NP-MRD: Showing NP-Card for 2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0164324)

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Record Information

Version

1.0

Created at

2022-09-02 23:10:50 UTC

Updated at

2022-09-02 23:10:50 UTC

NP-MRD ID

NP0164324

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

2-{[14-Hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. 2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Mikania laevigata. Based on a literature review very few articles have been published on 2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]Hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032201112D          

 34 38  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309032201112D          

 34 38  0  0  0  0            999 V2000
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  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 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
  2 29  1  0  0  0  0
 19 29  1  0  0  0  0
 26 30  1  0  0  0  0
 30 31  1  0  0  0  0
 24 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0164324

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C(CCC2(C)C3CCC4CC3(CC4(O)CO)CCC12)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H44O8/c1-23(2)16-6-9-25-10-14(26(32,12-25)13-28)4-5-17(25)24(16,3)8-7-18(23)34-22-21(31)20(30)19(29)15(11-27)33-22/h14-22,27-32H,4-13H2,1-3H3

> <INCHI_KEY>
TZSJZZXUCLOPQF-UHFFFAOYSA-N

> <FORMULA>
C26H44O8

> <MOLECULAR_WEIGHT>
484.63

> <EXACT_MASS>
484.303618377

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
78

> <JCHEM_AVERAGE_POLARIZABILITY>
53.547968236392975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.81

> <JCHEM_LOGP>
0.6000200719999991

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.091414765209645

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.19623586585305

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835440417778

> <JCHEM_POLAR_SURFACE_AREA>
139.84

> <JCHEM_REFRACTIVITY>
123.0235

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.39e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      10.398   3.756   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.081   2.959   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.525   4.395   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.094   1.799   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.605   2.098   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      12.102   3.555   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.089   4.714   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.586   6.172   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.572   7.331   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.070   8.789   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      13.097   6.470   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.594   7.928   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.110   5.311   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      15.621   5.609   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      13.613   3.853   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.627   2.694   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.597   0.342   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.086   0.044   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.072   1.203   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.574  -0.254   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.544   0.904   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.192  -0.679   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.640  -1.051   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.514   0.113   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.521   1.061   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.401   2.089   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.035   3.549   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.564   3.842   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.570   2.661   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.845   2.718   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.731   1.526   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       0.492   2.441   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       0.307   0.940   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.102  -0.587   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   29                                             
CONECT    3    2                                                            
CONECT    4    2    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   29                                             
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   31                                                  
CONECT   25   24   26                                                       
CONECT   26   25   21   27   30                                             
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    2   19                                                  
CONECT   30   26   31                                                       
CONECT   31   30   24   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₄O₈

Average Mass

484.6300 Da

Monoisotopic Mass

484.30362 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC1(C)C(CCC2(C)C3CCC4CC3(CC4(O)CO)CCC12)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C26H44O8/c1-23(2)16-6-9-25-10-14(26(32,12-25)13-28)4-5-17(25)24(16,3)8-7-18(23)34-22-21(31)20(30)19(29)15(11-27)33-22/h14-22,27-32H,4-13H2,1-3H3

InChI Key

TZSJZZXUCLOPQF-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
Mikania laevigata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Diterpene glycosides

Alternative Parents

Substituents

Diterpene glycoside
Diterpenoid
Kaurane diterpenoid
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monosaccharide
Oxane
Cyclic alcohol
Tertiary alcohol
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Primary alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.81	ALOGPS
logS	-3	ALOGPS

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

163040389

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0164324)

MOL for NP0164324 (2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0164324 (2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0164324 (2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0164324 (2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0164324 (2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0164324 (2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0164324 (2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0164324 (2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0164324 (2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0164324 (2-{[14-hydroxy-14-(hydroxymethyl)-5,5,9-trimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)