ChemFOnt: Showing chemical card for Trehalose (CFc000000776)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:16 UTC

Chemfont ID

CFc000000776

Molecule Identification

Common Name

Trehalose

Definition

Trehalose, also known as mycose, is a 1-alpha (disaccharide) sugar found extensively but not abundantly in nature. It is thought to be implicated in anhydrobiosis - the ability of plants and animals to withstand prolonged periods of desiccation. The sugar is thought to form a gel phase as cells dehydrate, which prevents disruption of internal cell organelles by effectively splinting them in position. Rehydration then allows normal cellular activity to be resumed without the major, generally lethal damage that would normally follow a dehydration/reyhdration cycle. Trehalose is a non-reducing sugar formed from two glucose units joined by a 1-1 alpha bond giving it the name of alpha-D-glucopyranoglucopyranosyl-1,1-alpha-D-glucopyranoside. The bonding makes trehalose very resistant to acid hydrolysis, and therefore stable in solution at high temperatures even under acidic conditions. The bonding also keeps non-reducing sugars in closed-ring form, such that the aldehyde or ketone end-groups do not bind to the lysine or arginine residues of proteins (a process called glycation). The enzyme trehalase, present but not abundant in most people, breaks it into two glucose molecules, which can then be readily absorbed in the gut. Trehalose is an important components of insects circulating fluid. It acts as a storage form of insect circulating fluid and it is important in respiration. Trehalose has also been found to be a metabolite of Burkholderia, Escherichia and Propionibacterium (PMID:12105274 ; PMID:25479689 ) (krishikosh.egranth.ac.in/bitstream/1/84382/1/88571%20P-1257.pdf).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
a-D-Glucopyranosyl b-D-glucopyranoside	HMDB
b-D-Glucopyranosyl a-D-glucopyranoside, 9ci, 8ci	HMDB

Chemical Formula

C₁₂H₂₂O₁₁

Average Molecular Weight

342.2965

Monoisotopic Molecular Weight

342.116211546

IUPAC Name

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

Traditional Name

trehalose

CAS Registry Number

99-20-7

SMILES

OCC1OC(OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O

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

InChI Key

HDTRYLNUVZCQOY-UHFFFAOYSA-N

Chemical Taxonomy

Description

This compound 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

a disaccharide (TREHALOSE )

Functional Ontology

Not Available

Epidermis (HMDB: HMDB0000975)

Muscle tissue

Skeletal muscle (HMDB: HMDB0000975)

Cell

Fibroblasts (HMDB: HMDB0000975)

Hematocyte

Platelet (HMDB: HMDB0000975)

Organ

Kidney (HMDB: HMDB0000975)

Excreta

Biofluid or Excreta

Feces (PMID: 22944170)
Urine (HMDB: HMDB0000975)

Cellular substructure

Extracellular (HMDB: HMDB0000975)

Source

Exogenous

Exogenous (HMDB: HMDB0000975)

Food

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)
Grape wine (FooDB: FOOD00612)

Vegetable

Mushroom

Fruit vegetable

Garden tomato (FooDB: FOOD00171)

Gourd

Bitter gourd (FooDB: FOOD00115)

Endogenous

Endogenous (HMDB: HMDB0000975)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Trehalose Degradation (PathBank: SMP0063682)
Starch and Sucrose Metabolism (PathBank: SMP0000958)
Starch and Sucrose Metabolism (PathBank: SMP0002380)
Secondary Metabolites: Trehalose Biosynthesis and Metabolism (PathBank: SMP0121327)
Trehalose Biosynthesis I (PathBank: SMP0122252)
Trehalose Degradation I (Low Osmolarity) (PathBank: SMP0122258)
Chitin Biosynthesis (PathBank: SMP0094667)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	592 g/L	ALOGPS
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	31.6 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

External Links

HMDB ID

HMDB29880

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001115

KNApSAcK ID

Not Available

Chemspider ID

1111

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1143

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Murao, Sawao; Nagano, Hiroto; Ogura, Sei; Nishino, Toyokazu. Enzymic synthesis of trehalose from maltose. Agricultural and Biological Chemistry (1985), 49(7), 2113-18.

Showing chemical card for Trehalose (CFc000000776)

MOL for CFc000000776 (Trehalose)

3D MOL for CFc000000776 (Trehalose)

3D SDF for CFc000000776 (Trehalose)

3D-SDF for CFc000000776 (Trehalose)

PDB for CFc000000776 (Trehalose)

3D PDB for CFc000000776 (Trehalose)

SMILES for CFc000000776 (Trehalose)

INCHI for CFc000000776 (Trehalose)

Structure for CFc000000776 (Trehalose)

3D Structure for CFc000000776 (Trehalose)