Cannabis Compound Database: Showing Compound Card for Steviobioside (CDB005050)

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Record Information

Version

1.0

Created at

2020-04-17 19:04:16 UTC

Updated at

2020-12-07 19:11:29 UTC

CannabisDB ID

CDB005050

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Steviobioside

Description

Steviolbioside 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. Steviolbioside is an extremely weak basic (essentially neutral) compound (based on its pKa). Steviobioside is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-Steviolbioside	ChEBI
Steviolbioside	HMDB
(4alpha)-13-[(2-O-beta-D-Glucopyranosyl-beta-D-glucopyranosyl)oxy]kaur-16-en-18-Oic acid	HMDB
(4Α)-13-[(2-O-β-D-glucopyranosyl-β-D-glucopyranosyl)oxy]kaur-16-en-18-Oic acid	HMDB
Steviol-1,2-bioside	HMDB
Steviobioside	HMDB

Chemical Formula

C₃₂H₅₀O₁₃

Average Molecular Weight

642.74

Monoisotopic Molecular Weight

642.3251

IUPAC Name

(1R,4S,5R,9S,10R,13S)-13-{[(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}-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0^{1,10}.0^{4,9}]hexadecane-5-carboxylic acid

Traditional Name

CAS Registry Number

41093-60-1

SMILES

[H][C@@]1(O[C@@H]2[C@@H](O)[C@H](O)[C@@H](CO)O[C@@]2([H])O[C@@]23C[C@]4(CC2=C)CC[C@]2([H])[C@@](C)(CCC[C@@]2(C)[C@]4([H])CC3)C(O)=O)O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C32H50O13/c1-15-11-31-9-5-18-29(2,7-4-8-30(18,3)28(40)41)19(31)6-10-32(15,14-31)45-27-25(23(38)21(36)17(13-34)43-27)44-26-24(39)22(37)20(35)16(12-33)42-26/h16-27,33-39H,1,4-14H2,2-3H3,(H,40,41)/t16-,17-,18+,19+,20-,21-,22+,23+,24-,25-,26+,27+,29-,30-,31-,32+/m1/s1

InChI Key

OMHUCGDTACNQEX-OSHKXICASA-N

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
Disaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Fatty acyl
Secondary alcohol
Organoheterocyclic compound
Polyol
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Acetal
Primary alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Carbonyl group
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Subcellular:

Source:

Biological:

Animal

Role

Industrial application:

Biological role:

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	-0.05	ALOGPS
logP	0.11	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	215.83 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	153.72 m³·mol⁻¹	ChemAxon
Polarizability	65.8 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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Steviobioside, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Steviobioside, TMS_2_17, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0000009000-cc9722ff2c7fc933c2c9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0000309000-e8fb433a3e5207f6f06e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-016r-0009500000-703e43ff23a745dce7c9	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0i30-0229815000-97d3c9ee0bc95013f21a	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0i00-0139400000-dce4a142bb9331e55e10	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0300-2759410000-468047d7768343b9ff6a	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-02bg-2648749000-b6de1f4d57a5eb333b59	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0329-2957502000-0477cc88d14ee415f65d	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01b9-6759000000-275e525b77d03dbf31b7	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000129000-260dbb0c980f489a7c65	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-11ou-6012392000-a628ef40c3fde7046e8c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0avu-9023740000-6a03289f85fe92ffbc5a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6u-0093436000-c0c038a3c317b2d32437	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfr-0497502000-0afae526329775c5d638	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-9301010000-ca551910d1d0313f1df8	2021-09-22	View Spectrum