ARABINOSE, D-

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C5H10O5
Molecular Weight	150.1299
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=PYMYPHUHKUWMLA-WDCZJNDASA-N

InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4-,5+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C5H10O5
Molecular Weight	150.1299
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17097644 | https://www.ncbi.nlm.nih.gov/pubmed/26791015

D-Arabinose (D-Ara) is a reducing rare sugar. It is a substrate for by D-arabinose dehydrogenase (ARA) and participated in D-erythroascorbic acid synthesis in S. cerevisiae. D-Erythroascorbic acid (eAsA) is an important antioxidant molecule in yeast. It was found, that ARA 2p, not ARA 1p, mainly contributes to the production of eAsA. Recently was published the first report of biological of D-Ara. It was compared the growth inhibitory effects of aldohexose stereoisomers against the animal model Caenorhabditis elegans cultured in monoxenic conditions with Escherichia coli as food. The inhibitory effect of D-Ara was also observed in animals cultured in axenic conditions using a chemically defined medium; this excluded the possible influence of E. coli. Among these stereoisomers, the D-Ara showed particularly strong growth inhibition. The assumption was made pointing, that the inhibition could be induced by multiple mechanisms, for example, disturbance of D-ribose and D-fructose metabolism.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
D-arabinose 1-dehydrogenase 2 Target ID: Q04212 Gene ID: 855057.0 Gene Symbol: ARA2 Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17097644	Substrate 661

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
D-arabinose dehydrogenase and its gene from Saccharomyces cerevisiae.	1998 Dec 8	9920381
NAD+-specific D-arabinose dehydrogenase and its contribution to erythroascorbic acid production in Saccharomyces cerevisiae.	2006 Nov 27	17097644
Growth inhibitory effect of D-arabinose against the nematode Caenorhabditis elegans: Discovery of a novel bioactive monosaccharide.	2016 Feb 1	26791015

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

D-arabinose (D-Ara) showed particularly strong growth inhibition against the nematode Caenorhabditis elegans. The IC50 value for D-Ara was estimated to be 7.5 mM, which surpassed that of the potent glycolytic inhibitor 2-deoxy-D-glucose (19.5 mM) used as a positive control. The inhibitory effect of D-Ara was also observed in animals cultured in axenic conditions using a chemically defined medium; this excluded the possible influence of E. coli.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:00:18 GMT 2023` Edited by `admin` on `Fri Dec 15 16:00:18 GMT 2023`
Record UNII	F0W6ETZ4E5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ARABINOSE, D-

Systematic Name

English

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

Systematic Name

English

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

Systematic Name

English

(3S,4S,5R)-5-(HYDROXYMETHYL)TETRAHYDROFURAN-2,3,4-TRIOL

Systematic Name

English

(-)-ARABINOSE

Systematic Name

English

D-ARABINOSE

Systematic Name

English

D-(-)-ARABINOSE

Systematic Name

English

ARABINOSE D-FORM

Common Name

English

ARABINOSE D-FORM [MI]

Common Name

English

Code System Code Type Description

ECHA (EC/EINECS)

233-708-5