Showing Compound 1,5-Anhydrosorbitol (FDB023050)

Record Information

Version

1.0

Creation date

2011-09-21 00:23:50 UTC

Update date

2015-10-09 22:32:29 UTC

Primary ID

FDB023050

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

1,5-Anhydrosorbitol

Description

1,5-Anhydrosorbitol or 1,5-anhydroglucitol (1,5-AG) is a validated marker of short-term glycemic control. This substance is derived mainly from food, is well absorbed in the intestine, and is distributed to all organs and tissues. It is metabolically stable, being excreted in the urine when its level exceeds the renal threshold. It is reabsorbed in the renal tubules, and is competitively inhibited by glucosuria, which leads to a reduction in its level in serum. The correlation between this reduction and the amount of glucose present in urine is so close that 1,5 AG can be used as a sensitive, day-to-day, real-time marker of glycemic control. It provides useful information on current glycemic control and is superior to both hemoglobin A1C and fructosamine in detecting near-normoglycemia. 1,5-AG in human plasma has been proposed for several years as a short-term, retrospective marker of glycaemic control and seems to be the most suitable parameter for monitoring glucose excursions. The decrease in serum 1,5-AG is very sensitive to urinary glucose excretion. It is a metabolically inert polyol that competes with glucose for reabsorption in the kidneys. Otherwise stable levels of 1,5-AG are rapidly depleted as blood glucose levels exceed the renal threshold for glucosuria. 1,5-AG is also more tightly associated with glucose fluctuations and postprandial glucose. (PMID: 18088226, 12166605, 7783360, 8940824) [HMDB]

CAS Number

154-58-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,5-Anhydro-D-sorbitol	ChEBI
1,5-Anhydroglucitol	ChEBI
1,5-AG	HMDB
1,5-anhydro-D-Glucitol	HMDB
1-Deoxyglucose	MeSH, HMDB
1,5-ANHYDROSORBITOL	ChEBI
Aceritol	MeSH, HMDB
Polygalitol	MeSH, HMDB
1-Deoxy-D-glucose	MeSH, HMDB
1,5-Sorbitan	MeSH, HMDB
1-Deoxy-D-glucopyranose	MeSH, HMDB
1,5-anhydro-D-glucitol	hmdb

Predicted Properties

Property	Value	Source
Water Solubility	1040 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-2.6	ChemAxon
logS	0.8	ALOGPS
pKa (Strongest Acidic)	12.66	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	34.89 m³·mol⁻¹	ChemAxon
Polarizability	15.19 Å³	ChemAxon
Number of Rings	1	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

C6H12O5

IUPAC name

(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-3,4,5-triol

InChI Identifier

InChI=1S/C6H12O5/c7-1-4-6(10)5(9)3(8)2-11-4/h3-10H,1-2H2/t3-,4+,5+,6+/m0/s1

InChI Key

MPCAJMNYNOGXPB-SLPGGIOYSA-N

Isomeric SMILES

OC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O

Average Molecular Weight

164.1565

Monoisotopic Molecular Weight

164.068473494

Classification

Description

Belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharides

Alternative Parents

Substituents

Oxane
Monosaccharide
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

anhydro sugar (CHEBI:16070 )

Ontology

Diabetes mellitus type 2

Disposition

Source:

Endogenous

Biological location:

Organ and components:

Prostate

Subcellular:

Cytoplasm

Biofluid and excreta:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
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
GC-MS	1,5-Anhydrosorbitol, non-derivatized, GC-MS Spectrum	splash10-00kb-0930000000-3e9a279cc11867623df9	Spectrum
GC-MS	1,5-Anhydrosorbitol, non-derivatized, GC-MS Spectrum	splash10-00kb-0930000000-3e9a279cc11867623df9	Spectrum
GC-MS	1,5-Anhydrosorbitol, non-derivatized, GC-MS Spectrum	splash10-0gb9-0900000000-3b72b858c9bcc30c45b1	Spectrum
GC-MS	1,5-Anhydrosorbitol, non-derivatized, GC-MS Spectrum	splash10-0fr2-0920000000-5ad690bbbd7fce791cce	Spectrum
Predicted GC-MS	1,5-Anhydrosorbitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9600000000-614246ddd5b68d2ed62d	Spectrum
Predicted GC-MS	1,5-Anhydrosorbitol, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01di-4169300000-4fef5d885796ecad0f89	Spectrum
Predicted GC-MS	1,5-Anhydrosorbitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-6900000000-9a919af22cbe7d86b80d	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-014i-9100000000-f5cab1c2b02d65ad346a	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-014i-9000000000-ced7163dcc8f3ebdbbce	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0w30-0900000000-7cd7be2b3ef8c9d328e3	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-0900000000-c8a9b1625a999852f120	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-1900000000-60691e9a1518b8f9eacd	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00bi-9200000000-e9e5be081f31a0ee52fd	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-c6502965757c84521bf7	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dj-1900000000-944d7cc4495151774511	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9100000000-eea65e515404cb15787a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-016s-0900000000-11ed18d0db7491144ffd	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-002b-9700000000-5e4a2cbe1835cdf91d56	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4m-9000000000-b6c715de68810d7109e3	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-2900000000-20c29efaf1999d1f7f7d	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0btc-9300000000-d09212a569ed1403170e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-3b59d6f226c5762f52c0	2021-09-25	View Spectrum