Cannabis Compound Database: Showing Compound Card for Trehalose (CDB004875)

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Record Information

Version

1.0

Created at

2020-04-17 18:45:49 UTC

Updated at

2020-11-18 16:38:54 UTC

CannabisDB ID

CDB004875

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Trehalose

Description

Trehalose, also known as alpha-D-trehalose or (GLC)2, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon. Trehalose is an extremely weak basic (essentially neutral) compound (based on its pKa). Trehalose exists in all living species, ranging from bacteria to humans. trehalose can be converted into β-D-glucose and α-D-glucose; which is mediated by the enzyme trehalase. In humans, trehalose is involved in trehalose degradation. Outside of the human body, Trehalose has been detected, but not quantified in, a few different foods, such as bitter gourds, garden tomato, and mushrooms. This could make trehalose a potential biomarker for the consumption of these foods. Trehalose 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
(GLC)2	ChEBI
alpha,Alpha'-trehalose	ChEBI
alpha-D-GLCP-(11)-alpha-D-GLCP	ChEBI
alpha-D-Glucopyranosyl-alpha-D-glucopyranoside	ChEBI
alpha-D-Trehalose	ChEBI
alpha-Trehalose	ChEBI
D-(+)-Trehalose	ChEBI
Ergot sugar	ChEBI
Mycose	ChEBI
a,Alpha'-trehalose	Generator
Α,alpha'-trehalose	Generator
a-D-GLCP-(11)-a-D-GLCP	Generator
Α-D-GLCP-(11)-α-D-GLCP	Generator
a-D-Glucopyranosyl-a-D-glucopyranoside	Generator
Α-D-glucopyranosyl-α-D-glucopyranoside	Generator
a-D-Trehalose	Generator
Α-D-trehalose	Generator
a-Trehalose	Generator
Α-trehalose	Generator
alpha,alpha-Trehalose	HMDB
D-Trehalose-anhydrous	HMDB
delta-Trehalose-anhydrous	HMDB
D-Trehalose	HMDB
Natural trehalose	HMDB
O-D-Glucopyranosyl-(1→1)-D-glucopyranoside	HMDB
alpha,Alpha'-D-trehalose	HMDB
alpha-D-Glucopyranosyl alpha-D-glucopyranoside	HMDB
Α,α'-D-trehalose	HMDB
Α,α-trehalose	HMDB
Α,α’-D-trehalose	HMDB
Α-D-glucopyranosyl α-D-glucopyranoside	HMDB
Trehalose	HMDB

Chemical Formula

C₁₂H₂₂O₁₁

Average Molecular Weight

342.3

Monoisotopic Molecular Weight

342.1162

IUPAC Name

(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-3,4,5-triol

Traditional Name

α,α'-trehalose

CAS Registry Number

99-20-7

SMILES

OC[C@H]1O[C@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C12H22O11/c13-1-3-5(15)7(17)9(19)11(21-3)23-12-10(20)8(18)6(16)4(2-14)22-12/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11-,12-/m1/s1

InChI Key

HDTRYLNUVZCQOY-LIZSDCNHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Disaccharide
Oxane
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

trehalose (CHEBI:16551 )
Disaccharides (C01083 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Microbe:

Propionibacterium

Burkholderia:

Burkholderia stabilis

Escherichia:

Escherichia coli

Plant:

Cucurbitaceae

Biological location:

Organ and components:

Kidney

Tissue and substructures:

Biofluid and excreta:

Cell and elements:

Extracellular

Element:

Platelet

Cell:

