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Showing NP-Card for Trehalose (NP0000014)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2020-09-11 01:14:33 UTC
NP-MRD IDNP0000014
Secondary Accession NumbersNone
Natural Product Identification
Common NameTrehalose
DescriptionTrehalose, 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.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(GLC)2ChEBI
alpha,Alpha'-trehaloseChEBI
alpha-D-GLCP-(11)-alpha-D-GLCPChEBI
alpha-D-Glucopyranosyl-alpha-D-glucopyranosideChEBI
alpha-D-TrehaloseChEBI
alpha-TrehaloseChEBI
D-(+)-TrehaloseChEBI
Ergot sugarChEBI
MycoseChEBI
a,Alpha'-trehaloseGenerator
Α,alpha'-trehaloseGenerator
a-D-GLCP-(11)-a-D-GLCPGenerator
Α-D-GLCP-(11)-α-D-GLCPGenerator
a-D-Glucopyranosyl-a-D-glucopyranosideGenerator
Α-D-glucopyranosyl-α-D-glucopyranosideGenerator
a-D-TrehaloseGenerator
Α-D-trehaloseGenerator
a-TrehaloseGenerator
Α-trehaloseGenerator
alpha,alpha-TrehaloseHMDB
D-Trehalose-anhydrousHMDB
delta-Trehalose-anhydrousHMDB
D-TrehaloseHMDB
Natural trehaloseHMDB
O-D-Glucopyranosyl-(1→1)-D-glucopyranosideHMDB
alpha,Alpha'-D-trehaloseHMDB
alpha-D-Glucopyranosyl alpha-D-glucopyranosideHMDB
Α,α'-D-trehaloseHMDB
Α,α-trehaloseHMDB
Α,α’-D-trehaloseHMDB
Α-D-glucopyranosyl α-D-glucopyranosideHMDB
TrehaloseHMDB
Chemical FormulaC12H22O11
Average Molecular Weight342.2965
Monoisotopic Molecular Weight342.116211546
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 Nameα,α'-trehalose
CAS Registry Number99-20-7
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 KeyHDTRYLNUVZCQOY-LIZSDCNHSA-N
Spectra
Spectrum TypeDescriptionView
1D NMR13C NMR SpectrumJSpectraViewer
1D NMR1H NMR SpectrumJSpectraViewer
1D NMR1H NMR SpectrumJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumJSpectraViewer
Species of Origin
SpeciesAnimalia; Eubacteria; Fungi
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point203 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility592 g/LALOGPS
logP-3ALOGPS
logP-4.7ChemAxon
logS0.24ALOGPS
pKa (Strongest Acidic)11.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.34 m³·mol⁻¹ChemAxon
Polarizability31.14 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
User Submitted Data
Not Available
HMDB IDHMDB0000975
DrugBank IDDB12310
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001114
KNApSAcK IDC00001152
Chemspider ID7149
KEGG Compound IDC01083
BioCyc IDTREHALOSE
BiGG ID36774
Wikipedia LinkTrehalose
METLIN ID5913
PubChem Compound7427
PDB IDNot Available
ChEBI ID16551
References
General References
  1. Potier M, Dallaire L, Melancon SB: Occurrence and properties of fetal intestinal glycosidases (disaccharidases) in human amniotic fluid. Biol Neonate. 1975;27(3-4):141-52. [PubMed:241430 ]
  2. Citron DM, Baron EJ, Finegold SM, Goldstein EJ: Short prereduced anaerobically sterilized (PRAS) biochemical scheme for identification of clinical isolates of bile-resistant Bacteroides species. J Clin Microbiol. 1990 Oct;28(10):2220-3. [PubMed:2229345 ]
  3. Yoshioka S, Aso Y: A quantitative assessment of the significance of molecular mobility as a determinant for the stability of lyophilized insulin formulations. Pharm Res. 2005 Aug;22(8):1358-64. Epub 2005 Aug 3. [PubMed:16078146 ]
  4. Guo N, Puhlev I, Brown DR, Mansbridge J, Levine F: Trehalose expression confers desiccation tolerance on human cells. Nat Biotechnol. 2000 Feb;18(2):168-71. [PubMed:10657122 ]
  5. Nie Y, de Pablo JJ, Palecek SP: Platelet cryopreservation using a trehalose and phosphate formulation. Biotechnol Bioeng. 2005 Oct 5;92(1):79-90. [PubMed:15937943 ]
  6. Fujita Y, Naka T, Doi T, Yano I: Direct molecular mass determination of trehalose monomycolate from 11 species of mycobacteria by MALDI-TOF mass spectrometry. Microbiology. 2005 May;151(Pt 5):1443-52. [PubMed:15870454 ]
  7. Lu FQ, Liu JH, Ouyang XL, Li XJ, Zhou J, Zhuang Y: [Process of human platelets loaded with rehalose before lyophilization]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2006 Feb;14(1):156-61. [PubMed:16584614 ]
  8. Shirkhanzadeh M: Microneedles coated with porous calcium phosphate ceramics: effective vehicles for transdermal delivery of solid trehalose. J Mater Sci Mater Med. 2005 Jan;16(1):37-45. [PubMed:15754142 ]
  9. Eroglu A, Russo MJ, Bieganski R, Fowler A, Cheley S, Bayley H, Toner M: Intracellular trehalose improves the survival of cryopreserved mammalian cells. Nat Biotechnol. 2000 Feb;18(2):163-7. [PubMed:10657121 ]
  10. Arguelles JC, Rodriguez T, Alvarez-Peral FJ: Trehalose hydrolysis is not required for human serum-induced dimorphic transition in Candida albicans: evidence from a tps1/tps1 mutant deficient in trehalose synthesis. Res Microbiol. 1999 Oct;150(8):521-9. [PubMed:10577485 ]
  11. Corning BF, Murphy JC, Fox JG: Group G streptococcal lymphadenitis in rats. J Clin Microbiol. 1991 Dec;29(12):2720-3. [PubMed:1757539 ]
  12. Davies JE, Sarkar S, Rubinsztein DC: Trehalose reduces aggregate formation and delays pathology in a transgenic mouse model of oculopharyngeal muscular dystrophy. Hum Mol Genet. 2006 Jan 1;15(1):23-31. Epub 2005 Nov 25. [PubMed:16311254 ]
  13. Ma X, Jamil K, Macrae TH, Clegg JS, Russell JM, Villeneuve TS, Euloth M, Sun Y, Crowe JH, Tablin F, Oliver AE: A small stress protein acts synergistically with trehalose to confer desiccation tolerance on mammalian cells. Cryobiology. 2005 Aug;51(1):15-28. [PubMed:15963489 ]
  14. Alcoba-Florez J, Mendez-Alvarez S, Cano J, Guarro J, Perez-Roth E, del Pilar Arevalo M: Phenotypic and molecular characterization of Candida nivariensis sp. nov., a possible new opportunistic fungus. J Clin Microbiol. 2005 Aug;43(8):4107-11. [PubMed:16081957 ]
  15. Chang L, Shepherd D, Sun J, Ouellette D, Grant KL, Tang XC, Pikal MJ: Mechanism of protein stabilization by sugars during freeze-drying and storage: native structure preservation, specific interaction, and/or immobilization in a glassy matrix? J Pharm Sci. 2005 Jul;94(7):1427-44. [PubMed:15920775 ]
  16. Sasnoor LM, Kale VP, Limaye LS: A combination of catalase and trehalose as additives to conventional freezing medium results in improved cryoprotection of human hematopoietic cells with reference to in vitro migration and adhesion properties. Transfusion. 2005 Apr;45(4):622-33. [PubMed:15819685 ]
  17. Alvarez-Peral FJ, Arguelles JC: Changes in external trehalase activity during human serum-induced dimorphic transition in Candida albicans. Res Microbiol. 2000 Dec;151(10):837-43. [PubMed:11191809 ]
  18. Berlutti F, Thaller MC, Dainelli B, Pezzi R: T-mod pathway, a reduced sequence for identification of gram-negative urinary tract pathogens. J Clin Microbiol. 1989 Jul;27(7):1646-9. [PubMed:2768451 ]