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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-10-13 04:30:02 UTC

HMDB ID

HMDB0000646

Secondary Accession Numbers

HMDB0000487
HMDB00487
HMDB0062088
HMDB00646
HMDB62088

Metabolite Identification

Common Name

L-Arabinose

Description

L-Arabinose (CAS: 5328-37-0) belongs to the class of compounds known as aldopentoses. An aldopentose is a monosaccharide containing five carbon atoms, including an aldehyde (CHO) functional group. Arabinose gets its name from gum arabic, from which it was first isolate. Most saccharides found in nature are in the "D"-form, however, L-arabinose is in fact more common than D-arabinose. L-arabinose is found in nature as a component of biopolymers such as hemicellulose and pectin. L-arabinose is found in all organisms from bacteria to plants to animals. Arabinose is the second most abundant pentose in lignocellulosic biomass after xylose. There are two different arabinose utilization pathways in nature: bacterial and fungal. The bacterial pathway converts arabinose into xylulose-5-P via ribulose-5-P using three enzymes (L-arabinose isomerase, L-ribulokinase, and L-ribulose-5-P 4-epimerase) after which it enters the pentose phosphate pathway for ethanol production. The fungal pathway converts arabinose into L-arabinitol by aldose reductase (AR) or XR, L-xylulose by L-arabinitol 4-dehydrogenase (LAD), xylitol by L-xylulose reductase (LXR), D-xylulose by xylulose dehydrogenase (XDH), and D-xylulose-5-P by xylulose kinase (XK), and lastly enters the nonoxidative pentose phosphate pathway for further metabolism. Arabinose has a sweet taste and is one of the most abundant components released by complete hydrolysis of non-starch polysaccharides (NSP) of vegetable origin. Although widely present in nature, L-arabinose is rarely used in food production or food flavoring, and its physiological effects in vivo have received little attention. L-arabinose is known to selectively inhibit intestinal sucrase activity in a non-competitive manner. Sucrase is the enzyme that breaks down sucrose into glucose and fructose in the small intestine. As a result, L-arabinose suppresses plasma glucose increase due to sucrose ingestion. The presence of arabinose in urine may indicate overgrowth of intestinal yeast such as Candida albicans or other yeast/fungus species. L-arabinose is also a microbial metabolite found in, and produced by, Mycobacterium (PMID: 16232643 ). In a rare case of two autistic brothers that were not associated with any known metabolic disease, it was found the median value for L-arabinose in their urine samples was 179 umol/mmol creatinine, nearly six times greater than normal children (PMID: 11238761 , 8931641 , 1390604 , 7628083 ).

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
BETA-L-ARABINOSE	ChEBI
WURCS=2.0/1,1,0/[a211h-1b_1-5]/1/	ChEBI
b-L-ARABINOSE	Generator
Β-L-arabinose	Generator
b-L-Arabinopyranose	HMDB
Β-L-arabinopyranose	HMDB
L-Arabinopyranose	HMDB
Pectinose	HMDB
beta-L-Arabinopyranose	HMDB
Arabinopyranose	HMDB
Arabinose	HMDB
L-Arabinose	HMDB

Chemical Formula

C₅H₁₀O₅

Average Molecular Weight

150.1299

Monoisotopic Molecular Weight

150.05282343

IUPAC Name

(2S,3R,4S,5S)-oxane-2,3,4,5-tetrol

Traditional Name

β-L-arabinopyranose

CAS Registry Number

7296-56-2

SMILES

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

InChI Identifier

InChI=1S/C5H10O5/c6-2-1-10-5(9)4(8)3(2)7/h2-9H,1H2/t2-,3-,4+,5-/m0/s1

InChI Key

SRBFZHDQGSBBOR-KLVWXMOXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentoses

Alternative Parents

Substituents

Pentose monosaccharide
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

L-arabinopyranose (CHEBI:40886 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 14988808)
Cerebrospinal Fluid (CSF) (PMID: 12359133)

Organ

Prostate (HMDB: HMDB0000646)

Excreta

Biofluid or Excreta

Urine (PMID: 14988808)
Feces (PMID: 27543620)

Cellular substructure

Extracellular (HMDB: HMDB0000646)

Source

Exogenous

Exogenous (HMDB: HMDB0000646)

Food

Animal origin

Poultry

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)

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Nut

Almond (FooDB: FOOD00148)

Vegetable

Root vegetable

Red beetroot (FooDB: FOOD00264)

Leaf vegetable

Garden cress (FooDB: FOOD00099)

Other vegetable

Horseradish tree (FooDB: FOOD00379)

Herb and spice

Oilseed crop

Flaxseed (FooDB: FOOD00101)

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Fruit

Drupe

Peach (FooDB: FOOD00149)

Pome

Quince (FooDB: FOOD00069)

Endogenous

Endogenous (HMDB: HMDB0000646)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

L-Arabinose Degradation I (PathBank: SMP0002115)

Role

Industrial application

Pharmaceutical industry

Biomarker

Ribose-5-phosphate isomerase deficiency (MarkerDB: MDB00000207)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	158 - 160 °C	Not Available
Boiling Point	415.00 to 416.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	500 mg/mL	Not Available
LogP	-3.02	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1220 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-2.3	ChemAxon
logS	0.91	ALOGPS
pKa (Strongest Acidic)	11.31	ChemAxon
pKa (Strongest Basic)	-3.5	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	0	ChemAxon
Refractivity	29.96 m³·mol⁻¹	ChemAxon
Polarizability	13.37 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
DeepCCS	[M+H]+	135.367	30932474
DeepCCS	[M-H]-	133.163	30932474
DeepCCS	[M-2H]-	167.905	30932474
DeepCCS	[M+Na]+	141.982	30932474
AllCCS	[M+H]+	134.2	32859911
AllCCS	[M+H-H2O]+	129.6	32859911
AllCCS	[M+NH4]+	138.4	32859911
AllCCS	[M+Na]+	139.7	32859911
AllCCS	[M-H]-	124.8	32859911
AllCCS	[M+Na-2H]-	126.5	32859911
AllCCS	[M+HCOO]-	128.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-Arabinose	O[C@H]1CO[C@H](O)[C@H](O)[C@H]1O	3000.0	Standard polar	33892256
L-Arabinose	O[C@H]1CO[C@H](O)[C@H](O)[C@H]1O	1530.6	Standard non polar	33892256
L-Arabinose	O[C@H]1CO[C@H](O)[C@H](O)[C@H]1O	1384.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-Arabinose,1TMS,isomer #1	C[Si](C)(C)O[C@H]1CO[C@H](O)[C@H](O)[C@H]1O	1494.4	Semi standard non polar	33892256
L-Arabinose,1TMS,isomer #2	C[Si](C)(C)O[C@H]1OC[C@H](O)[C@H](O)[C@H]1O	1456.1	Semi standard non polar	33892256
L-Arabinose,1TMS,isomer #3	C[Si](C)(C)O[C@H]1[C@@H](O)OC[C@H](O)[C@@H]1O	1492.8	Semi standard non polar	33892256
L-Arabinose,1TMS,isomer #4	C[Si](C)(C)O[C@H]1[C@@H](O)CO[C@H](O)[C@@H]1O	1501.0	Semi standard non polar	33892256
L-Arabinose,2TMS,isomer #1	C[Si](C)(C)O[C@H]1CO[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O	1519.1	Semi standard non polar	33892256
L-Arabinose,2TMS,isomer #2	C[Si](C)(C)O[C@H]1CO[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O	1515.9	Semi standard non polar	33892256
L-Arabinose,2TMS,isomer #3	C[Si](C)(C)O[C@H]1CO[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	1471.6	Semi standard non polar	33892256
L-Arabinose,2TMS,isomer #4	C[Si](C)(C)O[C@H]1[C@@H](O)CO[C@H](O[Si](C)(C)C)[C@@H]1O	1518.4	Semi standard non polar	33892256
L-Arabinose,2TMS,isomer #5	C[Si](C)(C)O[C@H]1OC[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C	1477.7	Semi standard non polar	33892256
L-Arabinose,2TMS,isomer #6	C[Si](C)(C)O[C@H]1[C@@H](O)CO[C@H](O)[C@@H]1O[Si](C)(C)C	1495.9	Semi standard non polar	33892256
L-Arabinose,3TMS,isomer #1	C[Si](C)(C)O[C@H]1CO[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O	1548.5	Semi standard non polar	33892256
L-Arabinose,3TMS,isomer #2	C[Si](C)(C)O[C@H]1CO[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C	1560.9	Semi standard non polar	33892256
L-Arabinose,3TMS,isomer #3	C[Si](C)(C)O[C@H]1CO[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1553.8	Semi standard non polar	33892256
L-Arabinose,3TMS,isomer #4	C[Si](C)(C)O[C@H]1[C@@H](O)CO[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	1576.0	Semi standard non polar	33892256
L-Arabinose,4TMS,isomer #1	C[Si](C)(C)O[C@H]1CO[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1645.4	Semi standard non polar	33892256
L-Arabinose,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@H](O)[C@H](O)[C@H]1O	1744.5	Semi standard non polar	33892256
L-Arabinose,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1OC[C@H](O)[C@H](O)[C@H]1O	1707.1	Semi standard non polar	33892256
L-Arabinose,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)OC[C@H](O)[C@@H]1O	1726.7	Semi standard non polar	33892256
L-Arabinose,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)CO[C@H](O)[C@@H]1O	1732.8	Semi standard non polar	33892256
L-Arabinose,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O	1990.7	Semi standard non polar	33892256
L-Arabinose,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	1979.0	Semi standard non polar	33892256
L-Arabinose,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	1956.2	Semi standard non polar	33892256
L-Arabinose,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)CO[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O	1976.0	Semi standard non polar	33892256
L-Arabinose,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)O[C@H]1OC[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	1949.6	Semi standard non polar	33892256
L-Arabinose,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)CO[C@H](O)[C@@H]1O[Si](C)(C)C(C)(C)C	1958.4	Semi standard non polar	33892256
L-Arabinose,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2238.9	Semi standard non polar	33892256
L-Arabinose,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2254.8	Semi standard non polar	33892256
L-Arabinose,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@H]1CO[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2250.2	Semi standard non polar	33892256
L-Arabinose,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)CO[C@H](O[Si](C)(C)C(C)(C)C)[C@@H]1O[Si](C)(C)C(C)(C)C	2239.3	Semi standard non polar	33892256
L-Arabinose,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H]1CO[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	2479.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-9400000000-f20d1c35a7eeea1609a5	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_4_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-Arabinose GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Arabinose 10V, Positive-QTOF	splash10-0ue9-0900000000-4856e933b915ddbb0554	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Arabinose 20V, Positive-QTOF	splash10-0f89-0900000000-79e8278d7ae6b34a7772	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Arabinose 40V, Positive-QTOF	splash10-08os-9100000000-64c106194d5825a11d36	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Arabinose 10V, Negative-QTOF	splash10-0002-1900000000-988a7d2dad8bc555d502	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Arabinose 20V, Negative-QTOF	splash10-000t-2900000000-31127350481e63c82ff7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Arabinose 40V, Negative-QTOF	splash10-0006-9000000000-264c06bc93b8e518bbfb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Arabinose 10V, Negative-QTOF	splash10-0002-7900000000-524214992b29f1ff9b80	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Arabinose 20V, Negative-QTOF	splash10-0a4i-9000000000-f758a7d33dac04b06275	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Arabinose 40V, Negative-QTOF	splash10-0a4l-9000000000-4b3e154b12c2ee07bf58	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Arabinose 10V, Positive-QTOF	splash10-0gc0-1900000000-e784a3fdca89dcb59c12	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Arabinose 20V, Positive-QTOF	splash10-0m4p-9100000000-fc295e2732f55a0a18c1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-Arabinose 40V, Positive-QTOF	splash10-0007-9000000000-ba5f29c2c79df8d0956f	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2020-07-08	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2020-07-08	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Urine

Tissue Locations

Prostate

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.5 (0.0-5.0) uM	Adult (>18 years old)	Both	Normal	14988808	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	19.5 (8.0-38.0) uM	Adult (>18 years old)	Both	Normal	12359133	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	8.8 (8.0-31.0) uM	Adult (>18 years old)	Both	Normal	12359133	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	25985090	details
Urine	Detected and Quantified	8.8 (0.8-19.4) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	8.75 (6.12-11.84) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	27.483 +/- 18.288 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	13.3 (1.3-22.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	3.0 (0.0-7.0) uM	Adult (>18 years old)	Both	Ribose-5-phosphate isomerase deficiency	14988808	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	92.0 (66.0-135.0) uM	Children (1-13 years old)	Both	Ribose-5-phosphate isomerase deficiency	14988808	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Urine	Detected and Quantified	17.07 +/- 14.128 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	38.0 (37.0-41.0) umol/mmol creatinine	Adult (>18 years old)	Both	Ribose-5-phosphate isomerase deficiency	14988808	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
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 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

608611 (Ribose-5-phosphate isomerase deficiency)
114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Arabinose

METLIN ID

Not Available

PubChem Compound

439764

PDB ID

Not Available

ChEBI ID

40886

Food Biomarker Ontology

Not Available

VMH ID

ARAB_L

MarkerDB ID

MDB00000207

Good Scents ID

rw1006871

References

Synthesis Reference

Whistler, Roy L.; Schweiger, Richard. Preparation of D-arabinose from D-glucose with hypochlorite. Journal of the American Chemical Society (1959), 81 5190-2.

Material Safety Data Sheet (MSDS)

Not Available

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 ]
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 ]
Lobley RW, Burrows PC, Warwick R, Dawson DJ, Holmes R: Simultaneous assessment of intestinal permeability and lactose tolerance with orally administered raffinose, lactose and L-arabinose. Clin Sci (Lond). 1990 Aug;79(2):175-83. [PubMed:2167807 ]
Osaki S, Kimura T, Sugimoto T, Hizukuri S, Iritani N: L-arabinose feeding prevents increases due to dietary sucrose in lipogenic enzymes and triacylglycerol levels in rats. J Nutr. 2001 Mar;131(3):796-9. [PubMed:11238761 ]
Seri K, Sanai K, Matsuo N, Kawakubo K, Xue C, Inoue S: L-arabinose selectively inhibits intestinal sucrase in an uncompetitive manner and suppresses glycemic response after sucrose ingestion in animals. Metabolism. 1996 Nov;45(11):1368-74. [PubMed:8931641 ]
Schutte JB, de Jong J, van Weerden EJ, Tamminga S: Nutritional implications of L-arabinose in pigs. Br J Nutr. 1992 Jul;68(1):195-207. [PubMed:1390604 ]
Shaw W, Kassen E, Chaves E: Increased urinary excretion of analogs of Krebs cycle metabolites and arabinose in two brothers with autistic features. Clin Chem. 1995 Aug;41(8 Pt 1):1094-104. [PubMed:7628083 ]
TOUSTER O, HARWELL SO: The isolation of L-arabitol from pentosuric urine. J Biol Chem. 1958 Feb;230(2):1031-41. [PubMed:13525419 ]
Ahmed Z, Shimonishi T, Bhuiyan SH, Utamura M, Takada G, Izumori K: Biochemical preparation of L-ribose and L-arabinose from ribitol: a new approach. J Biosci Bioeng. 1999;88(4):444-8. [PubMed:16232643 ]

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

L-Arabitol + NAD → L-Arabinose + NADH + Hydrogen Ion	details
L-Arabitol + NADP → L-Arabinose + NADPH + Hydrogen Ion	details

Enzyme Details

2. 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

L-Arabitol + NAD → L-Arabinose + NADH + Hydrogen Ion	details
L-Arabitol + NADP → L-Arabinose + NADPH + Hydrogen Ion	details

Showing metabocard for L-Arabinose (HMDB0000646)

MOL for HMDB0000646 (L-Arabinose)

3D MOL for HMDB0000646 (L-Arabinose)

3D SDF for HMDB0000646 (L-Arabinose)

3D-SDF for HMDB0000646 (L-Arabinose)

PDB for HMDB0000646 (L-Arabinose)

3D PDB for HMDB0000646 (L-Arabinose)

SMILES for HMDB0000646 (L-Arabinose)

INCHI for HMDB0000646 (L-Arabinose)

Structure for HMDB0000646 (L-Arabinose)

3D Structure for HMDB0000646 (L-Arabinose)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions