U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C5H10O5
Molecular Weight 150.1299
Optical Activity ( + / - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ARABINOSE, DL-

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

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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
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)
Substrate
661
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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
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 Sat Dec 16 07:54:09 UTC 2023
Edited
by admin
on Sat Dec 16 07:54:09 UTC 2023
Record UNII
509X20752R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARABINOSE, DL-
Systematic Name English
ARABINOSE [MI]
Common Name English
ARABINOSE, (±)-
Systematic Name English
ARABINOSE [USP-RS]
Common Name English
(±)-ARABINOSE
Systematic Name English
ARABINOSE
INCI   MI  
INCI  
Official Name English
ARABINOSE [INCI]
Common Name English
Classification Tree Code System Code
DSLD 3460 (Number of products:4)
Created by admin on Sat Dec 16 07:54:10 UTC 2023 , Edited by admin on Sat Dec 16 07:54:10 UTC 2023
LOINC 79281-2
Created by admin on Sat Dec 16 07:54:10 UTC 2023 , Edited by admin on Sat Dec 16 07:54:10 UTC 2023
NCI_THESAURUS C68484
Created by admin on Sat Dec 16 07:54:10 UTC 2023 , Edited by admin on Sat Dec 16 07:54:10 UTC 2023
Code System Code Type Description
MERCK INDEX
m2020
Created by admin on Sat Dec 16 07:54:10 UTC 2023 , Edited by admin on Sat Dec 16 07:54:10 UTC 2023
PRIMARY Merck Index
CHEBI
22599
Created by admin on Sat Dec 16 07:54:10 UTC 2023 , Edited by admin on Sat Dec 16 07:54:10 UTC 2023
PRIMARY
FDA UNII
509X20752R
Created by admin on Sat Dec 16 07:54:10 UTC 2023 , Edited by admin on Sat Dec 16 07:54:10 UTC 2023
PRIMARY
CAS
147-81-9
Created by admin on Sat Dec 16 07:54:10 UTC 2023 , Edited by admin on Sat Dec 16 07:54:10 UTC 2023
PRIMARY
PUBCHEM
66308
Created by admin on Sat Dec 16 07:54:10 UTC 2023 , Edited by admin on Sat Dec 16 07:54:10 UTC 2023
PRIMARY
EPA CompTox
DTXSID8041610
Created by admin on Sat Dec 16 07:54:10 UTC 2023 , Edited by admin on Sat Dec 16 07:54:10 UTC 2023
PRIMARY
SMS_ID
100000130672
Created by admin on Sat Dec 16 07:54:10 UTC 2023 , Edited by admin on Sat Dec 16 07:54:10 UTC 2023
PRIMARY
RS_ITEM_NUM
1042055
Created by admin on Sat Dec 16 07:54:10 UTC 2023 , Edited by admin on Sat Dec 16 07:54:10 UTC 2023
PRIMARY
WIKIPEDIA
Arabinose
Created by admin on Sat Dec 16 07:54:10 UTC 2023 , Edited by admin on Sat Dec 16 07:54:10 UTC 2023
PRIMARY
EVMPD
SUB43309
Created by admin on Sat Dec 16 07:54:10 UTC 2023 , Edited by admin on Sat Dec 16 07:54:10 UTC 2023
PRIMARY
NCI_THESAURUS
C68485
Created by admin on Sat Dec 16 07:54:10 UTC 2023 , Edited by admin on Sat Dec 16 07:54:10 UTC 2023
PRIMARY NCIT
ECHA (EC/EINECS)
205-699-8
Created by admin on Sat Dec 16 07:54:10 UTC 2023 , Edited by admin on Sat Dec 16 07:54:10 UTC 2023
PRIMARY
Related Record Type Details
Structure of ARABINOSE, D-
ENANTIOMER -> RACEMATE
Structure of ARABINOSE, L-
ENANTIOMER -> RACEMATE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966