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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 of ARABINOSE, D-

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

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q04212
Gene ID: 855057.0
Gene Symbol: ARA2
Target Organism: Saccharomyces cerevisiae (strain ATCC 204508 / S288c) (Baker's yeast)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
D-arabinose dehydrogenase and its gene from Saccharomyces cerevisiae.
1998 Dec 8
Growth inhibitory effect of D-arabinose against the nematode Caenorhabditis elegans: Discovery of a novel bioactive monosaccharide.
2016 Feb 1

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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
  • Download
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
MI  
Common Name English
ARABINOSE D-FORM [MI]
Common Name English
Code System Code Type Description
ECHA (EC/EINECS)
233-708-5
Created by admin on Fri Dec 15 16:00:18 GMT 2023 , Edited by admin on Fri Dec 15 16:00:18 GMT 2023
PRIMARY
CAS
41546-26-3
Created by admin on Fri Dec 15 16:00:18 GMT 2023 , Edited by admin on Fri Dec 15 16:00:18 GMT 2023
ALTERNATIVE
CAS
10323-20-3
Created by admin on Fri Dec 15 16:00:18 GMT 2023 , Edited by admin on Fri Dec 15 16:00:18 GMT 2023
PRIMARY
PUBCHEM
66308
Created by admin on Fri Dec 15 16:00:18 GMT 2023 , Edited by admin on Fri Dec 15 16:00:18 GMT 2023
PRIMARY
CHEBI
46983
Created by admin on Fri Dec 15 16:00:18 GMT 2023 , Edited by admin on Fri Dec 15 16:00:18 GMT 2023
PRIMARY
CHEBI
17108
Created by admin on Fri Dec 15 16:00:18 GMT 2023 , Edited by admin on Fri Dec 15 16:00:18 GMT 2023
PRIMARY
CAS
28697-53-2
Created by admin on Fri Dec 15 16:00:18 GMT 2023 , Edited by admin on Fri Dec 15 16:00:18 GMT 2023
ALTERNATIVE
EPA CompTox
DTXSID70858954
Created by admin on Fri Dec 15 16:00:18 GMT 2023 , Edited by admin on Fri Dec 15 16:00:18 GMT 2023
PRIMARY
FDA UNII
F0W6ETZ4E5
Created by admin on Fri Dec 15 16:00:18 GMT 2023 , Edited by admin on Fri Dec 15 16:00:18 GMT 2023
PRIMARY
CHEBI
46994
Created by admin on Fri Dec 15 16:00:18 GMT 2023 , Edited by admin on Fri Dec 15 16:00:18 GMT 2023
PRIMARY
MERCK INDEX
m2020
Created by admin on Fri Dec 15 16:00:18 GMT 2023 , Edited by admin on Fri Dec 15 16:00:18 GMT 2023
PRIMARY Merck Index
Related Record Type Details
RACEMATE -> ENANTIOMER
Related Record Type Details
ACTIVE MOIETY