NP-MRD: Showing NP-Card for 17-hydroxy-3,4-dimethoxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one (NP0196025)

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Record Information

Version

2.0

Created at

2022-09-04 14:00:34 UTC

Updated at

2022-09-04 14:00:34 UTC

NP-MRD ID

NP0196025

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-hydroxy-3,4-dimethoxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one

Description

17-Hydroxy-3,4-dimethoxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1²,⁶]Nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one belongs to the class of organic compounds known as meta,meta-bridged biphenyls. These are cyclic diarylheptanoids where the two aryl groups are linked to each other by an ether group conjugated to their 3-position. 17-hydroxy-3,4-dimethoxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one is found in Morella rubra. Based on a literature review very few articles have been published on 17-hydroxy-3,4-dimethoxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1²,⁶]Nonadeca-1(17),2,4,6(19),14(18),15-hexaen-9-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042216002D          

 37 40  0  0  1  0            999 V2000
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M  END

     RDKit          2D

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M  END


  Mrv1652309042216002D          

 37 40  0  0  1  0            999 V2000
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  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  1  0  0  0
  7 20  2  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
  6 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 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
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
  4 36  1  0  0  0  0
 36 37  2  0  0  0  0
 31 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196025

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2=CC(=C1OC)C1=CC(CCCCC(=O)CC2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O10/c1-34-25-18-12-15(8-9-16(29)6-4-3-5-14-7-10-19(30)17(18)11-14)24(26(25)35-2)37-27-23(33)22(32)21(31)20(13-28)36-27/h7,10-12,20-23,27-28,30-33H,3-6,8-9,13H2,1-2H3/t20-,21-,22+,23-,27+/m1/s1

> <INCHI_KEY>
SMYOKOPOWMBDGH-YWZYQIPGSA-N

> <FORMULA>
C27H34O10

> <MOLECULAR_WEIGHT>
518.559

> <EXACT_MASS>
518.215197295

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
53.22788640553746

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
17-hydroxy-3,4-dimethoxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1^{2,6}]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one

> <JCHEM_LOGP>
2.0366723856666673

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.20154584333579

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.796920460697851

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092356131003

> <JCHEM_POLAR_SURFACE_AREA>
155.14000000000001

> <JCHEM_REFRACTIVITY>
132.15339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
17-hydroxy-3,4-dimethoxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1^{2,6}]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       7.762   0.163   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.029  -1.191   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.836  -2.503   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.080  -3.767   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.023  -5.164   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.500  -5.600   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.234  -3.671   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.763  -3.494   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      12.375  -2.081   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.457  -0.844   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      12.068   0.569   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.150   1.805   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.761   3.219   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      13.598   0.746   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.210   2.159   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.516  -0.490   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.046  -0.313   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      13.905  -1.904   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.823  -3.140   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.372  -2.395   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.046  -1.010   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.184   0.266   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.541  -7.140   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.090  -7.655   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.223  -9.100   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.000 -10.430   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.684  -9.141   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.878  -7.829   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.339  -7.870   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.533  -6.558   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.267  -5.204   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.462  -3.891   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.195  -2.538   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.735  -2.496   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.469  -1.142   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.540  -3.809   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.807  -5.162   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   36                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   23                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   18                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    9   19                                                  
CONECT   19   18                                                            
CONECT   20    7    3   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23    6   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    4   37                                                  
CONECT   37   36   31                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₄O₁₀

Average Mass

518.5590 Da

Monoisotopic Mass

518.21520 Da

IUPAC Name

17-hydroxy-3,4-dimethoxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1^{2,6}]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one

Traditional Name

17-hydroxy-3,4-dimethoxy-5-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1^{2,6}]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one

CAS Registry Number

Not Available

SMILES

COC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2=CC(=C1OC)C1=CC(CCCCC(=O)CC2)=CC=C1O

InChI Identifier

InChI=1S/C27H34O10/c1-34-25-18-12-15(8-9-16(29)6-4-3-5-14-7-10-19(30)17(18)11-14)24(26(25)35-2)37-27-23(33)22(32)21(31)20(13-28)36-27/h7,10-12,20-23,27-28,30-33H,3-6,8-9,13H2,1-2H3/t20-,21-,22+,23-,27+/m1/s1

InChI Key

SMYOKOPOWMBDGH-YWZYQIPGSA-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
Morella rubra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as meta,meta-bridged biphenyls. These are cyclic diarylheptanoids where the two aryl groups are linked to each other by an ether group conjugated to their 3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Cyclic diarylheptanoids

Direct Parent

Meta,meta-bridged biphenyls

Alternative Parents

Substituents

Meta,meta-bridged biphenyl
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monosaccharide
Oxane
Benzenoid
Ketone
Secondary alcohol
Cyclic ketone
Polyol
Organoheterocyclic compound
Acetal
Oxacycle
Ether
Primary alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen 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	2.04	ChemAxon
pKa (Strongest Acidic)	9.8	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	155.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	132.15 m³·mol⁻¹	ChemAxon
Polarizability	53.23 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

162891558

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 17-hydroxy-3,4-dimethoxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one (NP0196025)

MOL for NP0196025 (17-hydroxy-3,4-dimethoxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one)

3D MOL for NP0196025 (17-hydroxy-3,4-dimethoxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one)

3D SDF for NP0196025 (17-hydroxy-3,4-dimethoxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one)

3D-SDF for NP0196025 (17-hydroxy-3,4-dimethoxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one)

PDB for NP0196025 (17-hydroxy-3,4-dimethoxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one)

3D PDB for NP0196025 (17-hydroxy-3,4-dimethoxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one)

SMILES for NP0196025 (17-hydroxy-3,4-dimethoxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one)

INCHI for NP0196025 (17-hydroxy-3,4-dimethoxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one)

Structure for NP0196025 (17-hydroxy-3,4-dimethoxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one)

3D Structure for NP0196025 (17-hydroxy-3,4-dimethoxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tricyclo[12.3.1.1²,⁶]nonadeca-1(18),2,4,6(19),14,16-hexaen-9-one)