NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4ar,7s,8as,10as)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate (NP0287977)

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Record Information

Version

2.0

Created at

2022-09-09 17:29:21 UTC

Updated at

2022-09-09 17:29:22 UTC

NP-MRD ID

NP0287977

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4ar,7s,8as,10as)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate

Description

Sumogaside belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. (2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4ar,7s,8as,10as)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate is found in Eleutherococcus koreanus and Eleutherococcus senticosus. (2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4ar,7s,8as,10as)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate was first documented in 2003 (PMID: 12736467). Based on a literature review very few articles have been published on Sumogaside (PMID: 15476312).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092219292D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309092219292D          

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    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  1  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
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  6  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  1  0  0  0
 14 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
  9 33  1  0  0  0  0
 13 33  1  0  0  0  0
 33 34  1  6  0  0  0
 10 35  1  0  0  0  0
  2 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0287977

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]1(CC=C2[C@@H](CC[C@@H]3[C@@](C)(CCC[C@@]23C)C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C1)C(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C26H42O9/c1-24(18(29)13-28)10-7-15-14(11-24)5-6-17-25(15,2)8-4-9-26(17,3)23(33)35-22-21(32)20(31)19(30)16(12-27)34-22/h7,14,16-22,27-32H,4-6,8-13H2,1-3H3/t14-,16+,17-,18?,19+,20-,21+,22-,24-,25-,26+/m0/s1

> <INCHI_KEY>
QTMFSBGINUKCNZ-OJESHDRZSA-N

> <FORMULA>
C26H42O9

> <MOLECULAR_WEIGHT>
498.613

> <EXACT_MASS>
498.282882932

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
52.75328623160783

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4aR,7S,8aS,10aS)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-1-carboxylate

> <JCHEM_LOGP>
0.7474297083333341

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.119858544338204

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.186952408777808

> <JCHEM_PKA_STRONGEST_BASIC>
-2.943540259102936

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
125.85810000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1R,4aR,7S,8aS,10aS)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2H-phenanthrene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       8.673   1.760   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.673  -0.220   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.406  -1.736   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      10.121   0.307   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      11.300  -0.683   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.414  -1.897   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.831  -2.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.883  -1.090   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.063  -0.100   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.151  -2.607   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.598  -3.134   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.865  -4.650   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.313  -5.177   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.580  -6.694   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.027  -7.220   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.492  -4.187   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.939  -4.714   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -5.225  -2.671   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -6.405  -1.681   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.778  -2.144   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.510  -0.627   0.000  0.00  0.00           O+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  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   35                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5                                                            
CONECT    7    2    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   33                                                  
CONECT   10    9   11   35                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   33                                                  
CONECT   14   13   15   16   30                                             
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   19   29                                                  
CONECT   29   28                                                            
CONECT   30   14   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32    9   13   34                                             
CONECT   34   33                                                            
CONECT   35   10    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₄₂O₉

Average Mass

498.6130 Da

Monoisotopic Mass

498.28288 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@]1(CC=C2[C@@H](CC[C@@H]3[C@@](C)(CCC[C@@]23C)C(=O)O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C1)C(O)CO

InChI Identifier

InChI=1S/C26H42O9/c1-24(18(29)13-28)10-7-15-14(11-24)5-6-17-25(15,2)8-4-9-26(17,3)23(33)35-22-21(32)20(31)19(30)16(12-27)34-22/h7,14,16-22,27-32H,4-6,8-13H2,1-3H3/t14-,16+,17-,18?,19+,20-,21+,22-,24-,25-,26+/m0/s1

InChI Key

QTMFSBGINUKCNZ-OJESHDRZSA-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
Eleutherococcus koreanus	LOTUS Database	35616633
Eleutherococcus senticosus	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
Abietane diterpenoid
Diterpenoid
Pimarane diterpenoid
Hydrophenanthrene
Phenanthrene
Hexose monosaccharide
Oxane
Monosaccharide
Carboxylic acid ester
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Carbonyl group
Primary alcohol
Alcohol
Organic oxygen compound
Organooxygen compound
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00032266

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

101239211

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Cai XF, Shen G, Dat NT, Kang OH, Kim JA, Lee YM, Lee JJ, Kim YH: Inhibitory effect of TNF-alpha and IL-8 secretion by pimarane-type diterpenoids from Acanthopanax koreanum. Chem Pharm Bull (Tokyo). 2003 May;51(5):605-7. doi: 10.1248/cpb.51.605. [PubMed:12736467 ]
Cai XF, Lee IS, Dat NT, Shen G, Kim YH: Diterpenoids with inhibitory activity against NFAT transcription factor from Acanthopanax koreanum. Phytother Res. 2004 Aug;18(8):677-80. doi: 10.1002/ptr.1523. [PubMed:15476312 ]
LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4ar,7s,8as,10as)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate (NP0287977)

MOL for NP0287977 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4ar,7s,8as,10as)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

3D MOL for NP0287977 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4ar,7s,8as,10as)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

3D SDF for NP0287977 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4ar,7s,8as,10as)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

3D-SDF for NP0287977 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4ar,7s,8as,10as)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

PDB for NP0287977 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4ar,7s,8as,10as)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

3D PDB for NP0287977 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4ar,7s,8as,10as)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

SMILES for NP0287977 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4ar,7s,8as,10as)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

INCHI for NP0287977 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4ar,7s,8as,10as)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

Structure for NP0287977 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4ar,7s,8as,10as)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)

3D Structure for NP0287977 ((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl (1r,4ar,7s,8as,10as)-7-(1,2-dihydroxyethyl)-1,4a,7-trimethyl-3,4,6,8,8a,9,10,10a-octahydro-2h-phenanthrene-1-carboxylate)