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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H22O11
Molecular Weight 342.2965
Optical Activity UNSPECIFIED
Defined Stereocenters 10 / 10
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GENTIOBIOSE, .BETA.-

SMILES

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

InChIKey=DLRVVLDZNNYCBX-LIZSDCNHSA-N
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

HIDE SMILES / InChI

Molecular Formula C12H22O11
Molecular Weight 342.2965
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

beta-Gentiobiose is a naturally occurring disaccharide. It was proved to be potent inhibitors of the lytic activity of NK cells as well as of cytotoxic T lymphocytes activated in mixed lymphocyte cultures.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Adjuvant potential of archaeal synthetic glycolipid mimetics critically depends on the glyco head group structure.
2008-07
Inhibition of cell-mediated lympholysis by cloned and uncloned lines of natural killer cells and cytotoxic T lymphocytes with sugars and lectins.
1984-10-01
The effect of unphosphorylated and phosphorylated sugar moieties on human and mouse natural killer cell activity: is there selective inhibition at the level of target recognition and lytic acceptor site?
1983-08
Inhibition of spontaneous but not antibody-dependent cell-mediated cytotoxicity by simple sugars: evidence that endogenous lectins may mediate spontaneous cell-mediated cytotoxicity.
1981-09

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Ten to twenty million normal peripheral blood mononuclear cells were incubated with 100 u./ml interferon at 37 Celcius degrees for either 2 or 16 hr. After washing, target cells (colon tumor cell line or K-562 cells) were added and incubated for 18 h, using 75 mM of beta-gentiobiose and 1: 1, 2 5: 1, 5: 1, 7 5: 1, 10: 1, 17 5: 1, 25:1, 37-5: 1 and 50: 1. beta-Gentiobiose inhibited spontaneous cell-mediated cytotoxicity by 50% in Chang cell line cells at a 50: killer to target cell ratio and by 75% in K-562 cells at a 50:1 killer to target cell ratio.
Substance Class Chemical
Created
by admin
on Mon Mar 31 20:33:23 GMT 2025
Edited
by admin
on Mon Mar 31 20:33:23 GMT 2025
Record UNII
N2VA1H3TIQ
Record Status Validated (UNII)
Record Version
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Name Type Language
.BETA.-D-GLUCOSE, 6-O-.BETA.-D-GLUCOPYRANOSYL-
Preferred Name English
GENTIOBIOSE, .BETA.-
Common Name English
GENTIOBIOSE .BETA.-FORM [MI]
Common Name English
6-O-.BETA.-D-GLUCOPYRANOSYL-.BETA.-D-GLUCOSE
Common Name English
Code System Code Type Description
MERCK INDEX
m5701
Created by admin on Mon Mar 31 20:33:23 GMT 2025 , Edited by admin on Mon Mar 31 20:33:23 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID501317544
Created by admin on Mon Mar 31 20:33:23 GMT 2025 , Edited by admin on Mon Mar 31 20:33:23 GMT 2025
PRIMARY
PUBCHEM
441422
Created by admin on Mon Mar 31 20:33:23 GMT 2025 , Edited by admin on Mon Mar 31 20:33:23 GMT 2025
PRIMARY
CAS
5996-00-9
Created by admin on Mon Mar 31 20:33:23 GMT 2025 , Edited by admin on Mon Mar 31 20:33:23 GMT 2025
PRIMARY
FDA UNII
N2VA1H3TIQ
Created by admin on Mon Mar 31 20:33:23 GMT 2025 , Edited by admin on Mon Mar 31 20:33:23 GMT 2025
PRIMARY