NP-MRD: Showing NP-Card for 2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-decahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0326644)

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Record Information

Version

2.0

Created at

2022-09-12 08:24:23 UTC

Updated at

2022-09-12 08:24:24 UTC

NP-MRD ID

NP0326644

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-decahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Description

2-{[7-Ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-tetradecahydrophenanthren-9-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-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-decahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol is found in Aster auriculatus. Based on a literature review very few articles have been published on 2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-tetradecahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122210242D          

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M  END

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M  END


  Mrv1652309122210242D          

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    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  3 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 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
 21 23  1  0  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 26 33  1  0  0  0  0
  8 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326644

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CCCC2(CO)C1CC(OC1OC(CO)C(O)C(O)C1O)C1(O)CC(C)(CC(O)C21)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C26H44O9/c1-5-24(4)10-14(29)21-25(13-28)8-6-7-23(2,3)16(25)9-17(26(21,33)12-24)35-22-20(32)19(31)18(30)15(11-27)34-22/h5,14-22,27-33H,1,6-13H2,2-4H3

> <INCHI_KEY>
KXHQDUOYXAVCKN-UHFFFAOYSA-N

> <FORMULA>
C26H44O9

> <MOLECULAR_WEIGHT>
500.629

> <EXACT_MASS>
500.298532997

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
53.987749169173895

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-tetradecahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_LOGP>
-0.42785424300000047

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.034593385064849

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.186898629642764

> <JCHEM_PKA_STRONGEST_BASIC>
-2.762702436776901

> <JCHEM_POLAR_SURFACE_AREA>
160.07

> <JCHEM_REFRACTIVITY>
126.49289999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-decahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      10.121   1.233   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.673   1.760   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.673  -0.220   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       4.414   3.437   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.954  -1.897   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.184  -3.231   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.414  -4.565   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.184  -5.898   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.414  -7.232   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.184  -8.566   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.724  -8.566   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.874  -7.232   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.104  -8.566   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.104  -5.898   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.564  -5.898   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       2.874  -4.565   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.104  -3.231   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.831  -2.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.883  -1.090   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       2.874   3.437   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   11                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   33                                                  
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9    3                                                       
CONECT   12    9   13   25                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   14   24                                                  
CONECT   24   23                                                            
CONECT   25   12   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   26    8   34                                             
CONECT   34   33   35                                                       
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₄O₉

Average Mass

500.6290 Da

Monoisotopic Mass

500.29853 Da

IUPAC Name

2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-tetradecahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-decahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

CC1(C)CCCC2(CO)C1CC(OC1OC(CO)C(O)C(O)C1O)C1(O)CC(C)(CC(O)C21)C=C

InChI Identifier

InChI=1S/C26H44O9/c1-5-24(4)10-14(29)21-25(13-28)8-6-7-23(2,3)16(25)9-17(26(21,33)12-24)35-22-20(32)19(31)18(30)15(11-27)34-22/h5,14-22,27-33H,1,6-13H2,2-4H3

InChI Key

KXHQDUOYXAVCKN-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
Aster auriculatus	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
Pimarane diterpenoid
Hydrophenanthrene
Phenanthrene
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Monosaccharide
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Organoheterocyclic compound
Acetal
Oxacycle
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	-0.43	ChemAxon
pKa (Strongest Acidic)	12.19	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	160.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.49 m³·mol⁻¹	ChemAxon
Polarizability	53.99 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

162962753

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-decahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol (NP0326644)

MOL for NP0326644 (2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-decahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0326644 (2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-decahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0326644 (2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-decahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0326644 (2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-decahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0326644 (2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-decahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0326644 (2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-decahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0326644 (2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-decahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0326644 (2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-decahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0326644 (2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-decahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0326644 (2-{[7-ethenyl-5,8a-dihydroxy-4a-(hydroxymethyl)-1,1,7-trimethyl-decahydrophenanthren-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol)