NP-MRD: Showing NP-Card for (9s)-4-hydroxy-18-methoxy-9-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one (NP0247945)

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Record Information

Version

2.0

Created at

2022-09-07 09:58:48 UTC

Updated at

2022-09-07 09:58:48 UTC

NP-MRD ID

NP0247945

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9s)-4-hydroxy-18-methoxy-9-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one

Description

(9S)-4-hydroxy-17-methoxy-9-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1³,⁷]Icosa-1(17),3,5,7(20),15,18-hexaen-10-one belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. (9s)-4-hydroxy-18-methoxy-9-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one is found in Juglans mandshurica. Based on a literature review very few articles have been published on (9S)-4-hydroxy-17-methoxy-9-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1³,⁷]Icosa-1(17),3,5,7(20),15,18-hexaen-10-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072211582D          

 36 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309072211582D          

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 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  1  1  0  0  0
 18 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
  5 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0247945

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=CC=C1OC1=CC(C[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(=O)CCCC2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O10/c1-33-21-10-14-4-2-3-5-16(28)20(35-26-25(32)24(31)23(30)22(13-27)36-26)12-15-6-8-17(29)19(11-15)34-18(21)9-7-14/h6-11,20,22-27,29-32H,2-5,12-13H2,1H3/t20-,22+,23+,24-,25+,26+/m0/s1

> <INCHI_KEY>
XOARHNDBVGTEHH-USBIVESDSA-N

> <FORMULA>
C26H32O10

> <MOLECULAR_WEIGHT>
504.532

> <EXACT_MASS>
504.19954723

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
50.19547628604241

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9S)-4-hydroxy-18-methoxy-9-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1^{3,7}]icosa-1(17),3(20),4,6,15,18-hexaen-10-one

> <JCHEM_LOGP>
1.9771373209999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.209986223678278

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.400445248461173

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810836995636087

> <JCHEM_POLAR_SURFACE_AREA>
155.14000000000001

> <JCHEM_REFRACTIVITY>
126.575

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(9S)-4-hydroxy-18-methoxy-9-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1^{3,7}]icosa-1(17),3(20),4,6,15,18-hexaen-10-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       9.857   0.629   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.034   1.621   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.764   3.138   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.971   4.133   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.744   5.701   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.268   6.192   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.082   5.218   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.252   3.667   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.612   3.463   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.018   3.803   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.054   5.370   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.758   6.253   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.375   5.526   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.285   3.977   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.590   3.120   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.485   1.584   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.973   7.824   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.771   9.172   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.668  10.247   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.185   9.829   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.806   8.336   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.324   7.918   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.945   6.426   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.048   5.351   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.221   8.993   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.261   8.575   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.600  10.485   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.503  11.560   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.082  10.904   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.461  12.396   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       7.100  10.007   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.576  11.454   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.661  10.219   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.179   9.750   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.386   8.716   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.079   7.278   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   36                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10   16                                                  
CONECT   16   15                                                            
CONECT   17   12   18                                                       
CONECT   18   17   19   31                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   20   30                                                  
CONECT   30   29                                                            
CONECT   31   18   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35    5                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₁₀

Average Mass

504.5320 Da

Monoisotopic Mass

504.19955 Da

IUPAC Name

(9S)-4-hydroxy-18-methoxy-9-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1^{3,7}]icosa-1(17),3(20),4,6,15,18-hexaen-10-one

Traditional Name

(9S)-4-hydroxy-18-methoxy-9-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1^{3,7}]icosa-1(17),3(20),4,6,15,18-hexaen-10-one

CAS Registry Number

Not Available

SMILES

COC1=CC2=CC=C1OC1=CC(C[C@H](O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C(=O)CCCC2)=CC=C1O

InChI Identifier

InChI=1S/C26H32O10/c1-33-21-10-14-4-2-3-5-16(28)20(35-26-25(32)24(31)23(30)22(13-27)36-26)12-15-6-8-17(29)19(11-15)34-18(21)9-7-14/h6-11,20,22-27,29-32H,2-5,12-13H2,1H3/t20-,22+,23+,24-,25+,26+/m0/s1

InChI Key

XOARHNDBVGTEHH-USBIVESDSA-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
Juglans mandshurica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Meta,para-diphenylether diarylheptanoid
Hexose monosaccharide
Diaryl ether
Glycosyl compound
O-glycosyl compound
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxane
Monosaccharide
Cyclic ketone
Secondary alcohol
Ketone
Acetal
Ether
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
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	1.98	ChemAxon
pKa (Strongest Acidic)	8.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	126.58 m³·mol⁻¹	ChemAxon
Polarizability	50.2 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

163045431

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (9s)-4-hydroxy-18-methoxy-9-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one (NP0247945)

MOL for NP0247945 ((9s)-4-hydroxy-18-methoxy-9-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one)

3D MOL for NP0247945 ((9s)-4-hydroxy-18-methoxy-9-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one)

3D SDF for NP0247945 ((9s)-4-hydroxy-18-methoxy-9-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one)

3D-SDF for NP0247945 ((9s)-4-hydroxy-18-methoxy-9-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one)

PDB for NP0247945 ((9s)-4-hydroxy-18-methoxy-9-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one)

3D PDB for NP0247945 ((9s)-4-hydroxy-18-methoxy-9-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one)

SMILES for NP0247945 ((9s)-4-hydroxy-18-methoxy-9-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one)

INCHI for NP0247945 ((9s)-4-hydroxy-18-methoxy-9-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one)

Structure for NP0247945 ((9s)-4-hydroxy-18-methoxy-9-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one)

3D Structure for NP0247945 ((9s)-4-hydroxy-18-methoxy-9-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-oxatricyclo[13.2.2.1³,⁷]icosa-1(17),3(20),4,6,15,18-hexaen-10-one)