Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-10-13 04:30:02 UTC
HMDB IDHMDB0000646
Secondary Accession Numbers
  • HMDB0000487
  • HMDB00487
  • HMDB0062088
  • HMDB00646
  • HMDB62088
Metabolite Identification
Common NameL-Arabinose
DescriptionL-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
Data?1594230226
Synonyms
ValueSource
BETA-L-ARABINOSEChEBI
WURCS=2.0/1,1,0/[a211h-1b_1-5]/1/ChEBI
b-L-ARABINOSEGenerator
Β-L-arabinoseGenerator
b-L-ArabinopyranoseHMDB
Β-L-arabinopyranoseHMDB
L-ArabinopyranoseHMDB
PectinoseHMDB
beta-L-ArabinopyranoseHMDB
ArabinopyranoseHMDB
ArabinoseHMDB
L-ArabinoseHMDB
Chemical FormulaC5H10O5
Average Molecular Weight150.1299
Monoisotopic Molecular Weight150.05282343
IUPAC Name(2S,3R,4S,5S)-oxane-2,3,4,5-tetrol
Traditional Nameβ-L-arabinopyranose
CAS Registry Number7296-56-2
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 KeySRBFZHDQGSBBOR-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentoses
Alternative Parents
Substituents
  • Pentose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point158 - 160 °CNot Available
Boiling Point415.00 to 416.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility500 mg/mLNot Available
LogP-3.02HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1220 g/LALOGPS
logP-2.6ALOGPS
logP-2.3ChemAxon
logS0.91ALOGPS
pKa (Strongest Acidic)11.31ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area90.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity29.96 m³·mol⁻¹ChemAxon
Polarizability13.37 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+135.36730932474
DeepCCS[M-H]-133.16330932474
DeepCCS[M-2H]-167.90530932474
DeepCCS[M+Na]+141.98230932474
AllCCS[M+H]+134.232859911
AllCCS[M+H-H2O]+129.632859911
AllCCS[M+NH4]+138.432859911
AllCCS[M+Na]+139.732859911
AllCCS[M-H]-124.832859911
AllCCS[M+Na-2H]-126.532859911
AllCCS[M+HCOO]-128.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-ArabinoseO[C@H]1CO[C@H](O)[C@H](O)[C@H]1O3000.0Standard polar33892256
L-ArabinoseO[C@H]1CO[C@H](O)[C@H](O)[C@H]1O1530.6Standard non polar33892256
L-ArabinoseO[C@H]1CO[C@H](O)[C@H](O)[C@H]1O1384.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-Arabinose,1TMS,isomer #1C[Si](C)(C)O[C@H]1CO[C@H](O)[C@H](O)[C@H]1O1494.4Semi standard non polar33892256
L-Arabinose,1TMS,isomer #2C[Si](C)(C)O[C@H]1OC[C@H](O)[C@H](O)[C@H]1O1456.1Semi standard non polar33892256
L-Arabinose,1TMS,isomer #3C[Si](C)(C)O[C@H]1[C@@H](O)OC[C@H](O)[C@@H]1O1492.8Semi standard non polar33892256
L-Arabinose,1TMS,isomer #4C[Si](C)(C)O[C@H]1[C@@H](O)CO[C@H](O)[C@@H]1O1501.0Semi standard non polar33892256
L-Arabinose,2TMS,isomer #1C[Si](C)(C)O[C@H]1CO[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O1519.1Semi standard non polar33892256
L-Arabinose,2TMS,isomer #2C[Si](C)(C)O[C@H]1CO[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O1515.9Semi standard non polar33892256
L-Arabinose,2TMS,isomer #3C[Si](C)(C)O[C@H]1CO[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C1471.6Semi standard non polar33892256
L-Arabinose,2TMS,isomer #4C[Si](C)(C)O[C@H]1[C@@H](O)CO[C@H](O[Si](C)(C)C)[C@@H]1O1518.4Semi standard non polar33892256
L-Arabinose,2TMS,isomer #5C[Si](C)(C)O[C@H]1OC[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C1477.7Semi standard non polar33892256
L-Arabinose,2TMS,isomer #6C[Si](C)(C)O[C@H]1[C@@H](O)CO[C@H](O)[C@@H]1O[Si](C)(C)C1495.9Semi standard non polar33892256
L-Arabinose,3TMS,isomer #1C[Si](C)(C)O[C@H]1CO[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O1548.5Semi standard non polar33892256
L-Arabinose,3TMS,isomer #2C[Si](C)(C)O[C@H]1CO[C@H](O[Si](C)(C)C)[C@H](O)[C@H]1O[Si](C)(C)C1560.9Semi standard non polar33892256
L-Arabinose,3TMS,isomer #3C[Si](C)(C)O[C@H]1CO[C@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C1553.8Semi standard non polar33892256
L-Arabinose,3TMS,isomer #4C[Si](C)(C)O[C@H]1[C@@H](O)CO[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C1576.0Semi standard non polar33892256
L-Arabinose,4TMS,isomer #1C[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)C1645.4Semi standard non polar33892256
L-Arabinose,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CO[C@H](O)[C@H](O)[C@H]1O1744.5Semi standard non polar33892256
L-Arabinose,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1OC[C@H](O)[C@H](O)[C@H]1O1707.1Semi standard non polar33892256
L-Arabinose,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)OC[C@H](O)[C@@H]1O1726.7Semi standard non polar33892256
L-Arabinose,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@H]1[C@@H](O)CO[C@H](O)[C@@H]1O1732.8Semi standard non polar33892256
L-Arabinose,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1CO[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O)[C@H]1O1990.7Semi standard non polar33892256
L-Arabinose,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1CO[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O1979.0Semi standard non polar33892256
L-Arabinose,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1CO[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C1956.2Semi standard non polar33892256
L-Arabinose,2TBDMS,isomer #4CC(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]1O1976.0Semi standard non polar33892256
