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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:19 UTC

Update Date

2022-03-07 02:49:17 UTC

HMDB ID

HMDB0002917

Secondary Accession Numbers

HMDB02917

Metabolite Identification

Common Name

D-Xylitol

Description

Xylitol is a five-carbon sugar alcohol that is obtained through the diet. It is not endogenously produced by humans. Xylitol is used as a diabetic sweetener which is roughly as sweet as sucrose with 33% fewer calories. Xylitol is naturally found in many fruits (strawberries, plums, raspberries) and vegetables (e.g. cauliflower). Because of fruit and vegetable consumption the human body naturally processes 15 grams of xylitol per day. Xylitol can be produced industrially starting from primary matters rich in xylan which is hydrolyzed to obtain xylose. It is extracted from hemicelluloses present in the corn raids, the almond hulls or the barks of birch (or of the by-products of wood: shavings hard, paper pulp). Of all polyols, it is the one that has the sweetest flavor (it borders that of saccharose). It gives a strong refreshing impression, making xylitol an ingredient of choice for the sugarless chewing gum industry. In addition to his use in confectionery, it is used in the pharmaceutical industry for certain mouthwashes and toothpastes and in cosmetics (creams, soaps, etc.). Xylitol is produced starting from xylose, the isomaltose, by enzymatic transposition of the saccharose (sugar). Xylitol is not metabolized by cariogenic (cavity-causing) bacteria and gum chewing stimulates the flow of saliva; as a result, chewing xylitol gum may prevent dental caries. Chewing xylitol gum for 4 to 14 days reduces the amount of dental plaque. The reduction in the amount of plaque following xylitol gum chewing within 2 weeks may be a transient phenomenon. Chewing xylitol gum for 6 months reduced mutans streptococci levels in saliva and plaque in adults (PMID:17426399 , 15964535 ). Studies have also shown xylitol chewing gum can help prevent acute otitis media (ear aches and infections) as the act of chewing and swallowing assists with the disposal of earwax and clearing the middle ear, while the presence of xylitol prevents the growth of bacteria in the eustachian tubes. Xylitol is well established as a life-threatening toxin to dogs. The number of reported cases of xylitol toxicosis in dogs has significantly increased since the first reports in 2002. Dogs that have ingested foods containing xylitol (greater than 100 milligrams of xylitol consumed per kilogram of bodyweight) have presented with low blood sugar (hypoglycemia), which can be life-threatening. Xylitol is found to be associated with ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2R,3R,4S)-Pentane-1,2,3,4,5-pentaol	ChEBI
Xylit	ChEBI
Xylite	ChEBI
Xylo-pentitol	HMDB
Xylitol	HMDB
D-XYLITOL	ChEBI

Chemical Formula

C₅H₁₂O₅

Average Molecular Weight

152.1458

Monoisotopic Molecular Weight

152.068473494

IUPAC Name

(2R,3r,4S)-pentane-1,2,3,4,5-pentol

Traditional Name

xylitol

CAS Registry Number

87-99-0

SMILES

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

InChI Identifier

InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4+,5+

InChI Key

HEBKCHPVOIAQTA-SCDXWVJYSA-N

Chemical Taxonomy

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

pentitol (CHEBI:17151 )

Ontology

Physiological effect

Organoleptic effect

Odor

Odorless

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 14988808)
Cerebrospinal Fluid (CSF) (PMID: 14988808)
Saliva (PMID: 12097436)

Organ

Prostate (HMDB: HMDB0002917)
Placenta (HMDB: HMDB0002917)

Excreta

Biofluid or Excreta

Urine (PMID: 14988808)
Feces (PMID: 22411374)

Cellular substructure

Cytoplasm (HMDB: HMDB0002917)

Source

Exogenous

Exogenous (HMDB: HMDB0002917)

Food

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Leaf vegetable

Spinach (FooDB: FOOD00178)
Green vegetables (FooDB: FOOD00872)

Onion-family vegetable

Garden onion (FooDB: FOOD00006)

Brassica

Brassicas (FooDB: FOOD00857)

Fruit

Tropical fruit

Papaya (FooDB: FOOD00041)

Berry

Red raspberry (FooDB: FOOD00162)

Fruits (FooDB: FOOD00871)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Xylitol Degradation (PathBank: SMP0002345)

Role

Industrial application

Sweetening agent (HMDB: HMDB0002917)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Diuretic (HMDB: HMDB0002917)

Pharmaceutical industry

Hepatoprotective (HMDB: HMDB0002917)

Digestive system agent

Gastrointestinal agent

Laxative (HMDB: HMDB0002917)

Biomarker

Ribose-5-phosphate isomerase deficiency (MarkerDB: MDB00000406)

Biological role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	93.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	642 mg/mL	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	135.399	30932474
DeepCCS	[M-H]-	133.003	30932474
DeepCCS	[M-2H]-	166.979	30932474
DeepCCS	[M+Na]+	141.598	30932474
AllCCS	[M+H]+	135.8	32859911
AllCCS	[M+H-H2O]+	131.9	32859911
AllCCS	[M+NH4]+	139.5	32859911
AllCCS	[M+Na]+	140.6	32859911
AllCCS	[M-H]-	126.8	32859911
AllCCS	[M+Na-2H]-	129.0	32859911
AllCCS	[M+HCOO]-	131.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
D-Xylitol	OC[C@H](O)[C@@H](O)[C@H](O)CO	2895.7	Standard polar	33892256
D-Xylitol	OC[C@H](O)[C@@H](O)[C@H](O)CO	1750.5	Standard non polar	33892256
D-Xylitol	OC[C@H](O)[C@@H](O)[C@H](O)CO	1486.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
D-Xylitol,1TMS,isomer #1	C[Si](C)(C)OC[C@H](O)[C@@H](O)[C@H](O)CO	1545.5	Semi standard non polar	33892256
D-Xylitol,1TMS,isomer #2	C[Si](C)(C)O[C@@H](CO)[C@@H](O)[C@H](O)CO	1512.2	Semi standard non polar	33892256
D-Xylitol,1TMS,isomer #3	C[Si](C)(C)O[C@H]([C@@H](O)CO)[C@H](O)CO	1495.4	Semi standard non polar	33892256
D-Xylitol,1TMS,isomer #4	C[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O)CO	1512.2	Semi standard non polar	33892256
D-Xylitol,1TMS,isomer #5	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)CO	1545.5	Semi standard non polar	33892256
D-Xylitol,2TMS,isomer #1	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)CO	1586.6	Semi standard non polar	33892256
D-Xylitol,2TMS,isomer #10	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@@H](O)CO	1586.6	Semi standard non polar	33892256
D-Xylitol,2TMS,isomer #2	C[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)CO	1583.3	Semi standard non polar	33892256
D-Xylitol,2TMS,isomer #3	C[Si](C)(C)OC[C@H](O)[C@@H](O)[C@@H](CO)O[Si](C)(C)C	1606.5	Semi standard non polar	33892256
D-Xylitol,2TMS,isomer #4	C[Si](C)(C)OC[C@H](O)[C@@H](O)[C@H](O)CO[Si](C)(C)C	1611.0	Semi standard non polar	33892256
D-Xylitol,2TMS,isomer #5	C[Si](C)(C)O[C@@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)CO	1560.0	Semi standard non polar	33892256
D-Xylitol,2TMS,isomer #6	C[Si](C)(C)O[C@@H](CO)[C@@H](O)[C@@H](CO)O[Si](C)(C)C	1579.4	Semi standard non polar	33892256
D-Xylitol,2TMS,isomer #7	C[Si](C)(C)OC[C@@H](O)[C@H](O)[C@H](CO)O[Si](C)(C)C	1606.5	Semi standard non polar	33892256
D-Xylitol,2TMS,isomer #8	C[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C)[C@@H](O)CO	1560.0	Semi standard non polar	33892256
D-Xylitol,2TMS,isomer #9	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@@H](O)CO	1583.3	Semi standard non polar	33892256
D-Xylitol,3TMS,isomer #1	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)CO	1633.1	Semi standard non polar	33892256
D-Xylitol,3TMS,isomer #10	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@@H](O)CO	1633.1	Semi standard non polar	33892256
D-Xylitol,3TMS,isomer #2	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](CO)O[Si](C)(C)C	1647.8	Semi standard non polar	33892256
D-Xylitol,3TMS,isomer #3	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O)[C@H](O)CO[Si](C)(C)C	1664.4	Semi standard non polar	33892256
D-Xylitol,3TMS,isomer #4	C[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C	1643.4	Semi standard non polar	33892256
D-Xylitol,3TMS,isomer #5	C[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C	1657.8	Semi standard non polar	33892256
D-Xylitol,3TMS,isomer #6	C[Si](C)(C)OC[C@H](O)[C@@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C	1664.4	Semi standard non polar	33892256
D-Xylitol,3TMS,isomer #7	C[Si](C)(C)O[C@@H](CO)[C@@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C	1621.9	Semi standard non polar	33892256
D-Xylitol,3TMS,isomer #8	C[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C)[C@H](CO)O[Si](C)(C)C	1643.4	Semi standard non polar	33892256
D-Xylitol,3TMS,isomer #9	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O)[C@H](CO)O[Si](C)(C)C	1647.8	Semi standard non polar	33892256
D-Xylitol,4TMS,isomer #1	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](CO)O[Si](C)(C)C	1661.8	Semi standard non polar	33892256
D-Xylitol,4TMS,isomer #2	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O)CO[Si](C)(C)C	1681.2	Semi standard non polar	33892256
D-Xylitol,4TMS,isomer #3	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C	1695.2	Semi standard non polar	33892256
D-Xylitol,4TMS,isomer #4	C[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C	1681.2	Semi standard non polar	33892256
D-Xylitol,4TMS,isomer #5	C[Si](C)(C)OC[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H](CO)O[Si](C)(C)C	1661.8	Semi standard non polar	33892256
D-Xylitol,5TMS,isomer #1	C[Si](C)(C)OC[C@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H](CO[Si](C)(C)C)O[Si](C)(C)C	1737.8	Semi standard non polar	33892256
D-Xylitol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O)[C@H](O)CO	1798.2	Semi standard non polar	33892256
D-Xylitol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@@H](O)[C@H](O)CO	1752.5	Semi standard non polar	33892256
D-Xylitol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]([C@@H](O)CO)[C@H](O)CO	1741.0	Semi standard non polar	33892256
D-Xylitol,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O)[C@@H](O)CO	1752.5	Semi standard non polar	33892256
D-Xylitol,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@@H](O)CO	1798.2	Semi standard non polar	33892256
D-Xylitol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)CO	2023.2	Semi standard non polar	33892256
D-Xylitol,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@@H](O)CO	2023.2	Semi standard non polar	33892256
D-Xylitol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO	2031.8	Semi standard non polar	33892256
D-Xylitol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2041.0	Semi standard non polar	33892256
D-Xylitol,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O)[C@H](O)CO[Si](C)(C)C(C)(C)C	2046.5	Semi standard non polar	33892256
D-Xylitol,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO	2032.2	Semi standard non polar	33892256
D-Xylitol,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2024.2	Semi standard non polar	33892256
D-Xylitol,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O)[C@H](CO)O[Si](C)(C)C(C)(C)C	2041.0	Semi standard non polar	33892256
D-Xylitol,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)O[C@H](CO)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CO	2032.2	Semi standard non polar	33892256
D-Xylitol,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CO	2031.8	Semi standard non polar	33892256
D-Xylitol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO	2304.3	Semi standard non polar	33892256
D-Xylitol,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)CO	2304.3	Semi standard non polar	33892256
D-Xylitol,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2313.8	Semi standard non polar	33892256
D-Xylitol,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O)CO[Si](C)(C)C(C)(C)C	2304.0	Semi standard non polar	33892256
D-Xylitol,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2330.8	Semi standard non polar	33892256
D-Xylitol,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO[Si](C)(C)C(C)(C)C	2339.9	Semi standard non polar	33892256
D-Xylitol,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2304.0	Semi standard non polar	33892256
D-Xylitol,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2330.1	Semi standard non polar	33892256
D-Xylitol,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)O[Si](C)(C)C(C)(C)C	2330.8	Semi standard non polar	33892256
D-Xylitol,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H](CO)O[Si](C)(C)C(C)(C)C	2313.8	Semi standard non polar	33892256
D-Xylitol,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO)O[Si](C)(C)C(C)(C)C	2542.6	Semi standard non polar	33892256
D-Xylitol,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)CO[Si](C)(C)C(C)(C)C	2546.4	Semi standard non polar	33892256
D-Xylitol,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2537.1	Semi standard non polar	33892256
D-Xylitol,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2546.4	Semi standard non polar	33892256
D-Xylitol,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](CO)O[Si](C)(C)C(C)(C)C	2542.6	Semi standard non polar	33892256
D-Xylitol,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC[C@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2763.