创建日期
2005-11-16 15:48:42 UTC
更新日期
2021-09-14 15:44:44 UTC
描述
Melibiose (CAS: 585-99-9) is a disaccharide consisting of one galactose and one glucose moiety in an alpha (1-6) glycosidic linkage. This sugar is produced and metabolized only by enteric and lactic acid bacteria and other microbes, such as Dickeya dadantii, Escherichia, Leuconostoc, and Saccharomyces (PMID: 19734309, 28453942). It is not an endogenous metabolite but may be obtained from the consumption of partially fermented molasses, brown sugar, or honey. Antibodies to melibiose will appear in individuals affected by Chagas' disease (Trypanosoma cruzi infection). Melibiose is not metabolized by humans but can be broken down by gut microflora, such as E. coli. In fact, E. coli is able to utilize melibiose as a sole source of carbon. Melibiose is first imported by the melibiose permease, MelB and then converted into β-D-glucose and β-D-galactose by the α-galactosidase encoded by melA. Because of its poor digestibility, melibiose (along with rhamnose) can be used together for noninvasive intestinal mucosa barrier testing. This test can be used to assess malabsorption or impairment of intestinal permeability. Recent studies with dietary melibiose have shown that it can strongly affect the Th cell responses to an ingested antigen. It has been suggested that melibiose could be used to enhance the induction of oral tolerance (PMID: 17986780).
同义词
1:6-O-alpha-D-Galactopyranosyl-D-glucose
2:6-O-alpha-D-Galactopyranosyl-alpha-D-glucopyranose
3:6-O-Α-D-galactopyranosyl-D-glucose
4:6-O-Α-D-galactopyranosyl-α-D-glucopyranose
5:D-(+)-Melibiose
6:D-Melibiose
7:alpha-D-Melibiose
8:alpha-Melibiose
9:Α-D-melibiose
10:Α-melibiose
11:Melibiose
化学名称
(2S,3R,4S,5S,6R)-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol
传统名称
(2S,3R,4S,5S,6R)-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol
代谢物结构字符串
OC[C@H]1O[C@H](OC[C@H]2O[C@H](O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O
inchi标识符
InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5+,6-,7+,8+,9-,10-,11+,12+/m1/s1
印记键
DLRVVLDZNNYCBX-CQHUIXDMSA-N
分类学
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.
description:O-glycosyl compounds
kingdom:Organic compounds
super_class:Organic oxygen compounds
class:Organooxygen compounds
sub_class:Carbohydrates and carbohydrate conjugates
molecular_framework:Aliphatic heteromonocyclic compounds
1:Acetals
2:Disaccharides
3:Hemiacetals
4:Hydrocarbon derivatives
5:Oxacyclic compounds
6:Oxanes
7:Polyols
8:Primary alcohols
9:Secondary alcohols
10:Acetal
11:Alcohol
12:Aliphatic heteromonocyclic compound
13:Disaccharide
14:Hemiacetal
15:Hydrocarbon derivative
16:O-glycosyl compound
17:Organoheterocyclic compound
18:Oxacycle
19:Oxane
20:Polyol
21:Primary alcohol
22:Secondary alcohol
本体论
term:Disposition
definition:A concept that describes the origin of a chemical, its location within an organism, or its route of exposure.
parent_id:
level:1
type:parent
term:Route of exposure
definition:A mean by which a chemical agent comes in contact with an organism, either under intended or unintended circumstances.
parent_id:7724
*level:2
type:parent
term:Enteral
definition:Chemical exposure via the alimentary canal (mouth to anus).
parent_id:7743
**level:3
type:parent
term:Ingestion
definition:Chemical exposure facilitated by entry through the mouth.
parent_id:7744
***level:4
type:child
synonym:Digestion
term:Source
definition:Natural or synthetic origin of a chemical.
parent_id:7724
*level:2
type:parent
term:Food
definition:
parent_id:7735
**level:3
type:child
term:Biological
definition:A living organism (species or a higher taxonomy rank), in which a chemical can be found.
parent_id:7735
**level:3
type:parent
term:Animal
definition:A living organism belonging to the kingdom animalia. it feeds on organic matter, typically having specialized sense organs and nervous system and able to respond rapidly to stimuli.
parent_id:7736
***level:4
type:child
synonym:Fauna
term:Saccharomyces cerevisiae
definition:
parent_id:7736
***level:4
type:child
synonym:Baker's yeast
term:Microbe
definition:A living organism that is of a microscopic scale, either single-celled or a cluster of cells.
parent_id:7736
***level:4
type:parent
term:Plant
definition:A living organism belonging to the kingdom plantea. typically, it grows in a permanent site, absorbs water and inorganic substances through its roots, and synthesizes nutrients in its leaves by photosynthesis using the green pigment chlorophyll. examples incude trees, shrubs, herbs, grasses, ferns, and mosses.
parent_id:7736
***level:4
type:parent
synonym:Flora
term:Biological location
definition:The physiological origin within an organism, including anatomical compnents, biofluids and excreta.
parent_id:7724
*level:2
type:parent
term:Organ and components
definition:An anatomical organizational level including multiple tissues or substructures, which enables a common biological function.
parent_id:7725
**level:3
type:parent
term:Spleen
definition:An abdominal organ that is part of the hematopoietic and immune systems. it is composed of the white pulp and the red pulp and is surrounded by a capsule. (nci).
parent_id:7727
***level:4
type:child
term:Biofluid and excreta
definition:A liquid, semi-solid or solid material originating in the body.
parent_id:7725
**level:3
type:parent
term:Urine
definition:Excretion in liquid state processed by the kidney.
parent_id:7731
***level:4
type:child
term:Cell and elements
definition:An anatomical organizational level comprising of a single cell (or a fragment in some exceptions). a cell is defined by its type or function. it is the smallest unit of living structure capable of independent existence, composed of a membrane-enclosed mass of protoplasm and containing a nucleus or nucleoid.
parent_id:7725
**level:3
type:parent
term:Extracellular
definition:The space external to the outermost structure of a cell.
parent_id:7732
***level:4
type:child
synonym:Extracellular region
term:Process
definition:Biological or chemical events, or a series thereof, leading to a known function or end-product.
parent_id:
level:1
type:parent
term:Naturally occurring process
definition:Naturally-occurring molecular events or a series thereof, leading to a known function or end-product.
parent_id:7659
*level:2
type:parent
term:Biological process
definition:Biological or chemical events or a series thereof, leading to a known function or end-product within an organism.
parent_id:7660
**level:3
type:parent
term:Biochemical pathway
definition:A linked series of chemical reactions that occur in a defined order within or between organism cells, and lead to a known function or end product.
parent_id:7661
***level:4
type:parent
实验性质
1:
kind:water_solubility
value:1000.0 mg/mL
source:
2:
kind:melting_point
value:84 °C
source:
预测性质
1:
kind:logp
value:-3.00
source:ALOGPS
2:
kind:logs
value:0.17
source:ALOGPS
3:
kind:solubility
value:511 g/L
source:ALOGPS
4:
kind:logp
value:-4.7
source:ChemAxon
5:
kind:pka_strongest_acidic
value:11.25
source:ChemAxon
6:
kind:pka_strongest_basic
value:-3
source:ChemAxon
7:
kind:iupac
value:(2S,3R,4S,5S,6R)-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol
source:ChemAxon
8:
kind:average_mass
value:342.2965
source:ChemAxon
9:
kind:mono_mass
value:342.116211546
source:ChemAxon
10:
kind:smiles
value:OC[C@H]1O[C@H](OC[C@H]2O[C@H](O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@H]1O
source:ChemAxon
11:
kind:formula
value:C12H22O11
source:ChemAxon
12:
kind:inchi
value:InChI=1S/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5+,6-,7+,8+,9-,10-,11+,12+/m1/s1
source:ChemAxon
13:
kind:inchikey
value:DLRVVLDZNNYCBX-CQHUIXDMSA-N
source:ChemAxon
14:
kind:polar_surface_area
value:189.53
source:ChemAxon
15:
kind:refractivity
value:68.34
source:ChemAxon
16:
kind:polarizability
value:31.19
source:ChemAxon
17:
kind:rotatable_bond_count
value:4
source:ChemAxon
18:
kind:acceptor_count
value:11
source:ChemAxon
19:
kind:donor_count
value:8
source:ChemAxon
20:
kind:physiological_charge
value:0
source:ChemAxon
21:
kind:formal_charge
value:0
source:ChemAxon
22:
kind:number_of_rings
value:2
source:ChemAxon
23:
kind:bioavailability
value:No
source:ChemAxon
24:
kind:rule_of_five
value:No
source:ChemAxon
25:
kind:ghose_filter
value:No
source:ChemAxon
26:
kind:veber_rule
value:No
source:ChemAxon
27:
kind:mddr_like_rule
value:No
source:ChemAxon
1:
type:Specdb::NmrTwoD
spectrum_id:2048
2:
type:Specdb::MsMs
spectrum_id:2322607
3:
type:Specdb::MsMs
spectrum_id:2322608
4:
type:Specdb::MsMs
spectrum_id:2322609
5:
type:Specdb::MsMs
spectrum_id:2615949
6:
type:Specdb::MsMs
spectrum_id:2615950
7:
type:Specdb::MsMs
spectrum_id:2615951
8:
type:Specdb::CMs
spectrum_id:155833
生物学性质
1:
cellular:(1):Extracellular
2:
biospecimen:(1):Urine
3:
tissue:(1):Spleen
4:
[1]:
name:Galactose Metabolism
smpdb_id:SMP00043
kegg_map_id:map00052
[2]:
name:Galactosemia
smpdb_id:SMP00182
kegg_map_id:
正常浓度
1:
biospecimen:Urine
concentration_value:< 0.1
concentration_units:umol/mmol creatinine
subject_age:Children (1-13 years old)
subject_sex:Both
subject_condition:Normal
异常浓度
1:
biospecimen:Urine
concentration_value:
concentration_units:
patient_age:Adult (>18 years old)
patient_sex:Both
patient_information:Bladder cancer
综合参考
Pictet, Ame; Vogel, Hans. The synthesis of melibiose. Helvetica Chimica Acta (1927), 10 280.
一般参考
1:
protein_accession:HMDBP00723
name:Alpha-galactosidase A
uniprot_id:P06280
gene_name:GLA
protein_type:Enzyme
2:
protein_accession:HMDBP03069
name:Maltase-glucoamylase, intestinal
uniprot_id:O43451
gene_name:MGAM
protein_type:Enzyme
3:
protein_accession:HMDBP05979
name:Neutral alpha-glucosidase C
uniprot_id:Q8TET4
gene_name:GANC
protein_type:Enzyme
蛋白质结合
1:
reference_text:Almeida IC, Milani SR, Gorin PA, Travassos LR: Complement-mediated lysis of Trypanosoma cruzi trypomastigotes by human anti-alpha-galactosyl antibodies. J Immunol. 1991 Apr 1;146(7):2394-400.
pubmed_id:1706399
2:
reference_text:Sharma A, Ahmed H, Allen HJ: Isolation of a melibiose-binding protein from human spleen. Glycoconj J. 1995 Feb;12(1):17-21.
pubmed_id:7795409
3:
reference_text:Steuer MK, Steuer M, Bonkowsky V, Gabius HJ, Hofstadter F: Characterization of sugar receptor expression by neoglycoproteins in oral and oropharyngeal squamous cell carcinomas. Eur Arch Otorhinolaryngol. 1995;252(5):292-7.
pubmed_id:7576587
4:
reference_text:Vaughan HA, Loveland BE, Sandrin MS: Gal alpha(1,3)Gal is the major xenoepitope expressed on pig endothelial cells recognized by naturally occurring cytotoxic human antibodies. Transplantation. 1994 Oct 27;58(8):879-82.
pubmed_id:7524207
5:
reference_text:Barboza Junior MS, Silva TM, Guerrant RL, Lima AA: Measurement of intestinal permeability using mannitol and lactulose in children with diarrheal diseases. Braz J Med Biol Res. 1999 Dec;32(12):1499-504.
pubmed_id:10585631
6:
reference_text:Furukawa K, Ying R, Nakajima T, Matsuki T: Hemagglutinins in fungus extracts and their blood group specificity. Exp Clin Immunogenet. 1995;12(4):223-31.
pubmed_id:8919354
7:
reference_text:Gibbons RJ, Qureshi JV: Inhibition of adsorption of Streptococcus mutans strains to saliva-treated hydroxyapatite by galactose and certain amines. Infect Immun. 1979 Dec;26(3):1214-7.
pubmed_id:528053
8:
reference_text:Nicolopoulou A, Zoumbou K, Papageorgacopoulou N, Papapetropoulou M: Metabolic and compositional changes in Escherichia coli cells starved in seawater. Microbiol Res. 1994 Nov;149(4):343-50.
pubmed_id:7842233
9:
reference_text:Wu AM, Song SC, Chen YY, Gilboa-Garber N: Defining the carbohydrate specificities of aplysia gonad lectin exhibiting a peculiar D-galacturonic acid affinity. J Biol Chem. 2000 May 12;275(19):14017-24.
pubmed_id:10799474
10:
reference_text:Rietra PJ, Van den Bergh FA, Tager JM: Properties of the residual alpha-galactosidase activity in the tissues of a Fabry hemizygote. Clin Chim Acta. 1975 Aug 4;62(3):401-13.
pubmed_id:809216
11:
reference_text:Colby SM, Harrington DJ, Russell RR: Identification and genetic characterisation of melibiose-negative isolates of Streptococcus mutans. Caries Res. 1995;29(5):407-12.
pubmed_id:8521444
12:
reference_text:Tomita K, Nagura T, Okuhara Y, Nakajima-Adachi H, Shigematsu N, Aritsuka T, Kaminogawa S, Hachimura S: Dietary melibiose regulates th cell response and enhances the induction of oral tolerance. Biosci Biotechnol Biochem. 2007 Nov;71(11):2774-80. Epub 2007 Nov 7.
pubmed_id:17986780
13:
reference_text:Hugouvieux-Cotte-Pattat N, Charaoui-Boukerzaza S: Catabolism of raffinose, sucrose, and melibiose in Erwinia chrysanthemi 3937. J Bacteriol. 2009 Nov;191(22):6960-7. doi: 10.1128/JB.00594-09. Epub 2009 Sep 4.
pubmed_id:19734309
14:
reference_text:Xu W, Yu S, Liu Q, Zhang T, Jiang B, Mu W: Enzymatic Production of Melibiose from Raffinose by the Levansucrase from Leuconostoc mesenteroides B-512 FMC. J Agric Food Chem. 2017 May 17;65(19):3910-3918. doi: 10.1021/acs.jafc.7b01265. Epub 2017 May 5.
pubmed_id:28453942