Showing Compound Card for L-Arabinose (CDB000071)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:23:42 UTC
Updated at2020-11-18 16:34:43 UTC
CannabisDB IDCDB000071
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameL-Arabinose
DescriptionArabinose or L-arabinose is an aldopentose, a monosaccharide with an aldehyde functional group. Although most saccharides have the D-form, arabinose is most abundant in the L-form. It is colorless with a prism or needle like crystal that is very soluble in water. It has a sweet taste. It is one of the most abundant components released after complete hydrolysis of non-starch polysaccharides (NSP) from vegetables. However, NSPs which include cellulose, hemi-cellulose, pectin, and oligosaccharides, are complicated compounds both in physical structure and chemical composition. The NSPs are resistant to the digestive enzymes and pass to the hindgut where microbial degradation takes place. When L-arabinose is ingested, it is absorbed from the intestinal tract at a lower rate than glucose with a portion excreted in the urine. Although widely present in nature, L-arabinose is rarely used, and its physiological effects in vivo have received little attention. L-arabinose selectively inhibits intestinal sucrase activity in a non-competitive manner and suppresses the plasma glucose increase after sucrose ingestion (PMID: 8931641 ). Because the intestinal absorption of sucrose is inhibited in the presence of L-arabinose, the absorption of sucrose should be reduced by arabinose ingestion. Most of the studies reported so far on the absorption and utilization of L-arabinose have been with non human omnivore animal (PMID:11238761 ; PMID: 1390604 ).. In a rare published case, two autistic brothers, with no known metabolic disease, had nearly six times greater L-arabinose(179 µmol/mmol creatinine) in their urine compared to normal children (PMID: 7628083 ). L-Arabinose was elevated in the CSF and urine of patients with ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism (PMID: 14988808 ). L-Arabinose is also a microbial metabolite found in Mycobacterium (PMID: 16232643 ). Arabinose is a major monosaccharide sugar found in cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S,3R,4R)-2,3,4,5-TetrahydroxypentanalChEBI
(+/-)-arabinoseHMDB
Aloe sugarHMDB
AloinoseHMDB
DL-ArabinoseHMDB
PectinoseHMDB
D-ArabinoseChEBI
Chemical FormulaC5H10O5
Average Molecular Weight150.13
Monoisotopic Molecular Weight150.0528
IUPAC Name(2S,3R,4R)-2,3,4,5-tetrahydroxypentanal
Traditional Namearabinose
CAS Registry Number147-81-9
SMILES
OC[C@@H](O)[C@@H](O)[C@H](O)C=O
InChI Identifier
InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4-,5+/m1/s1
InChI KeyPYMYPHUHKUWMLA-WDCZJNDASA-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
  • Beta-hydroxy aldehyde
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Short-chain aldehyde
  • Primary alcohol
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point164 - 165 °CWikipedia
Boiling PointNot AvailableNot Available
Water Solubility834 g/L at 25 °CWikipedia
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.3ALOGPS
logP-2.9ChemAxon
logS0.4ALOGPS
pKa (Strongest Acidic)12.33ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity31.38 m³·mol⁻¹ChemAxon
Polarizability13.42 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSL-Arabinose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-052f-9100000000-3d844ea1b588172feaf0Spectrum
Predicted GC-MSL-Arabinose, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05i0-6249400000-6324b88618b9174f1ee5Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-08mi-9100000000-fdc6cb3672d0fd9782e42020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-0a4i-9000000000-8b4cbdfdbd1d64750afc2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 1V, negativesplash10-0002-1900000000-a6fad2b086e4d72e64552020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 4V, negativesplash10-000j-9500000000-7f3c671f5a2325c135212020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 8V, negativesplash10-052r-9000000000-4607894e05698b4efd4b2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 10V, negativesplash10-0a4r-9000000000-7713ba3bfd41873ed05b2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 14V, negativesplash10-0a4i-9000000000-19cc19a6070f8904f2232020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 17V, negativesplash10-0a4i-9000000000-cbfe90fac8fd1f09d1782020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 20V, negativesplash10-0a4i-9000000000-194cea61e7f4bb1161082020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 10V, negativesplash10-001i-2900000000-0431fbb715edbb5c28542020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-001i-0900000000-9b7382416823533b7db12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-001i-0900000000-b354fa776d3c927b52a82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, negativesplash10-001i-1900000000-4f54308f655454dcf2382020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-001i-2900000000-ffb4e5e554a72f34fd7b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, negativesplash10-001i-4900000000-df24839373685cc979762020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-001r-7900000000-08514302c6b21ad9497c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, negativesplash10-008i-9700000000-9b73d2467b158cb7fe642020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-00dr-9300000000-80b57725a8299b2e9afa2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-00dr-9100000000-f5eb0b039697ddead9f82020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-2900000000-f8b9c6d77ac7485b2a132015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9300000000-c381cba09705c9d223672015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08fv-9000000000-157eda9875c5cd43b3322015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000j-9400000000-8bb17d4c0bc5362b26102015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06ri-9200000000-f20b8cc45d01968599912015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-83841c4e2cbd5aa6df092015-09-15View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Sucrase-isomaltase, intestinalSIP14410 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Taste receptor type 1 member 3TAS1R31p36.33Q7RTX0 details
Taste receptor type 1 member 2TAS1R21p36.13Q8TE23 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0029942
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001219
KNApSAcK IDNot Available
Chemspider ID59687
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkArabinose
METLIN IDNot Available
PubChem Compound66308
PDB IDNot Available
ChEBI ID46983
References
General References
  1. 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. doi: 10.1016/s0026-0495(96)90117-1. [PubMed:8931641 ]
  2. 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. doi: 10.1093/jn/131.3.796. [PubMed:11238761 ]
  3. 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. doi: 10.1079/bjn19920077. [PubMed:1390604 ]
  4. 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 ]
  5. 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. doi: 10.1016/s1389-1723(99)80225-4. [PubMed:16232643 ]
  6. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  7. 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. doi: 10.1086/383204. Epub 2004 Feb 25. [PubMed:14988808 ]

Enzymes

Enzyme Details
1. Sucrase-isomaltase, intestinal
General function:
Involved in catalytic activity
Specific function:
Plays an important role in the final stage of carbohydrate digestion. Isomaltase activity is specific for both alpha-1,4- and alpha-1,6-oligosaccharides.
Gene Name:
SI
Uniprot ID:
P14410
Molecular weight:
Not Available