10,12,16,20,22-24,26,28-30H,11,13H2,1-4H3

> <INCHI_KEY>
HFNVEOAKDZDOHA-UHFFFAOYSA-N

> <FORMULA>
C26H32O10

> <MOLECULAR_WEIGHT>
504.532

> <EXACT_MASS>
504.19954723

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.49241505566795

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.27393664

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.21068649356166

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.201674445839975

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649102819550402

> <JCHEM_POLAR_SURFACE_AREA>
140.98

> <JCHEM_REFRACTIVITY>
131.31769999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   19                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    9   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    7   20                                                  
CONECT   20   19                                                            
CONECT   21    5   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   21   28                                                  
CONECT   28   27    3   29                                                  
CONECT   29   28                                                            
CONECT   30   25   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   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-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetic acid	Generator

Chemical Formula

C₂₆H₃₂O₁₀

Average Mass

504.5320 Da

Monoisotopic Mass

504.19955 Da

IUPAC Name

(6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-1H-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate

Traditional Name

(6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate

CAS Registry Number

Not Available

SMILES

COC1=CC(OC2OC(COC(C)=O)C(O)C(O)C2O)=C2C(=O)OC(CC2=C1C)C=CC=CC=CC

InChI Identifier

InChI=1S/C26H32O10/c1-5-6-7-8-9-10-16-11-17-14(2)18(32-4)12-19(21(17)25(31)34-16)35-26-24(30)23(29)22(28)20(36-26)13-33-15(3)27/h5-10,12,16,20,22-24,26,28-30H,11,13H2,1-4H3

InChI Key

HFNVEOAKDZDOHA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
O-glycosyl compound
Benzopyran
Isochromane
2-benzopyran
Anisole
Alkyl aryl ether
Benzenoid
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Lactone
Carboxylic acid ester
Secondary alcohol
Organoheterocyclic compound
Ether
Oxacycle
Carboxylic acid derivative
Acetal
Polyol
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
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	2.48	ALOGPS
logP	2.27	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	140.98 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	131.32 m³·mol⁻¹	ChemAxon
Polarizability	53.49 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	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

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-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate (NP0211462)

MOL for NP0211462 ((6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

3D MOL for NP0211462 ((6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

3D SDF for NP0211462 ((6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

3D-SDF for NP0211462 ((6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

PDB for NP0211462 ((6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

3D PDB for NP0211462 ((6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

SMILES for NP0211462 ((6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

INCHI for NP0211462 ((6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

Structure for NP0211462 ((6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)

3D Structure for NP0211462 ((6-{[3-(hepta-1,3,5-trien-1-yl)-6-methoxy-5-methyl-1-oxo-3,4-dihydro-2-benzopyran-8-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl acetate)