NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-6-{[(3s)-3-[(1e,3e,5e)-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 (NP0152092)

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Record Information

Version

2.0

Created at

2022-09-02 08:30:32 UTC

Updated at

2022-09-02 08:30:32 UTC

NP-MRD ID

NP0152092

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-6-{[(3s)-3-[(1e,3e,5e)-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

(3S)-3alpha-[(1E,3E,5E)-1,3,5-Heptatrienyl]-5-methyl-6-methoxy-8-[(6-O-acetyl-beta-D-glucopyranosyl)oxy]-3,4-dihydro-1H-2-benzopyran-1-one 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. Based on a literature review very few articles have been published on (3S)-3alpha-[(1E,3E,5E)-1,3,5-Heptatrienyl]-5-methyl-6-methoxy-8-[(6-O-acetyl-beta-D-glucopyranosyl)oxy]-3,4-dihydro-1H-2-benzopyran-1-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022210302D          

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M  END

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M  END


  Mrv1652309022210302D          

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 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  0  0  0  0
 19 31  1  0  0  0  0
 31 32  1  1  0  0  0
 17 33  2  0  0  0  0
 10 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
  8 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0152092

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O[C@@H]2O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]2O)=C2C(=O)O[C@@H](CC2=C1C)\C=C\C=C\C=C\C

> <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/b6-5+,8-7+,10-9+/t16-,20-,22-,23+,24-,26-/m1/s1

> <INCHI_KEY>
HFNVEOAKDZDOHA-FXHUFLIJSA-N

> <FORMULA>
C26H32O10

> <MOLECULAR_WEIGHT>
504.532

> <EXACT_MASS>
504.19954723

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.708650534775586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[(3S)-3-[(1E,3E,5E)-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>
140.98000000000002

> <JCHEM_REFRACTIVITY>
131.31769999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[(3S)-3-[(1E,3E,5E)-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                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -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  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.669  -7.700   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335  -7.700   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  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   36                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   33                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18   33                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   31                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   27                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   21   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   19   32                                                  
CONECT   32   31                                                            
CONECT   33   17   10   34                                                  
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    8                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
(3S)-3a-[(1E,3E,5E)-1,3,5-Heptatrienyl]-5-methyl-6-methoxy-8-[(6-O-acetyl-b-D-glucopyranosyl)oxy]-3,4-dihydro-1H-2-benzopyran-1-one	Generator
(3S)-3Α-[(1E,3E,5E)-1,3,5-heptatrienyl]-5-methyl-6-methoxy-8-[(6-O-acetyl-β-D-glucopyranosyl)oxy]-3,4-dihydro-1H-2-benzopyran-1-one	Generator

Chemical Formula

C₂₆H₃₂O₁₀

Average Mass

504.5320 Da

Monoisotopic Mass

504.19955 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-6-{[(3S)-3-[(1E,3E,5E)-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

[(2R,3S,4S,5R,6S)-6-{[(3S)-3-[(1E,3E,5E)-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(O[C@@H]2O[C@H](COC(C)=O)[C@@H](O)[C@H](O)[C@H]2O)=C2C(=O)O[C@@H](CC2=C1C)\C=C\C=C\C=C\C

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/b6-5+,8-7+,10-9+/t16-,20-,22-,23+,24-,26-/m1/s1

InChI Key

HFNVEOAKDZDOHA-FXHUFLIJSA-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	53.71 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

78440687

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102212907

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-6-{[(3s)-3-[(1e,3e,5e)-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 (NP0152092)

MOL for NP0152092 ([(2r,3s,4s,5r,6s)-6-{[(3s)-3-[(1e,3e,5e)-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 NP0152092 ([(2r,3s,4s,5r,6s)-6-{[(3s)-3-[(1e,3e,5e)-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 NP0152092 ([(2r,3s,4s,5r,6s)-6-{[(3s)-3-[(1e,3e,5e)-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 NP0152092 ([(2r,3s,4s,5r,6s)-6-{[(3s)-3-[(1e,3e,5e)-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 NP0152092 ([(2r,3s,4s,5r,6s)-6-{[(3s)-3-[(1e,3e,5e)-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 NP0152092 ([(2r,3s,4s,5r,6s)-6-{[(3s)-3-[(1e,3e,5e)-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 NP0152092 ([(2r,3s,4s,5r,6s)-6-{[(3s)-3-[(1e,3e,5e)-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 NP0152092 ([(2r,3s,4s,5r,6s)-6-{[(3s)-3-[(1e,3e,5e)-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 NP0152092 ([(2r,3s,4s,5r,6s)-6-{[(3s)-3-[(1e,3e,5e)-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 NP0152092 ([(2r,3s,4s,5r,6s)-6-{[(3s)-3-[(1e,3e,5e)-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)