NP-MRD: Showing NP-Card for Jasminoside (NP0057660)

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Record Information

Version

2.0

Created at

2022-04-28 03:03:44 UTC

Updated at

2022-04-28 03:03:44 UTC

NP-MRD ID

NP0057660

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Jasminoside

Description

(2S,3E,4S)-4-(2-methoxy-2-oxoethyl)-3-(2-{[(2E)-3-phenylprop-2-enoyl]oxy}ethylidene)-2-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid 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. Jasminoside is found in Jasminum humile . Based on a literature review very few articles have been published on (2S,3E,4S)-4-(2-methoxy-2-oxoethyl)-3-(2-{[(2E)-3-phenylprop-2-enoyl]oxy}ethylidene)-2-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205032D          

 39 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282205032D          

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 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
  1 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 16 23  1  1  0  0  0
 24 23  1  6  0  0  0
 24 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
 28 29  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  6  0  0  0
 28 31  1  6  0  0  0
 27 32  1  1  0  0  0
 26 33  1  6  0  0  0
 33 34  1  0  0  0  0
  1 35  1  6  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057660

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1\C(=C/COC(=O)\C=C\C2=CC=CC=C2)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)OC=C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O13/c1-35-20(29)11-16-15(9-10-36-19(28)8-7-14-5-3-2-4-6-14)25(37-13-17(16)24(33)34)39-26-23(32)22(31)21(30)18(12-27)38-26/h2-9,13,16,18,21-23,25-27,30-32H,10-12H2,1H3,(H,33,34)/b8-7+,15-9+/t16-,18+,21+,22-,23-,25-,26-/m0/s1

> <INCHI_KEY>
JGHUOJAZXGSFRI-PCIHGBRHSA-N

> <FORMULA>
C26H30O13

> <MOLECULAR_WEIGHT>
550.513

> <EXACT_MASS>
550.168641026

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
53.614448649885055

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3E,4S)-4-(2-methoxy-2-oxoethyl)-3-(2-{[(2E)-3-phenylprop-2-enoyl]oxy}ethylidene)-2-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid

> <ALOGPS_LOGP>
-0.13

> <JCHEM_LOGP>
0.07916424866666708

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.206586036491277

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.112252711184338

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810849052288777

> <JCHEM_POLAR_SURFACE_AREA>
198.50999999999996

> <JCHEM_REFRACTIVITY>
131.46209999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,5E,6S)-4-(2-methoxy-2-oxoethyl)-5-(2-{[(2E)-3-phenylprop-2-enoyl]oxy}ethylidene)-6-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylic acid

> <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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.335  -0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -10.669   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -10.669   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.532   0.161   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -0.000   1.540   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
CONECT    1    2   19   35                                                  
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    2   17   23                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18    1   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   16   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28   32                                                  
CONECT   28   27   29   31                                                  
CONECT   29   28   24   30                                                  
CONECT   30   29                                                            
CONECT   31   28                                                            
CONECT   32   27                                                            
CONECT   33   26   34                                                       
CONECT   34   33                                                            
CONECT   35    1   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Value	Source
(2S,3E,4S)-4-(2-Methoxy-2-oxoethyl)-3-(2-{[(2E)-3-phenylprop-2-enoyl]oxy}ethylidene)-2-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate	Generator

Chemical Formula

C₂₆H₃₀O₁₃

Average Mass

550.5130 Da

Monoisotopic Mass

550.16864 Da

IUPAC Name

(2S,3E,4S)-4-(2-methoxy-2-oxoethyl)-3-(2-{[(2E)-3-phenylprop-2-enoyl]oxy}ethylidene)-2-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid

Traditional Name

(4S,5E,6S)-4-(2-methoxy-2-oxoethyl)-5-(2-{[(2E)-3-phenylprop-2-enoyl]oxy}ethylidene)-6-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,6-dihydropyran-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1\C(=C/COC(=O)\C=C\C2=CC=CC=C2)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)OC=C1C(O)=O

InChI Identifier

InChI=1S/C26H30O13/c1-35-20(29)11-16-15(9-10-36-19(28)8-7-14-5-3-2-4-6-14)25(37-13-17(16)24(33)34)39-26-23(32)22(31)21(30)18(12-27)38-26/h2-9,13,16,18,21-23,25-27,30-32H,10-12H2,1H3,(H,33,34)/b8-7+,15-9+/t16-,18+,21+,22-,23-,25-,26-/m0/s1

InChI Key

JGHUOJAZXGSFRI-PCIHGBRHSA-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
Jasminum humile	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
Cinnamic acid ester
Cinnamic acid or derivatives
O-glycosyl compound
Secoiridoid-skeleton
Glycosyl compound
Monoterpenoid
Monocyclic monoterpenoid
Aromatic monoterpenoid
Tricarboxylic acid or derivatives
Styrene
Sugar acid
Fatty acid ester
Fatty acyl
Benzenoid
Oxane
Monosaccharide
Monocyclic benzene moiety
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-0.13	ALOGPS
logP	0.079	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.11	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	198.51 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	131.46 m³·mol⁻¹	ChemAxon
Polarizability	53.61 Å³	ChemAxon
Number of Rings	3	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

162953620

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Jasminoside (NP0057660)

MOL for NP0057660 (Jasminoside)

3D MOL for NP0057660 (Jasminoside)

3D SDF for NP0057660 (Jasminoside)

3D-SDF for NP0057660 (Jasminoside)

PDB for NP0057660 (Jasminoside)

3D PDB for NP0057660 (Jasminoside)

SMILES for NP0057660 (Jasminoside)

INCHI for NP0057660 (Jasminoside)

Structure for NP0057660 (Jasminoside)

3D Structure for NP0057660 (Jasminoside)