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - D-Xylitol EI-B (Non-derivatized)	splash10-0gb9-0983000000-a3ba95772bec5304c32d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - D-Xylitol GC-EI-TOF (Non-derivatized)	splash10-0gba-0940000000-64e78d1e92fe9d145937	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Xylitol GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dl-9100000000-51c1d4635c9c103902c4	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - D-Xylitol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Xylitol Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-014i-9600000000-42440e0b7d380a297360	2020-02-10	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Xylitol Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-02t9-9000000000-d41bf19405e393c2be01	2020-02-10	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Xylitol Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-02t9-9000000000-3d14b034f5655c90b890	2020-02-10	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - D-Xylitol 35V, Negative-QTOF	splash10-00dl-9000000000-2639d9ab8e6deb561f48	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Xylitol 10V, Positive-QTOF	splash10-0udi-1900000000-4f856d537cc8252ecc47	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Xylitol 20V, Positive-QTOF	splash10-03di-9300000000-403bacad5117a30582df	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Xylitol 40V, Positive-QTOF	splash10-03dl-9000000000-eb879b27e7b182cfe7c0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Xylitol 10V, Negative-QTOF	splash10-0udu-9400000000-3db6454ab3e2315aa744	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Xylitol 20V, Negative-QTOF	splash10-0btl-9200000000-b84c400427c7e44eb4dd	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Xylitol 40V, Negative-QTOF	splash10-0a4l-9000000000-c37624fb31a8cb33b163	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Xylitol 10V, Positive-QTOF	splash10-014i-4900000000-d02566d106f64f56452d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Xylitol 20V, Positive-QTOF	splash10-01ox-9000000000-94760e1883352d4864b5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Xylitol 40V, Positive-QTOF	splash10-0007-9000000000-a22bb5556fa857db4c5c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Xylitol 10V, Negative-QTOF	splash10-0zmr-9500000000-1887747b16d168b09609	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Xylitol 20V, Negative-QTOF	splash10-0a4i-9000000000-83f8fb1c321a951b0e7e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - D-Xylitol 40V, Negative-QTOF	splash10-0a4l-9000000000-ad178d7c96ba63131c18	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2020-02-10	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
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	0.677 (0.572-0.782) uM	Adult (>18 years old)	Both	Normal	7710082	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	2.5 (0.0-5.0) uM	Adolescent (13-18 years old)	Both	Normal	14988808	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0 - 5.0 uM	Adolescent (13-18 years old)	Both	Normal	14988808	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	22944170	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	12097436	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	2.3 (0.9-8.2) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	8.4 (6.0-13.8) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	3.533 +/- 2.400 umol/mmol creatinine	Not Specified	Not Specified	Normal	Geigy Scientific ...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	3.5 +/- 2.37 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	4.9 - 7.0 umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	14988808	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	19616694	details
Urine	Detected and Quantified	16.29 +/- 26.02 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	2026685	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	28157703	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.5 (0.0-5.0) uM	Adolescent (13-18 years old)	Both	Ribose-5-phosphate isomerase deficiency	14988808	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	33 - 96 uM	Adolescent (13-18 years old)	Both	Ribose-5-Phosphate Isomerase Deficiency	14988808	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cryptosporidium infection	22944170	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Urine	Detected and Quantified	15 - 34 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Ribose-5-Phosphate Isomerase Deficiency	14988808	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Hepatocellular carcinoma	19616694	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Ribose-5-phosphate isomerase deficiency
Huck JH, Verhoeven NM, Struys EA, Salomons GS, Jakobs C, van der Knaap MS: Ribose-5-phosphate isomerase deficiency: new inborn error in the pentose phosphate pathway associated with a slowly progressive leukoencephalopathy. Am J Hum Genet. 2004 Apr;74(4):745-51. Epub 2004 Feb 25. [PubMed:14988808 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Hepatocellular carcinoma
Wu H, Xue R, Dong L, Liu T, Deng C, Zeng H, Shen X: Metabolomic profiling of human urine in hepatocellular carcinoma patients using gas chromatography/mass spectrometry. Anal Chim Acta. 2009 Aug 19;648(1):98-104. doi: 10.1016/j.aca.2009.06.033. Epub 2009 Jun 21. [PubMed:19616694 ]

Associated OMIM IDs

608611 (Ribose-5-phosphate isomerase deficiency)
114500 (Colorectal cancer)
114550 (Hepatocellular carcinoma)

External Links

DrugBank ID

DB01904

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001134

KNApSAcK ID

Not Available

Chemspider ID

6646

KEGG Compound ID

C00379

BioCyc ID

XYLITOL

BiGG ID

Not Available

Wikipedia Link

Xylitol

METLIN ID

Not Available

PubChem Compound

6912

PDB ID

Not Available

ChEBI ID

17151

Food Biomarker Ontology

Not Available

VMH ID

XYLT

MarkerDB ID

MDB00000406

Good Scents ID

Not Available

References

Synthesis Reference

Hasumi, Fumihiko; Teshima, Chitoku; Okura, Ichiro. Synthesis of xylitol by reduction of xylulose with the combination of hydrogenase and xylulose reductase. Chemistry Letters (1996), (8), 597-598.

Material Safety Data Sheet (MSDS)

Not Available

General References

Verhoeven NM, Huck JH, Roos B, Struys EA, Salomons GS, Douwes AC, van der Knaap MS, Jakobs C: Transaldolase deficiency: liver cirrhosis associated with a new inborn error in the pentose phosphate pathway. Am J Hum Genet. 2001 May;68(5):1086-92. Epub 2001 Mar 27. [PubMed:11283793 ]
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 ]
Roe FJ: Perspectives in carbohydrate toxicology with special reference to carcinogenicity. Swed Dent J. 1984;8(3):99-111. [PubMed:6592775 ]
Onkenhout W, Groener JE, Verhoeven NM, Yin C, Laan LA: L-Arabinosuria: a new defect in human pentose metabolism. Mol Genet Metab. 2002 Sep-Oct;77(1-2):80-5. [PubMed:12359133 ]
Huck JH, Roos B, Jakobs C, van der Knaap MS, Verhoeven NM: Evaluation of pentitol metabolism in mammalian tissues provides new insight into disorders of human sugar metabolism. Mol Genet Metab. 2004 Jul;82(3):231-7. [PubMed:15234337 ]
Funke G, Lucchini GM, Pfyffer GE, Marchiani M, von Graevenitz A: Characteristics of CDC group 1 and group 1-like coryneform bacteria isolated from clinical specimens. J Clin Microbiol. 1993 Nov;31(11):2907-12. [PubMed:8263175 ]
Yeo SF, Zhang Y, Schafer D, Campbell S, Wong B: A rapid, automated enzymatic fluorometric assay for determination of D-arabinitol in serum. J Clin Microbiol. 2000 Apr;38(4):1439-43. [PubMed:10747122 ]
Yamamoto T, Moriwaki Y, Takahashi S, Suda M, Higashino K: Xylitol-induced increase in the concentration of oxypurines and its mechanism. Int J Clin Pharmacol Ther. 1995 Jun;33(6):360-5. [PubMed:7582389 ]
Sundaram G, Bartlett D: Preventative measures for bulimic patients with dental erosion. Eur J Prosthodont Restor Dent. 2001 Mar;9(1):25-9. [PubMed:11695131 ]
Trahan L, Soderling E, Drean MF, Chevrier MC, Isokangas P: Effect of xylitol consumption on the plaque-saliva distribution of mutans streptococci and the occurrence and long-term survival of xylitol-resistant strains. J Dent Res. 1992 Nov;71(11):1785-91. [PubMed:1401440 ]
Loo CY, Mitrakul K, Voss IB, Hughes CV, Ganeshkumar N: Involvement of an inducible fructose phosphotransferase operon in Streptococcus gordonii biofilm formation. J Bacteriol. 2003 Nov;185(21):6241-54. [PubMed:14563858 ]
Klusmann A, Fleischer W, Waldhaus A, Siebler M, Mayatepek E: Influence of D-arabitol and ribitol on neuronal network activity. J Inherit Metab Dis. 2005;28(6):1181-3. [PubMed:16435225 ]
Restaino L, Frampton EW, Lionberg WC, Becker RJ: A chromogenic plating medium for the isolation and identification of Enterobacter sakazakii from foods, food ingredients, and environmental sources. J Food Prot. 2006 Feb;69(2):315-22. [PubMed:16496571 ]
Hauschildt S, Chalmers RA, Lawson AM, Schultis K, Watts RW: Metabolic investigations after xylitol infusion in human subjects. Am J Clin Nutr. 1976 Mar;29(3):258-73. [PubMed:176881 ]
Wang YM, van Eys J: Nutritional significance of fructose and sugar alcohols. Annu Rev Nutr. 1981;1:437-75. [PubMed:6821187 ]
Ylikahri RH, Leino T: Metabolic interactions of xylitol and ethanol in healthy males. Metabolism. 1979 Jan;28(1):25-9. [PubMed:759823 ]
Sestoft L, Gammeltoft A: The effect of intravenous xylitol on the concentration of adenine nucleotides in human liver. Biochem Pharmacol. 1976 Dec 1;25(23):2619-21. [PubMed:985582 ]
Haresaku S, Hanioka T, Tsutsui A, Yamamoto M, Chou T, Gunjishima Y: Long-term effect of xylitol gum use on mutans streptococci in adults. Caries Res. 2007;41(3):198-203. [PubMed:17426399 ]
Grillaud M, Bandon D, Nancy J, Delbos Y, Vaysse F: [The polyols in pediatric dentistry: advantages of xylitol]. Arch Pediatr. 2005 Jul;12(7):1180-6. [PubMed:15964535 ]
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. Aldose reductase

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:: AKR1B1
Uniprot ID:: P15121
Molecular weight:: 35853.125

Reactions

D-Xylitol + NADP → D-Xylose + NADPH + Hydrogen Ion	details

Enzyme Details

2. L-xylulose reductase

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the NADPH-dependent reduction of several pentoses, tetroses, trioses, alpha-dicarbonyl compounds and L-xylulose. Participates in the uronate cycle of glucose metabolism. May play a role in the water absorption and cellular osmoregulation in the proximal renal tubules by producing xylitol, an osmolyte, thereby preventing osmolytic stress from occurring in the renal tubules.
Gene Name:: DCXR
Uniprot ID:: Q7Z4W1
Molecular weight:: 25742.665

Reactions

D-Xylitol + NADP → L-Xylulose + NADPH	details
D-Xylitol + NADP → L-Xylulose + NADPH + Hydrogen Ion	details

Enzyme Details

3. Aldo-keto reductase family 1 member B10

General function:: Not Available
Specific function:: Acts as all-trans-retinaldehyde reductase. Can efficiently reduce aliphatic and aromatic aldehydes, and is less active on hexoses (in vitro). May be responsible for detoxification of reactive aldehydes in the digested food before the nutrients are passed on to other organs.
Gene Name:: AKR1B10
Uniprot ID:: O60218
Molecular weight:: Not Available

Reactions

D-Xylitol + NADP → D-Xylose + NADPH + Hydrogen Ion	details

Showing metabocard for D-Xylitol (HMDB0002917)

MOL for HMDB0002917 (D-Xylitol)

3D MOL for HMDB0002917 (D-Xylitol)

3D SDF for HMDB0002917 (D-Xylitol)

3D-SDF for HMDB0002917 (D-Xylitol)

PDB for HMDB0002917 (D-Xylitol)

3D PDB for HMDB0002917 (D-Xylitol)

SMILES for HMDB0002917 (D-Xylitol)

INCHI for HMDB0002917 (D-Xylitol)

Structure for HMDB0002917 (D-Xylitol)

3D Structure for HMDB0002917 (D-Xylitol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions