NP-MRD: Showing NP-Card for Steviolmonoside (NP0073954)

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Record Information

Version

2.0

Created at

2022-04-28 19:10:00 UTC

Updated at

2022-04-28 19:10:00 UTC

NP-MRD ID

NP0073954

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Steviolmonoside

Description

Steviolmonoside, also known as glucosilsteviol, belongs to the class of organic compounds known as steviol glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically linked to a steviol (a diterpenoid based on a 13-Hydroxykaur-16-en-18-oic acid) moiety. Steviolmonoside is found in Rubus chingii and Stevia rebaudiana . Steviolmonoside was first documented in 2002 (PMID: 12436720). Based on a literature review a small amount of articles have been published on steviolmonoside (PMID: 15610349) (PMID: 34699718) (PMID: 21477883).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282221102D          

 34 38  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652304282221102D          

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  5 30  1  1  0  0  0
  3 31  1  6  0  0  0
  3 32  1  1  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0073954

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12CCC[C@](C)([C@H]1CC[C@@]13CC(=C)[C@@](C1)(CC[C@@H]23)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H40O8/c1-14-11-25-9-5-16-23(2,7-4-8-24(16,3)22(31)32)17(25)6-10-26(14,13-25)34-21-20(30)19(29)18(28)15(12-27)33-21/h15-21,27-30H,1,4-13H2,2-3H3,(H,31,32)/t15-,16+,17+,18-,19+,20-,21+,23-,24-,25-,26+/m1/s1

> <INCHI_KEY>
QSIDJGUAAUSPMG-CULFPKEHSA-N

> <FORMULA>
C26H40O8

> <MOLECULAR_WEIGHT>
480.598

> <EXACT_MASS>
480.272318248

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
51.59615231088918

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4S,5R,9S,10R,13S)-5,9-dimethyl-14-methylidene-13-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

> <ALOGPS_LOGP>
1.02

> <JCHEM_LOGP>
1.8776953536666663

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.209618198350437

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.590477839773454

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083854595205

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
121.30499999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4S,5R,9S,10R,13S)-5,9-dimethyl-14-methylidene-13-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-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       6.193   2.670   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.658   1.202   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.618   0.065   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.115   0.397   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.650   1.866   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.690   3.002   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.118   2.243   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.999   1.022   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.569  -0.447   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.080  -0.758   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.112   2.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.964   2.885   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.081   4.116   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.659   3.819   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.675   1.439   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.193   1.177   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.512   0.307   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.252   3.730   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.164   5.267   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.452   6.112   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.364   7.650   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.989   8.342   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.701   7.498   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.789   5.960   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.499   5.115   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.674   8.190   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -1.901   9.880   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -4.652   8.494   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -4.564  10.032   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.203   3.340   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.718  -1.013   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.339  -1.449   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.511  -2.448   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       3.888  -1.964   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   31   32                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   30                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   17                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12                                                       
CONECT   12   11   13   15   18                                             
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    8                                                       
CONECT   18   12   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23   27                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   19   25                                                  
CONECT   25   24                                                            
CONECT   26   23                                                            
CONECT   27   22                                                            
CONECT   28   21   29                                                       
CONECT   29   28                                                            
CONECT   30    5                                                            
CONECT   31    3                                                            
CONECT   32    3   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Value	Source
13-O-beta-D-Glucopyranosyl steviol	ChEBI
Glucosilsteviol	ChEBI
Steviol-13-O-D-glucopyranoside	ChEBI
13-O-b-D-Glucopyranosyl steviol	Generator
13-O-Β-D-glucopyranosyl steviol	Generator

Chemical Formula

C₂₆H₄₀O₈

Average Mass

480.5980 Da

Monoisotopic Mass

480.27232 Da

IUPAC Name

(1R,4S,5R,9S,10R,13S)-5,9-dimethyl-14-methylidene-13-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

Traditional Name

(1R,4S,5R,9S,10R,13S)-5,9-dimethyl-14-methylidene-13-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}tetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

C[C@@]12CCC[C@](C)([C@H]1CC[C@@]13CC(=C)[C@@](C1)(CC[C@@H]23)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C26H40O8/c1-14-11-25-9-5-16-23(2,7-4-8-24(16,3)22(31)32)17(25)6-10-26(14,13-25)34-21-20(30)19(29)18(28)15(12-27)33-21/h15-21,27-30H,1,4-13H2,2-3H3,(H,31,32)/t15-,16+,17+,18-,19+,20-,21+,23-,24-,25-,26+/m1/s1

InChI Key

QSIDJGUAAUSPMG-CULFPKEHSA-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
Rubus chingii	LOTUS Database	35616633
Stevia rebaudiana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steviol glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically linked to a steviol (a diterpenoid based on a 13-Hydroxykaur-16-en-18-oic acid) moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Steviol glycosides

Alternative Parents

Substituents

Steviol glycoside
Diterpenoid
Kaurane diterpenoid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Fatty acyl
Monosaccharide
Oxane
Secondary alcohol
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid
Carboxylic acid derivative
Polyol
Organooxygen compound
Primary alcohol
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
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	1.02	ALOGPS
logP	1.88	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	121.3 m³·mol⁻¹	ChemAxon
Polarizability	51.6 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00034697

Chemspider ID

10216322

KEGG Compound ID

Not Available

BioCyc ID

CPD-14502

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21593622

PDB ID

Not Available

ChEBI ID

145029

Good Scents ID

Not Available

References

General References

Richman A, Swanson A, Humphrey T, Chapman R, McGarvey B, Pocs R, Brandle J: Functional genomics uncovers three glucosyltransferases involved in the synthesis of the major sweet glucosides of Stevia rebaudiana. Plant J. 2005 Jan;41(1):56-67. doi: 10.1111/j.1365-313X.2004.02275.x. [PubMed:15610349 ]
Mao Y, Chen Z, Ren Y, Sun Y, Wang Y: Whole-Cell Biocatalyst for Rubusoside Production in Saccharomyces cerevisiae. J Agric Food Chem. 2021 Nov 10;69(44):13155-13163. doi: 10.1021/acs.jafc.1c04873. Epub 2021 Oct 26. [PubMed:34699718 ]
Mohamed AA, Ceunen S, Geuns JM, Van den Ende W, De Ley M: UDP-dependent glycosyltransferases involved in the biosynthesis of steviol glycosides. J Plant Physiol. 2011 Jul 1;168(10):1136-41. doi: 10.1016/j.jplph.2011.01.030. Epub 2011 Apr 7. [PubMed:21477883 ]
Sugimoto N, Sato K, Liu HM, Kikuchi H, Yamazaki T, Maitani T: Analysis of rubusoside and related compounds in tenryocha extract sweetener. Shokuhin Eiseigaku Zasshi. 2002 Aug;43(4):250-3. doi: 10.3358/shokueishi.43.250. [PubMed:12436720 ]

Showing NP-Card for Steviolmonoside (NP0073954)

MOL for NP0073954 (Steviolmonoside)

3D MOL for NP0073954 (Steviolmonoside)

3D SDF for NP0073954 (Steviolmonoside)

3D-SDF for NP0073954 (Steviolmonoside)

PDB for NP0073954 (Steviolmonoside)

3D PDB for NP0073954 (Steviolmonoside)

SMILES for NP0073954 (Steviolmonoside)

INCHI for NP0073954 (Steviolmonoside)

Structure for NP0073954 (Steviolmonoside)

3D Structure for NP0073954 (Steviolmonoside)