NP-MRD: Showing NP-Card for [(1r,2s,3s,5s,6r,8s)-6-methoxy-8-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl benzoate (NP0301590)

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Record Information

Version

2.0

Created at

2022-09-10 14:39:28 UTC

Updated at

2022-09-10 14:39:28 UTC

NP-MRD ID

NP0301590

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,2s,3s,5s,6r,8s)-6-methoxy-8-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl benzoate

Description

4-O-methylpaeoniflorin belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. [(1r,2s,3s,5s,6r,8s)-6-methoxy-8-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl benzoate is found in Paeonia lactiflora. [(1r,2s,3s,5s,6r,8s)-6-methoxy-8-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl benzoate was first documented in 2017 (PMID: 28468284). Based on a literature review very few articles have been published on 4-O-methylpaeoniflorin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102216392D          

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M  END

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M  END


  Mrv1652309102216392D          

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 32 34  1  0  0  0  0
 25 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0301590

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@]12C[C@]3(C)O[C@H](O1)[C@]1(COC(=O)C4=CC=CC=C4)[C@@H]2C[C@@]31O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O11/c1-21-10-23(30-2)14-8-24(21,33-19-17(28)16(27)15(26)13(9-25)32-19)22(14,20(34-21)35-23)11-31-18(29)12-6-4-3-5-7-12/h3-7,13-17,19-20,25-28H,8-11H2,1-2H3/t13-,14+,15-,16+,17-,19+,20-,21+,22+,23-,24-/m1/s1

> <INCHI_KEY>
HBUSZOJOEGAJCJ-PHWFTUJASA-N

> <FORMULA>
C24H30O11

> <MOLECULAR_WEIGHT>
494.493

> <EXACT_MASS>
494.178811786

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
37.94415814745207

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2S,3S,5S,6R,8S)-6-methoxy-8-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0^{2,5}.0^{3,8}]decan-2-yl]methyl benzoate

> <JCHEM_LOGP>
0.25657652833333433

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.199865378979762

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.209985046978558

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810836893347306

> <JCHEM_POLAR_SURFACE_AREA>
153.37

> <JCHEM_REFRACTIVITY>
114.05490000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2S,3S,5S,6R,8S)-6-methoxy-8-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0^{2,5}.0^{3,8}]decan-2-yl]methyl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       4.930   4.637   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.969   3.331   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.251   1.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.762   0.987   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.424  -0.621   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.174  -1.142   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.608  -2.184   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.158  -1.596   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.590   0.054   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.584  -1.184   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.388  -2.363   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.340  -3.969   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.651  -4.778   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.007  -4.048   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.605  -6.318   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.915  -7.127   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.869  -8.666   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.513  -9.396   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.203  -8.587   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.249  -7.048   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.905   0.624   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.840  -0.259   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.632  -0.388   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.575   1.229   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.537   2.044   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.756   3.569   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.545   4.520   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.764   6.045   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.553   6.996   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.115   3.948   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.095   4.899   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -0.103   2.423   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -1.533   1.850   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.108   1.472   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.889  -0.053   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9   21                                             
CONECT    4    3    5                                                       
CONECT    5    4    6    7   23                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11   21   23                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21   10    3   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22    5   10   24                                             
CONECT   24   23   25                                                       
CONECT   25   24   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   27   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   25   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₀O₁₁

Average Mass

494.4930 Da

Monoisotopic Mass

494.17881 Da

IUPAC Name

[(1R,2S,3S,5S,6R,8S)-6-methoxy-8-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0^{2,5}.0^{3,8}]decan-2-yl]methyl benzoate

Traditional Name

[(1R,2S,3S,5S,6R,8S)-6-methoxy-8-methyl-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0^{2,5}.0^{3,8}]decan-2-yl]methyl benzoate

CAS Registry Number

Not Available

SMILES

CO[C@]12C[C@]3(C)O[C@H](O1)[C@]1(COC(=O)C4=CC=CC=C4)[C@@H]2C[C@@]31O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C24H30O11/c1-21-10-23(30-2)14-8-24(21,33-19-17(28)16(27)15(26)13(9-25)32-19)22(14,20(34-21)35-23)11-31-18(29)12-6-4-3-5-7-12/h3-7,13-17,19-20,25-28H,8-11H2,1-2H3/t13-,14+,15-,16+,17-,19+,20-,21+,22+,23-,24-/m1/s1

InChI Key

HBUSZOJOEGAJCJ-PHWFTUJASA-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
Paeonia lactiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Aromatic monoterpenoid
Benzoate ester
Pinane monoterpenoid
Nopinane monoterpenoid
Monoterpenoid
Benzoic acid or derivatives
Benzoyl
Furofuran
Oxepane
Ketal
Monocyclic benzene moiety
Oxane
Meta-dioxane
Monosaccharide
Benzenoid
Oxolane
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Primary alcohol
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	0.26	ChemAxon
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	153.37 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	114.05 m³·mol⁻¹	ChemAxon
Polarizability	37.94 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

24656755

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46882921

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bi X, Han L, Qu T, Mu Y, Guan P, Qu X, Wang Z, Huang X: Anti-Inflammatory Effects, SAR, and Action Mechanism of Monoterpenoids from Radix Paeoniae Alba on LPS-Stimulated RAW 264.7 Cells. Molecules. 2017 Apr 29;22(5):715. doi: 10.3390/molecules22050715. [PubMed:28468284 ]
LOTUS database [Link]

Showing NP-Card for [(1r,2s,3s,5s,6r,8s)-6-methoxy-8-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl benzoate (NP0301590)

MOL for NP0301590 ([(1r,2s,3s,5s,6r,8s)-6-methoxy-8-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl benzoate)

3D MOL for NP0301590 ([(1r,2s,3s,5s,6r,8s)-6-methoxy-8-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl benzoate)

3D SDF for NP0301590 ([(1r,2s,3s,5s,6r,8s)-6-methoxy-8-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl benzoate)

3D-SDF for NP0301590 ([(1r,2s,3s,5s,6r,8s)-6-methoxy-8-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl benzoate)

PDB for NP0301590 ([(1r,2s,3s,5s,6r,8s)-6-methoxy-8-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl benzoate)

3D PDB for NP0301590 ([(1r,2s,3s,5s,6r,8s)-6-methoxy-8-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl benzoate)

SMILES for NP0301590 ([(1r,2s,3s,5s,6r,8s)-6-methoxy-8-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl benzoate)

INCHI for NP0301590 ([(1r,2s,3s,5s,6r,8s)-6-methoxy-8-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl benzoate)

Structure for NP0301590 ([(1r,2s,3s,5s,6r,8s)-6-methoxy-8-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl benzoate)

3D Structure for NP0301590 ([(1r,2s,3s,5s,6r,8s)-6-methoxy-8-methyl-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-9,10-dioxatetracyclo[4.3.1.0²,⁵.0³,⁸]decan-2-yl]methyl benzoate)