NP-MRD: Showing NP-Card for 3beta-Hydroxysolanascone beta-sophoroside (NP0064954)

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Record Information

Version

2.0

Created at

2022-04-28 09:15:19 UTC

Updated at

2022-04-28 09:15:20 UTC

NP-MRD ID

NP0064954

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3beta-Hydroxysolanascone beta-sophoroside

Description

(1S,4R,5S,7S,9R,10S,11S)-9-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5,10,11-trimethyltetracyclo[5.3.1.1¹,⁴.0⁵,¹¹]Dodecan-8-one belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. 3beta-Hydroxysolanascone beta-sophoroside is found in Nicotiana tabacum . Based on a literature review very few articles have been published on (1S,4R,5S,7S,9R,10S,11S)-9-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5,10,11-trimethyltetracyclo[5.3.1.1¹,⁴.0⁵,¹¹]Dodecan-8-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282211152D          

 39 44  0  0  1  0            999 V2000
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 30 39  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282211152D          

 39 44  0  0  1  0            999 V2000
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   -1.2720   -2.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7008   -2.3753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4222   -2.7755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7292   -4.0251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3147   -4.8746    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1283   -4.0744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1140   -4.8992    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8213   -5.3240    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8071   -6.1489    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0856   -6.5490    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6217   -6.1242    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6074   -5.2994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3431   -6.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3574   -7.3492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0714   -7.3739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5143   -6.5736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5428   -4.9239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  5 12  1  0  0  0  0
 10 13  1  1  0  0  0
  5 13  1  1  0  0  0
  9 14  1  6  0  0  0
  6 15  1  6  0  0  0
  4 16  1  6  0  0  0
  3 17  1  1  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 18 23  1  0  0  0  0
 22 24  1  1  0  0  0
 24 25  1  0  0  0  0
 21 26  1  6  0  0  0
 20 27  1  1  0  0  0
 19 28  1  6  0  0  0
 29 28  1  1  0  0  0
 29 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
 33 34  1  0  0  0  0
 29 34  1  0  0  0  0
 33 35  1  1  0  0  0
 35 36  1  0  0  0  0
 32 37  1  6  0  0  0
 31 38  1  1  0  0  0
 30 39  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0064954

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)[C@H]2C[C@@]3(C)[C@@H]4CC[C@@]1(C4)[C@@]23C

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O12/c1-10-21(15(30)12-7-25(2)11-4-5-27(10,6-11)26(12,25)3)38-24-22(19(34)17(32)14(9-29)37-24)39-23-20(35)18(33)16(31)13(8-28)36-23/h10-14,16-24,28-29,31-35H,4-9H2,1-3H3/t10-,11-,12-,13-,14-,16-,17-,18+,19+,20-,21-,22-,23+,24+,25+,26+,27+/m1/s1

> <INCHI_KEY>
KZKUQDVDJRRNRJ-WGZBLJFHSA-N

> <FORMULA>
C27H42O12

> <MOLECULAR_WEIGHT>
558.621

> <EXACT_MASS>
558.267626792

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
57.06380913587573

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4R,5S,7S,9R,10S,11S)-9-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5,10,11-trimethyltetracyclo[5.3.1.1^{1,4}.0^{5,11}]dodecan-8-one

> <ALOGPS_LOGP>
-0.65

> <JCHEM_LOGP>
-1.3595438053333337

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.70060669809499

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.089848422498955

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083576687354

> <JCHEM_POLAR_SURFACE_AREA>
195.6

> <JCHEM_REFRACTIVITY>
129.82539999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,5S,7S,9R,10S,11S)-9-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-5,10,11-trimethyltetracyclo[5.3.1.1^{1,4}.0^{5,11}]dodecan-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -0.993  -2.149   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.357  -2.865   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.319  -2.986   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.689  -2.178   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.933  -0.534   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.529  -0.043   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.935  -0.570   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.196   0.997   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.395   1.418   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.081   1.745   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.850   0.765   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.442  -0.815   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.911   1.092   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.051   2.919   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.536  -1.583   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.966  -3.038   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.293  -4.526   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.054  -5.273   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.081  -6.813   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.428  -7.560   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.748  -6.767   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.721  -5.227   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.374  -4.480   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -5.041  -4.434   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -6.388  -5.181   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -5.095  -7.514   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -2.454  -9.099   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.239  -7.605   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.213  -9.145   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.533  -9.938   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.507 -11.478   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.160 -12.225   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.160 -11.432   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.134  -9.892   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.507 -12.179   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.534 -13.719   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.133 -13.765   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       2.827 -12.271   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       2.880  -9.191   0.000  0.00  0.00           O+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4   17                                                  
CONECT    4    3    5   16                                                  
CONECT    5    4    6   12   13                                             
CONECT    6    5    7    9   15                                             
CONECT    7    6    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8    6   10   14                                             
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    5                                                       
CONECT   13   10    5                                                       
CONECT   14    9                                                            
CONECT   15    6                                                            
CONECT   16    4                                                            
CONECT   17    3   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20   28                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   18                                                       
CONECT   24   22   25                                                       
CONECT   25   24                                                            
CONECT   26   21                                                            
CONECT   27   20                                                            
CONECT   28   19   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31   39                                                  
CONECT   31   30   32   38                                                  
CONECT   32   31   33   37                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33   29                                                       
CONECT   35   33   36                                                       
CONECT   36   35                                                            
CONECT   37   32                                                            
CONECT   38   31                                                            
CONECT   39   30                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₄₂O₁₂

Average Mass

558.6210 Da

Monoisotopic Mass

558.26763 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C(=O)[C@H]2C[C@@]3(C)[C@@H]4CC[C@@]1(C4)[C@@]23C

InChI Identifier

InChI=1S/C27H42O12/c1-10-21(15(30)12-7-25(2)11-4-5-27(10,6-11)26(12,25)3)38-24-22(19(34)17(32)14(9-29)37-24)39-23-20(35)18(33)16(31)13(8-28)36-23/h10-14,16-24,28-29,31-35H,4-9H2,1-3H3/t10-,11-,12-,13-,14-,16-,17-,18+,19+,20-,21-,22-,23+,24+,25+,26+,27+/m1/s1

InChI Key

KZKUQDVDJRRNRJ-WGZBLJFHSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Nicotiana tabacum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Spirovetivane-type sesquiterpenoid
Sesquiterpenoid
Disaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Ketone
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Polyol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
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	-0.65	ALOGPS
logP	-1.4	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.09	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	195.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	129.83 m³·mol⁻¹	ChemAxon
Polarizability	57.06 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

163090706

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3beta-Hydroxysolanascone beta-sophoroside (NP0064954)

MOL for NP0064954 (3beta-Hydroxysolanascone beta-sophoroside)

3D MOL for NP0064954 (3beta-Hydroxysolanascone beta-sophoroside)

3D SDF for NP0064954 (3beta-Hydroxysolanascone beta-sophoroside)

3D-SDF for NP0064954 (3beta-Hydroxysolanascone beta-sophoroside)

PDB for NP0064954 (3beta-Hydroxysolanascone beta-sophoroside)

3D PDB for NP0064954 (3beta-Hydroxysolanascone beta-sophoroside)

SMILES for NP0064954 (3beta-Hydroxysolanascone beta-sophoroside)

INCHI for NP0064954 (3beta-Hydroxysolanascone beta-sophoroside)

Structure for NP0064954 (3beta-Hydroxysolanascone beta-sophoroside)

3D Structure for NP0064954 (3beta-Hydroxysolanascone beta-sophoroside)