Showing Compound D-Arabitol (FDB001475)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:59 UTC

Update date

2019-11-26 02:56:30 UTC

Primary ID

FDB001475

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

D-Arabitol

Description

D-Arabitol is a polyol. Polyols are sugar alcohols linked to the pentose phosphate pathway (PPP). They are classified on the basis of the number of carbon atoms. Polyols occur in body fluids. A patient with leukoencephalopathy and peripheral neuropathy has been identified as suffering from ribose-5-phosphate isomerase (RPI) deficiency, a defect in the PPP. In this disorder, highly elevated concentrations of the C5 polyols such as D-arabitol are found in body fluids. In addition, transaldolase deficiency, another defect in the PPP, has been diagnosed in a patient with mainly liver problems among others had increased concentrations of polyols, mainly D-arabitol. So far, the pathophysiological role of polyols is relatively unknown. It is thought that D-arabitol is a metabolic end-product in humans. The strong brain-CSF-plasma gradient of polyols in the patient with RPI deficiency suggested a primary metabolic disorder. The mechanisms of brain and neuronal damage in RPI deficiency remain to be elucidated. A neurotoxic effect due to accumulation of the polyols may play a role. D-Arabitol is a product of the enzyme D-arabinitol 4-dehydrogenase (EC 1.1.1.11) in the Pentose and glucuronate interconversion pathway. (PMID: 16435225, J Inherit Metab Dis. 2005;28(6):1181-3).

CAS Number

488-82-4

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Klinit	Kegg
Arabitol	MeSH
Lyxitol	MeSH
D-Arabinitol	MeSH
L-Arabinitol	MeSH
DL-Arabitol	MeSH
(+--)-Arabitol	MeSH
Arabitol, (D)-isomer	MeSH
Arabitol, (L)-isomer	MeSH
Arabino-pentitol	MeSH
D-(+)-Arabitol	HMDB
D-Arabinol	HMDB
D-Lyxitol	HMDB
Arabinitol	biospider
Arabinitol, d-	biospider
Arabitol, (d)	biospider
Arabitol, d-	biospider
D-(+)-arabinitol	biospider
D-(+)-arabitol	biospider
D-arabinitol	biospider
D-arabinol	biospider
D-lyxitol	biospider

Predicted Properties

Property	Value	Source
Water Solubility	664 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-3.1	ChemAxon
logS	0.64	ALOGPS
pKa (Strongest Acidic)	12.76	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	101.15 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	32.44 m³·mol⁻¹	ChemAxon
Polarizability	14.42 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C5H12O5

IUPAC name

pentane-1,2,3,4,5-pentol

InChI Identifier

InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2

InChI Key

HEBKCHPVOIAQTA-UHFFFAOYSA-N

Isomeric SMILES

OCC(O)C(O)C(O)CO

Average Molecular Weight

152.1458

Monoisotopic Molecular Weight

152.068473494

Classification

Description

Belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar alcohols

Alternative Parents

Substituents

Sugar alcohol
Monosaccharide
Secondary alcohol
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

a sugar alcohol (XYLITOL )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	101-104 oC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-01vo-9000000000-f065454e8412613f8ecd	2015-03-01	View Spectrum
Predicted GC-MS	D-Arabitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03dl-9100000000-738016d8bd07caed9ccc	Spectrum
Predicted GC-MS	D-Arabitol, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-6033900000-a5ac27dc62580d112ccd	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-01ba-9500000000-67233150807800e941f0	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-01b9-9000000000-1ff17a8b87bbab9a3622	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-044i-9000000000-e0e330c8a899be718f60	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00m0-2900000000-c6b1101b88fa522fabd0	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0zmr-9500000000-164d598431954fc1aeae	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-0uki-9600000000-b90e9cee04cd0631b599	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-00e9-2900000000-75413a29e8c6b3d9a6a1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0udi-0900000000-c5cc931b9156365c4ca7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-0a5a-0900000000-94cf956e3f47a633d572	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-03k9-0900000000-f0634d5b1d1f523b3caa	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-88c39e799daf7fb9dbca	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9300000000-66487a26d7047f9096a9	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9000000000-514c2ae8b98eb4994147	2015-05-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udu-9400000000-b3ca0d23907878fbe1a8	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0btl-9200000000-92a36674373a271da867	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0btc-9000000000-5e7378c18473f8226282	2015-05-27	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum