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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:05 UTC

Update Date

2023-02-21 17:16:28 UTC

HMDB ID

HMDB0002712

Secondary Accession Numbers

HMDB0011726
HMDB0011736
HMDB02712
HMDB11726
HMDB11736

Metabolite Identification

Common 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 glycemic 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 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	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

Chemical Formula

C₆H₁₂O₅

Average Molecular Weight

164.1565

Monoisotopic Molecular Weight

164.068473494

IUPAC Name

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

Traditional Name

1,5-anhydroglucitol

CAS Registry Number

154-58-5

SMILES

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

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

Chemical Taxonomy

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

Physiological effect

Health effect

Observation

Attachment loss (HMDB: HMDB0002712)
Missing teeth (HMDB: HMDB0002712)

Intervention

Periodontal Probing Depth (HMDB: HMDB0002712)

Endocrine system disorder

Diabetes mellitus type 2 (HMDB: HMDB0002712)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 7859616)
Cerebrospinal Fluid (CSF) (PMID: 8595727)
Saliva (PMID: 22308371)
Cerebrospinal fluid (HMDB: HMDB0002712)

Organ

Prostate (HMDB: HMDB0002712)
Placenta (HMDB: HMDB0002712)

Excreta

Biofluid or Excreta

Sweat (PMID: 26755145)
Urine (PMID: 28157703)

Cellular substructure

Cytoplasm (HMDB: HMDB0002712)

Source

Endogenous

Endogenous (HMDB: HMDB0002712)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Biomarker

Diabetes mellitus type 2 (MarkerDB: MDB00000397)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	142 - 143 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	135.532	31661259
DarkChem	[M-H]-	132.65	31661259
DeepCCS	[M+H]+	136.907	30932474
DeepCCS	[M-H]-	134.612	30932474
DeepCCS	[M-2H]-	169.034	30932474
DeepCCS	[M+Na]+	143.248	30932474
AllCCS	[M+H]+	137.6	32859911
AllCCS	[M+H-H2O]+	133.2	32859911
AllCCS	[M+NH4]+	141.7	32859911
AllCCS	[M+Na]+	142.9	32859911
AllCCS	[M-H]-	130.1	32859911
AllCCS	[M+Na-2H]-	131.4	32859911
AllCCS	[M+HCOO]-	132.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter)). Predicted by Afia on May 17, 2022.	1.23 minutes	32390414
Predicted by Siyang on May 30, 2022	9.5261 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.56 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	269.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	680.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	302.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	41.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	66.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	281.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	234.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	648.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	581.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	43.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	831.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	188.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	220.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	607.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	341.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	321.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,5-Anhydrosorbitol	OC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O	3095.7	Standard polar	33892256
1,5-Anhydrosorbitol	OC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O	1675.6	Standard non polar	33892256
1,5-Anhydrosorbitol	OC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O	1512.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,5-Anhydrosorbitol,1TMS,isomer #1	C[Si](C)(C)OC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O	1584.1	Semi standard non polar	33892256
1,5-Anhydrosorbitol,1TMS,isomer #2	C[Si](C)(C)O[C@H]1CO[C@H](CO)[C@@H](O)[C@@H]1O	1575.1	Semi standard non polar	33892256
1,5-Anhydrosorbitol,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](O)CO[C@H](CO)[C@H]1O	1583.5	Semi standard non polar	33892256
1,5-Anhydrosorbitol,1TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](CO)OC[C@H](O)[C@H]1O	1574.0	Semi standard non polar	33892256
1,5-Anhydrosorbitol,2TMS,isomer #1	C[Si](C)(C)OC[C@H]1OC[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O	1628.6	Semi standard non polar	33892256
1,5-Anhydrosorbitol,2TMS,isomer #2	C[Si](C)(C)OC[C@H]1OC[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O	1642.5	Semi standard non polar	33892256
1,5-Anhydrosorbitol,2TMS,isomer #3	C[Si](C)(C)OC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C	1604.5	Semi standard non polar	33892256
1,5-Anhydrosorbitol,2TMS,isomer #4	C[Si](C)(C)O[C@H]1CO[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	1587.0	Semi standard non polar	33892256
1,5-Anhydrosorbitol,2TMS,isomer #5	C[Si](C)(C)O[C@H]1CO[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	1567.9	Semi standard non polar	33892256
1,5-Anhydrosorbitol,2TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@@H](O)CO[C@H](CO)[C@H]1O[Si](C)(C)C	1585.0	Semi standard non polar	33892256
1,5-Anhydrosorbitol,3TMS,isomer #1	C[Si](C)(C)OC[C@H]1OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	1659.6	Semi standard non polar	33892256
1,5-Anhydrosorbitol,3TMS,isomer #2	C[Si](C)(C)OC[C@H]1OC[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	1693.8	Semi standard non polar	33892256
1,5-Anhydrosorbitol,3TMS,isomer #3	C[Si](C)(C)OC[C@H]1OC[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1668.3	Semi standard non polar	33892256
1,5-Anhydrosorbitol,3TMS,isomer #4	C[Si](C)(C)O[C@H]1CO[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1632.0	Semi standard non polar	33892256
1,5-Anhydrosorbitol,4TMS,isomer #1	C[Si](C)(C)OC[C@H]1OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1782.1	Semi standard non polar	33892256
1,5-Anhydrosorbitol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O	1834.1	Semi standard non polar	33892256
1,5-Anhydrosorbitol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@H](CO)[C@@H](O)[C@@H]1O	1833.3	Semi standard non polar	33892256
1,5-Anhydrosorbitol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)CO[C@H](CO)[C@H]1O	1818.1	Semi standard non polar	33892256
1,5-Anhydrosorbitol,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](CO)OC[C@H](O)[C@H]1O	1812.8	Semi standard non polar	33892256
1,5-Anhydrosorbitol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O	2082.4	Semi standard non polar	33892256
1,5-Anhydrosorbitol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2083.3	Semi standard non polar	33892256
1,5-Anhydrosorbitol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1OC[C@H](O)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2047.9	Semi standard non polar	33892256
1,5-Anhydrosorbitol,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2074.2	Semi standard non polar	33892256
1,5-Anhydrosorbitol,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2068.1	Semi standard non polar	33892256
1,5-Anhydrosorbitol,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)CO[C@H](CO)[C@H]1O[Si](C)(C)C(C)(C)C	2053.1	Semi standard non polar	33892256
1,5-Anhydrosorbitol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	2340.4	Semi standard non polar	33892256
1,5-Anhydrosorbitol,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H]1OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	2352.9	Semi standard non polar	33892256
1,5-Anhydrosorbitol,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H]1OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2323.5	Semi standard non polar	33892256
1,5-Anhydrosorbitol,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2332.2	Semi standard non polar	33892256
1,5-Anhydrosorbitol,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H]1OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2609.2	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Saliva
Sweat
Urine

Tissue Locations

Placenta
Prostate

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	150.0 (140 - 171) uM	Adolescent (13-18 years old)	Female	Normal	17659063	details
Blood	Detected and Quantified	130.0 (95.0 - 178.0) uM	Adolescent (13-18 years old)	Male	Normal	17659063	details
Blood	Detected and Quantified	150.0 (73.0 - 243.0) uM	Adult (>18 years old)	Not Specified	Normal	7859616	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	53.0 (11.0-95.0) uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	110.9 +/- 30.2 uM	Adult (>18 years old)	Both	Normal	8595727	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	25.0 +/- 13.0 uM	Adult (>18 years old)	Both	Normal	18502700	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Sweat	Detected but not Quantified	Not Quantified	Adult	Both	Normal	26755145	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	50.0 (18.5 - 95.0) uM	Adult (>18 years old)	Not Specified	Diabetes	16731998	details
Blood	Detected and Quantified	62.0 +/- 38.0 uM	Adult (>18 years old)	Both	Diabetes	9357814	details
Blood	Detected and Quantified	30.0 (9.7 - 66.4) uM	Adolescent (13-18 years old)	Both	Diabetes	17659063	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Pancreatic Cancer	25429707	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	41.7 +/-13.7 uM	Adult (>18 years old)	Both	Alzheimer's disease	8595727	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Missing teeth	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Diabetes mellitus type 2
Dungan KM, Buse JB, Largay J, Kelly MM, Button EA, Kato S, Wittlin S: 1,5-anhydroglucitol and postprandial hyperglycemia as measured by continuous glucose monitoring system in moderately controlled patients with diabetes. Diabetes Care. 2006 Jun;29(6):1214-9. [PubMed:16731998 ] Stickle D, Turk J: A kinetic mass balance model for 1,5-anhydroglucitol: applications to monitoring of glycemic control. Am J Physiol. 1997 Oct;273(4 Pt 1):E821-30. [PubMed:9357814 ] Nguyen TM, Rodriguez LM, Mason KJ, Heptulla RA: Serum 1,5-anhydroglucitol (Glycomark) levels in children with and without type 1 diabetes mellitus. Pediatr Diabetes. 2007 Aug;8(4):214-9. [PubMed:17659063 ]
Pancreatic cancer
Xie G, Lu L, Qiu Y, Ni Q, Zhang W, Gao YT, Risch HA, Yu H, Jia W: Plasma metabolite biomarkers for the detection of pancreatic cancer. J Proteome Res. 2015 Feb 6;14(2):1195-202. doi: 10.1021/pr501135f. Epub 2014 Dec 8. [PubMed:25429707 ]
Alzheimer's disease
Shetty HU, Holloway HW, Schapiro MB: Cerebrospinal fluid and plasma distribution of myo-inositol and other polyols in Alzheimer disease. Clin Chem. 1996 Feb;42(2):298-302. [PubMed:8595727 ]
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Missing teeth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]

