NP-MRD: Showing NP-Card for 17-hydroxy-3-{[(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(19),3,5,14,16-hexaen-9-one (NP0202814)

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Record Information

Version

2.0

Created at

2022-09-04 22:06:55 UTC

Updated at

2022-09-04 22:06:55 UTC

NP-MRD ID

NP0202814

Secondary Accession Numbers

None

Natural Product Identification

Common Name

17-hydroxy-3-{[(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(19),3,5,14,16-hexaen-9-one

Description

17-Hydroxy-3-{[(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-{[(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(19),3,5,14,16-hexaen-9-one is found in Acer nikoense. Based on a literature review very few articles have been published on 17-hydroxy-3-{[(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


  Mrv1652309052200062D          

 33 36  0  0  1  0            999 V2000
    3.7977    3.2615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1526    2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6202    3.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426    3.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8659    2.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6280    2.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5630    1.1955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0262    0.5129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6666   -0.2296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8438   -0.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2172    0.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7607    1.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3948    0.3474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0399    1.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2175    1.1573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7499    0.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1048   -0.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          2D

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M  END


  Mrv1652309052200062D          

 33 36  0  0  1  0            999 V2000
    3.7977    3.2615    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1526    2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6202    3.1964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4426    3.1314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8659    2.3340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0202814

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@@H](OC2=CC=C3CCC(=O)CCCCC4=CC=C(O)C(=C4)C2=C3)[C@H](O)[C@@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H30O8/c26-13-21-22(29)23(30)24(31)25(33-21)32-20-10-7-15-5-8-16(27)4-2-1-3-14-6-9-19(28)17(11-14)18(20)12-15/h6-7,9-12,21-26,28-31H,1-5,8,13H2/t21-,22-,23+,24-,25-/m1/s1

> <INCHI_KEY>
IUTIZFVLSAZJRT-NHTNDUFYSA-N

> <FORMULA>
C25H30O8

> <MOLECULAR_WEIGHT>
458.507

> <EXACT_MASS>
458.194067926

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
47.46186508746261

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
17-hydroxy-3-{[(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(19),3,5,14,16-hexaen-9-one

> <JCHEM_LOGP>
2.3520149169999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.20160366898087

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.781206271309859

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092346192008

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
119.227

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
17-hydroxy-3-{[(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(19),3,5,14,16-hexaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0       7.089   6.088   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.752   4.698   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.624   5.967   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.159   5.845   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.950   4.357   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.372   3.767   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.251   2.232   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.116   0.957   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.444  -0.429   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.908  -0.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      10.404  -1.995   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       9.739   0.527   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.753   1.873   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.204   0.649   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.541   2.039   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.006   2.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.133   0.891   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.796  -0.499   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.331  -0.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.993  -2.010   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.120  -3.279   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.783  -4.670   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.910  -5.938   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.573  -7.329   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.108  -7.450   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.375  -5.817   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.502  -7.086   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.713  -4.427   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       3.177  -4.305   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.585  -3.158   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       4.923  -1.768   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.344   3.550   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.216   4.819   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   33                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12    7                                                       
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   32                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   21   31                                                  
CONECT   31   30                                                            
CONECT   32   16   33                                                       
CONECT   33   32    2                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₀O₈

Average Mass

458.5070 Da

Monoisotopic Mass

458.19407 Da

IUPAC Name

17-hydroxy-3-{[(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(19),3,5,14,16-hexaen-9-one

Traditional Name

17-hydroxy-3-{[(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(19),3,5,14,16-hexaen-9-one

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@@H](OC2=CC=C3CCC(=O)CCCCC4=CC=C(O)C(=C4)C2=C3)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C25H30O8/c26-13-21-22(29)23(30)24(31)25(33-21)32-20-10-7-15-5-8-16(27)4-2-1-3-14-6-9-19(28)17(11-14)18(20)12-15/h6-7,9-12,21-26,28-31H,1-5,8,13H2/t21-,22-,23+,24-,25-/m1/s1

InChI Key

IUTIZFVLSAZJRT-NHTNDUFYSA-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
Acer nikoense	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
1-hydroxy-2-unsubstituted benzenoid
Monosaccharide
Benzenoid
Oxane
Ketone
Cyclic ketone
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Primary alcohol
Carbonyl group
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	2.35	ChemAxon
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	119.23 m³·mol⁻¹	ChemAxon
Polarizability	47.46 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

162883588

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-{[(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(19),3,5,14,16-hexaen-9-one (NP0202814)

MOL for NP0202814 (17-hydroxy-3-{[(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(19),3,5,14,16-hexaen-9-one)

3D MOL for NP0202814 (17-hydroxy-3-{[(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(19),3,5,14,16-hexaen-9-one)

3D SDF for NP0202814 (17-hydroxy-3-{[(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(19),3,5,14,16-hexaen-9-one)

3D-SDF for NP0202814 (17-hydroxy-3-{[(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(19),3,5,14,16-hexaen-9-one)

PDB for NP0202814 (17-hydroxy-3-{[(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(19),3,5,14,16-hexaen-9-one)

3D PDB for NP0202814 (17-hydroxy-3-{[(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(19),3,5,14,16-hexaen-9-one)

SMILES for NP0202814 (17-hydroxy-3-{[(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(19),3,5,14,16-hexaen-9-one)

INCHI for NP0202814 (17-hydroxy-3-{[(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(19),3,5,14,16-hexaen-9-one)

Structure for NP0202814 (17-hydroxy-3-{[(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(19),3,5,14,16-hexaen-9-one)

3D Structure for NP0202814 (17-hydroxy-3-{[(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(19),3,5,14,16-hexaen-9-one)