L-Arabinose,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)O[C@H]1OC[C@H](O)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C1949.6Semi standard non polar33892256
L-Arabinose,2TBDMS,isomer #6CC(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)C1958.4Semi standard non polar33892256
L-Arabinose,3TBDMS,isomer #1CC(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]1O2238.9Semi standard non polar33892256
L-Arabinose,3TBDMS,isomer #2CC(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)C2254.8Semi standard non polar33892256
L-Arabinose,3TBDMS,isomer #3CC(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)C2250.2Semi standard non polar33892256
L-Arabinose,3TBDMS,isomer #4CC(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)C2239.3Semi standard non polar33892256
L-Arabinose,4TBDMS,isomer #1CC(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)C2479.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (Non-derivatized) - 70eV, Positivesplash10-000x-9400000000-f20d1c35a7eeea1609a52017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_3_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_3_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TMS_4_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-Arabinose GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Arabinose 10V, Positive-QTOFsplash10-0ue9-0900000000-4856e933b915ddbb05542017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Arabinose 20V, Positive-QTOFsplash10-0f89-0900000000-79e8278d7ae6b34a77722017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Arabinose 40V, Positive-QTOFsplash10-08os-9100000000-64c106194d5825a11d362017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Arabinose 10V, Negative-QTOFsplash10-0002-1900000000-988a7d2dad8bc555d5022017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Arabinose 20V, Negative-QTOFsplash10-000t-2900000000-31127350481e63c82ff72017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Arabinose 40V, Negative-QTOFsplash10-0006-9000000000-264c06bc93b8e518bbfb2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Arabinose 10V, Negative-QTOFsplash10-0002-7900000000-524214992b29f1ff9b802021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Arabinose 20V, Negative-QTOFsplash10-0a4i-9000000000-f758a7d33dac04b062752021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Arabinose 40V, Negative-QTOFsplash10-0a4l-9000000000-4b3e154b12c2ee07bf582021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Arabinose 10V, Positive-QTOFsplash10-0gc0-1900000000-e784a3fdca89dcb59c122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Arabinose 20V, Positive-QTOFsplash10-0m4p-9100000000-fc295e2732f55a0a18c12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-Arabinose 40V, Positive-QTOFsplash10-0007-9000000000-ba5f29c2c79df8d0956f2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2020-07-08Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2020-07-08Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified2.5 (0.0-5.0) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified19.5 (8.0-38.0) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified8.8 (8.0-31.0) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not Specified
Normal
details
UrineDetected and Quantified8.8 (0.8-19.4) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified8.75 (6.12-11.84) umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified27.483 +/- 18.288 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified13.3 (1.3-22.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified3.0 (0.0-7.0) uMAdult (>18 years old)BothRibose-5-phosphate isomerase deficiency details
Cerebrospinal Fluid (CSF)Detected and Quantified92.0 (66.0-135.0) uMChildren (1-13 years old)BothRibose-5-phosphate isomerase deficiency details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified17.07 +/- 14.128 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified38.0 (37.0-41.0) umol/mmol creatinineAdult (>18 years old)BothRibose-5-phosphate isomerase deficiency details
Associated Disorders and Diseases
Disease References
Ribose-5-phosphate isomerase deficiency
  1. 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
  1. 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
  1. 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)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012306
KNApSAcK IDC00001113
Chemspider ID388821
KEGG Compound IDC02479
BioCyc IDBETA-L-ARABINOSE
BiGG IDNot Available
Wikipedia LinkArabinose
METLIN IDNot Available
PubChem Compound439764
PDB IDNot Available
ChEBI ID40886
Food Biomarker OntologyNot Available
VMH IDARAB_L
MarkerDB IDMDB00000207
Good Scents IDrw1006871
References
Synthesis ReferenceWhistler, 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)Download (PDF)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. TOUSTER O, HARWELL SO: The isolation of L-arabitol from pentosuric urine. J Biol Chem. 1958 Feb;230(2):1031-41. [PubMed:13525419 ]
  9. 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

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 Iondetails
L-Arabitol + NADP → L-Arabinose + NADPH + Hydrogen Iondetails
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 Iondetails
L-Arabitol + NADP → L-Arabinose + NADPH + Hydrogen Iondetails