RHAMNOSE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H12O5
Molecular Weight	164.1565
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O

InChI

InChIKey=PNNNRSAQSRJVSB-BXKVDMCESA-N

InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4-,5-,6-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://doi.org/10.1016/0022-0981(91)90007-J | https://www.drugbank.ca/drugs/DB02961 | Golan, David E., ed. (2005). 'Chapter 35 - Pharmacology of the Bacterial Cell Wall'. Principles of Pharmacology: The Pathophysiologic Basis of Drug Therapy. Armen H. Tashjian Jr., Ehrin J. Armstrong, Joshua N. Galanter, April Wang Armstrong, Ramy A. Arnaout, Harris S. Rose. Lippincott Williams and Wilkins. p. 569. ISBN 0-7817-4678-7

Rhamnose is a naturally occurring deoxy sugar which can be classified as either a methyl-pentose or a 6-deoxy-hexose. Unlike most other naturally occurring sugars rhamnose is found in nature as L-rhamnose. Rhamnose can be isolated from plants such as Buckthorn, poison sumac, and those of the genus Uncaria. It is also produced by microalgae from class Bacillariophyceae. Throughout nature, rhamnose is commonly bound to other sugars. It is a common glycone component of glycosides in many plants. It also forms a component of the outer cell membrane in acid-fast bacteria of the genus Mycobaterium, including tuberculosis.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
The metabolism of L-rhamnose in animal tissues.	1965	5855461
Inhibition of cyclic AMP-dependent induction of ornithine aminotransferase by simple carbohydrates in cultured hepatocytes.	1987 Dec	2827574
The effect of intestinal hypoperfusion on intestinal absorption and permeability during cardiopulmonary bypass.	1994 Feb	8299899
Use of Presumpto Plates to identify anaerobic bacteria.	1995 May	7615728
Rapid and simultaneous quantification of rhamnose, mannitol, and lactulose in urine by HPLC for estimating intestinal permeability in pediatric practice.	1996 Jan	8565237
Lipopolysaccharide inner core oligosaccharide structure and outer membrane stability in human pathogens belonging to the Enterobacteriaceae.	2005	15949142
Molecular analysis of the genes involved in the biosynthesis of serotype specific polysaccharide in the novel serotype k strains of Streptococcus mutans.	2005 Oct	16101966
L-rhamnose is often an important part of immunodominant epitope for pneumococcal serotype 23F polysaccharide antibodies in human sera immunized with PPV23.	2013	24391831
Rhamnose glycoconjugates for the recruitment of endogenous anti-carbohydrate antibodies to tumor cells.	2014 Jul 7	24909955

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Name

Type

Language

RHAMNOSE

Official Name

English

RHAMNOSE [MI]

Common Name

English

L-RHAMNOSE

Common Name

English

L-(+)-RHAMNOSE

Common Name

English

NSC-2056

Code

English

NSC-287050

Code

English

L-RHAMNOSE [FHFI]

Common Name

English

Rhamnose [WHO-DD]

Common Name

English

(2R,3R,4S,5S)-2,3,4,5-TETRAHYDROXYHEXANAL

Systematic Name

English

RHAMNOSE [INCI]

Common Name

English

(3R,4R,5R,6S)-6-METHYLTETRAHYDRO-2H-PYRAN-2,3,4,5-TETRAOL

Systematic Name

English

FEMA NO. 3730

Code

English

RHAMNOSE, L-

Common Name

English

ISODULCIT

Common Name

English

RHAMNOSE [MART.]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C68484