Associated OMIM IDs

125853 (Diabetes mellitus type 2)
260350 (Pancreatic cancer)
104300 (Alzheimer's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

1,5-Anhydroglucitol

METLIN ID

3775

PubChem Compound

64960

PDB ID

Not Available

ChEBI ID

16070

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

MDB00000397

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Shetty HU, Holloway HW, Rapoport SI: Capillary gas chromatography combined with ion trap detection for quantitative profiling of polyols in cerebrospinal fluid and plasma. Anal Biochem. 1995 Jan 1;224(1):279-85. [PubMed:7710082 ]
Servo C, Pitkanen E: Variation in polyol levels in cerebrospinal fluid and serum in diabetic patients. Diabetologia. 1975 Dec;11(6):575-80. [PubMed:1205026 ]
Sode K, Sugiura H, Tsugawa W, Watazu Y, Hamafuji T: Enzyme electrochemical preparation of a 3-keto derivative of 1,5-anhydro-D-glucitol using glucose-3-dehydrogenase. Appl Biochem Biotechnol. 2000 Spring;84-86:947-54. [PubMed:10849848 ]
Yoshioka S, Saitoh S, Fujisawa T, Fujimori A, Takatani O, Funabashi M: Identification and metabolic implication of 1-deoxyglucose (1,5-anhydroglucitol) in human plasma. Clin Chem. 1982 Jun;28(6):1283-6. [PubMed:7074934 ]
Yamanouchi T, Minoda S, Ogata N, Tachibana Y, Sekino N, Miyashita H, Akaoka I: Prolonged hyperalimentation as a possible cause of renal tubular dysfunction: evaluation of 1,5-anhydro-D-glucitol resorption and N-acetylglucosaminidase excretion in humans. Clin Sci (Lond). 1995 Feb;88(2):203-10. [PubMed:7720346 ]
Shetty HU, Holloway HW, Schapiro MB: Cerebrospinal fluid and plasma distribution of myo-inositol and other polyols in Alzheimer disease. Clin Chem. 1996 Feb;42(2):298-302. [PubMed:8595727 ]
Dworacka M, Winiarska H, Szymanska M, Kuczynski S, Szczawinska K, Wierusz-Wysocka B: 1,5-anhydro-D-glucitol: a novel marker of glucose excursions. Int J Clin Pract Suppl. 2002 Jul;(129):40-4. [PubMed:12166605 ]
Akanuma Y, Morita M, Fukuzawa N, Yamanouchi T, Akanuma H: Urinary excretion of 1,5-anhydro-D-glucitol accompanying glucose excretion in diabetic patients. Diabetologia. 1988 Nov;31(11):831-5. [PubMed:3234638 ]
Dungan KM: 1,5-anhydroglucitol (GlycoMark) as a marker of short-term glycemic control and glycemic excursions. Expert Rev Mol Diagn. 2008 Jan;8(1):9-19. [PubMed:18088226 ]
Matsuyama T, Katayama Y, Fujita S: [Recent progress in evaluation of glycemic control by glycated protein and 1,5-AG]. Rinsho Byori. 1995 May;43(5):445-8. [PubMed:7783360 ]
Saito H, Ohtomo T, Inui K: Na(+)-dependent uptake of 1,5-anhydro-D-glucitol via the transport systems for D-glucose and D-mannose in the kidney epithelial cell line, LLC-PK1. Nihon Jinzo Gakkai Shi. 1996 Oct;38(10):435-40. [PubMed:8940824 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details

1. 1,5-anhydro-D-fructose reductase

General function:: Not Available
Specific function:: Catalyzes the NADPH-dependent reduction of 1,5-anhydro-D-fructose (AF) to 1,5-anhydro-D-glucitol. Can also catalyze the reduction of various aldehydes and quinones (By similarity). Has low NADPH-dependent reductase activity towards 9,10-phenanthrenequinone (in vitro).
Gene Name:: AKR1E2
Uniprot ID:: Q96JD6
Molecular weight:: 36588.935

Reactions

1,5-Anhydrosorbitol + NADP → D-1,5-Anhydrofructose + NADPH	details

Showing metabocard for 1,5-Anhydrosorbitol (HMDB0002712)

MOL for HMDB0002712 (1,5-Anhydrosorbitol)

3D MOL for HMDB0002712 (1,5-Anhydrosorbitol)

3D SDF for HMDB0002712 (1,5-Anhydrosorbitol)

3D-SDF for HMDB0002712 (1,5-Anhydrosorbitol)

PDB for HMDB0002712 (1,5-Anhydrosorbitol)

3D PDB for HMDB0002712 (1,5-Anhydrosorbitol)

SMILES for HMDB0002712 (1,5-Anhydrosorbitol)

INCHI for HMDB0002712 (1,5-Anhydrosorbitol)

Structure for HMDB0002712 (1,5-Anhydrosorbitol)

3D Structure for HMDB0002712 (1,5-Anhydrosorbitol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions