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

Molecular Formula	C6H12O5
Molecular Weight	164.1565
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Glucose and citrate reduce the permeability changes caused by indomethacin in humans.	1992 May	1568563
Rapid and simultaneous quantification of rhamnose, mannitol, and lactulose in urine by HPLC for estimating intestinal permeability in pediatric practice.	1996 Jan	8565237
Detection of beta-ureidopropionase deficiency with HPLC-electrospray tandem mass spectrometry and confirmation of the defect at the enzyme level.	2001 Dec	11804209
Platelet aggregation induced by serotype polysaccharides from Streptococcus mutans.	2004 May	15102769
Lipopolysaccharide inner core oligosaccharide structure and outer membrane stability in human pathogens belonging to the Enterobacteriaceae.	2005	15949142
Glutamine supplementation of parenteral nutrition does not improve intestinal permeability, nitrogen balance, or outcome in newborns and infants undergoing digestive-tract surgery: results from a double-blind, randomized, controlled trial.	2005 Apr	15798461
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
Enzymatic Synthesis of Rhamnose Containing Chemicals by Reverse Hydrolysis.	2015	26505759

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:22:25 GMT 2023` Edited by `admin` on `Fri Dec 15 18:22:25 GMT 2023`
Record UNII	QN34XC755A
Record Status	`Validated (UNII)`
Record Version

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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