NP-MRD: Showing NP-Card for 4-hydroxy-17-methoxy-16-{[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 (NP0293846)

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Record Information

Version

2.0

Created at

2022-09-10 02:05:18 UTC

Updated at

2022-09-10 02:05:19 UTC

NP-MRD ID

NP0293846

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-17-methoxy-16-{[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

Myricatomentoside I 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. Myricatomentoside I is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, myricatomentoside I has been detected, but not quantified in, herbs and spices. 4-hydroxy-17-methoxy-16-{[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 Myrica gale. This could make myricatomentoside I a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061305592D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 05061305592D          

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 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 25 30  1  0  0  0  0
 26 31  1  0  0  0  0
  1 31  1  0  0  0  0
 25 32  1  0  0  0  0
 30 33  1  0  0  0  0
 29 34  1  0  0  0  0
 28 35  1  0  0  0  0
 36 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0293846

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC2OC(CO)C(O)C(O)C2O)C2=CC=C1OC1=CC(CCC(=O)CCCC2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O10/c1-33-25-18-11-8-15(24(25)36-26-23(32)22(31)21(30)20(13-27)35-26)4-2-3-5-16(28)9-6-14-7-10-17(29)19(12-14)34-18/h7-8,10-12,20-23,26-27,29-32H,2-6,9,13H2,1H3

> <INCHI_KEY>
RALVCBWUWHJOGL-UHFFFAOYSA-N

> <FORMULA>
C26H32O10

> <MOLECULAR_WEIGHT>
504.5263

> <EXACT_MASS>
504.199547244

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
50.24174766586586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-hydroxy-18-methoxy-19-{[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

> <ALOGPS_LOGP>
1.22

> <JCHEM_LOGP>
2.0474054723333333

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.200061463379079

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.399757126905072

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923561309846

> <JCHEM_POLAR_SURFACE_AREA>
155.14000000000001

> <JCHEM_REFRACTIVITY>
126.79479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-18-methoxy-19-{[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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       3.767  -1.795   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.732  -2.935   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.227  -2.608   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.191  -3.748   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.314  -3.421   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.349  -4.561   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.854  -4.235   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.323  -2.768   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.288  -1.628   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.362  -0.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.895   0.380   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.513   1.885   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.863   2.076   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.003   1.041   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.298  -0.328   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.793  -0.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.757  -1.141   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.783  -1.955   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.880  -6.028   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.676   2.894   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       3.201  -4.402   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.166  -5.542   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.102   2.464   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.176   1.552   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.246  -3.915   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.741  -3.588   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.706  -4.728   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.175  -6.195   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.680  -6.522   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.716  -5.382   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.272  -2.122   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.282  -2.776   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       9.221  -5.709   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       7.150  -7.989   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       4.140  -7.335   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.609  -8.802   0.000  0.00  0.00           O+0
CONECT    1    2   15   31                                                  
CONECT    2    1    3   21                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   20   23                                                  
CONECT   13   14   24                                                       
CONECT   14   13   15                                                       
CONECT   15    1   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17    3   16                                                       
CONECT   18    5    9                                                       
CONECT   19    6                                                            
CONECT   20   12                                                            
CONECT   21    2   22                                                       
CONECT   22   21                                                            
CONECT   23   12   24                                                       
CONECT   24   13   23                                                       
CONECT   25   26   30   32                                                  
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   35                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   25   33                                                  
CONECT   31   26    1                                                       
CONECT   32   25                                                            
CONECT   33   30                                                            
CONECT   34   29                                                            
CONECT   35   28   36                                                       
CONECT   36   35                                                            
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

504.5263 Da

Monoisotopic Mass

504.19955 Da

IUPAC Name

4-hydroxy-18-methoxy-19-{[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

Traditional Name

4-hydroxy-18-methoxy-19-{[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

CAS Registry Number

Not Available

SMILES

COC1=C(OC2OC(CO)C(O)C(O)C2O)C2=CC=C1OC1=CC(CCC(=O)CCCC2)=CC=C1O

InChI Identifier

InChI=1S/C26H32O10/c1-33-25-18-11-8-15(24(25)36-26-23(32)22(31)21(30)20(13-27)35-26)4-2-3-5-16(28)9-6-14-7-10-17(29)19(12-14)34-18/h7-8,10-12,20-23,26-27,29-32H,2-6,9,13H2,1H3

InChI Key

RALVCBWUWHJOGL-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
Myrica gale	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

Not Available

Substituents

Not Available

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	1.22	ALOGPS
logP	2.05	ChemAxon
logS	-3.2	ALOGPS
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	126.79 m³·mol⁻¹	ChemAxon
Polarizability	50.24 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

HMDB0031536

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008144

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

85261151

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-hydroxy-17-methoxy-16-{[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 (NP0293846)

MOL for NP0293846 (4-hydroxy-17-methoxy-16-{[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 NP0293846 (4-hydroxy-17-methoxy-16-{[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 NP0293846 (4-hydroxy-17-methoxy-16-{[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 NP0293846 (4-hydroxy-17-methoxy-16-{[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 NP0293846 (4-hydroxy-17-methoxy-16-{[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 NP0293846 (4-hydroxy-17-methoxy-16-{[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 NP0293846 (4-hydroxy-17-methoxy-16-{[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 NP0293846 (4-hydroxy-17-methoxy-16-{[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 NP0293846 (4-hydroxy-17-methoxy-16-{[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 NP0293846 (4-hydroxy-17-methoxy-16-{[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)