Fibroblast

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	203 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	68.9 g / 100 g at 20 °C	Wikipedia
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3	ALOGPS
logP	-4.7	ChemAxon
logS	0.24	ALOGPS
pKa (Strongest Acidic)	11.91	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	189.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.34 m³·mol⁻¹	ChemAxon
Polarizability	31.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-022c-9100000000-33d1067ccb0cb2dda51d	2018-05-25	View Spectrum
GC-MS	Trehalose, 8 TMS, GC-MS Spectrum	splash10-0j4m-0932000000-8d7c80edd7f55e92ea29	Spectrum
GC-MS	Trehalose, 8 TMS, GC-MS Spectrum	splash10-00di-9511000000-b710c7c4bd86fd5f1af0	Spectrum
GC-MS	Trehalose, 8 TMS, GC-MS Spectrum	splash10-00di-9511000000-2e5f22e6ba282283a569	Spectrum
GC-MS	Trehalose, 8 TMS, GC-MS Spectrum	splash10-00di-9832000000-b3259de2e25ea7293565	Spectrum
GC-MS	Trehalose, 8 TMS, GC-MS Spectrum	splash10-0wos-0921000000-68fb82f427417ec703a0	Spectrum
GC-MS	Trehalose, 8 TMS, GC-MS Spectrum	splash10-0j4m-0943000000-07c11d483e4278dc639a	Spectrum
GC-MS	Trehalose, 8 TMS, GC-MS Spectrum	splash10-0wmm-0953000000-b74403fa3ce6ce0339eb	Spectrum
GC-MS	Trehalose, non-derivatized, GC-MS Spectrum	splash10-0i04-0932000000-8de0421184ae3291ea53	Spectrum
GC-MS	Trehalose, 8 TMS, GC-MS Spectrum	splash10-00di-8932000000-c327fe31b8d3e86dd97d	Spectrum
GC-MS	Trehalose, 8 TMS, GC-MS Spectrum	splash10-0j4l-0954000000-33e230d28780be607983	Spectrum
GC-MS	Trehalose, non-derivatized, GC-MS Spectrum	splash10-0j4m-0932000000-8d7c80edd7f55e92ea29	Spectrum
GC-MS	Trehalose, non-derivatized, GC-MS Spectrum	splash10-00di-9511000000-b710c7c4bd86fd5f1af0	Spectrum
GC-MS	Trehalose, non-derivatized, GC-MS Spectrum	splash10-00di-9511000000-2e5f22e6ba282283a569	Spectrum
GC-MS	Trehalose, non-derivatized, GC-MS Spectrum	splash10-00di-9832000000-b3259de2e25ea7293565	Spectrum
GC-MS	Trehalose, non-derivatized, GC-MS Spectrum	splash10-0wos-0921000000-68fb82f427417ec703a0	Spectrum
GC-MS	Trehalose, non-derivatized, GC-MS Spectrum	splash10-0j4m-0943000000-07c11d483e4278dc639a	Spectrum
GC-MS	Trehalose, non-derivatized, GC-MS Spectrum	splash10-0wmm-0953000000-b74403fa3ce6ce0339eb	Spectrum
GC-MS	Trehalose, non-derivatized, GC-MS Spectrum	splash10-0i04-0932000000-8de0421184ae3291ea53	Spectrum
GC-MS	Trehalose, non-derivatized, GC-MS Spectrum	splash10-00di-8932000000-c327fe31b8d3e86dd97d	Spectrum
GC-MS	Trehalose, non-derivatized, GC-MS Spectrum	splash10-0j4l-0954000000-33e230d28780be607983	Spectrum
GC-MS	Trehalose, non-derivatized, GC-MS Spectrum	splash10-0i2d-0921000000-9e633378baf1645df2a1	Spectrum
Predicted GC-MS	Trehalose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-08ni-9554000000-e418bec346785e269084	Spectrum
Predicted GC-MS	Trehalose, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-2553419000-dd0bea0ade3ee46308dc	Spectrum
Predicted GC-MS	Trehalose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Trehalose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-1901000000-865e9e390fac7d13c2f8	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9500000000-7d4c9de285c2872d2320	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-c71f25d08b875caff6b6	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0006-0019000000-3b4e276ff5686c841bdd	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0fdx-8905000000-fafde7828ce0d63fe618	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0fdx-8905000000-f4b4b3ad528ea3bf43c2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-004i-0900000000-d382926500274fb84a46	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0udi-0090000000-10524d7a715f8a0ed265	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0006-0019000000-3b4e276ff5686c841bdd	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-9ae5587f61124e19e967	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-052r-9400000000-912468a68a25ec147569	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0926000000-b1b3f8b4fbacdcc1180f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0ab9-9200000000-0088f187ae8b6d9b5c2e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-9200000000-8437afa67780c28771b8	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-5809000000-5a5cec80f792fdde61bb	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-0900000000-c4415a0eb58b8c1c5640	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01t9-0926000000-af9f579519c642acb94f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9300000000-197e82f358194cd04b3c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-3593000000-97d3b3b35a65f632fddd	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03ec-0903000000-8981579ae1dd58ba65c9	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1901000000-4c8ec381daa00b88a539	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-5900000000-89485b49a32afa256bdc	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-4918000000-df3152da1740bcb45d3d	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03mi-3901000000-c9e67703b1ef9ca4f8cc	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002f-9600000000-b9d2971c377f79dd6238	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Trehalose Degradation		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Trehalase	TREH	11q23.3	O43280	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000975

DrugBank ID

DB12310

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16551

References

General References

Not Available

Enzymes

Enzyme Details

1. Trehalase

General function:: Involved in catalytic activity
Specific function:: Intestinal trehalase is probably involved in the hydrolysis of ingested trehalose.
Gene Name:: TREH
Uniprot ID:: O43280
Molecular weight:: 66567.26

Showing Compound Card for Trehalose (CDB004875)

Structure for CDB004875 (Trehalose)

Enzymes