<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:04:53 UTC</creation_date>
  <update_date>2025-11-18 22:29:10 UTC</update_date>
  <accession>FDB001218</accession>
  <name>Arabinose</name>
  <description>Arabinose 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).</description>
  <synonyms>
    <synonym>(±)-Arabinose</synonym>
    <synonym>Aloe sugar</synonym>
    <synonym>Aloinose</synonym>
    <synonym>DL-Arabinose</synonym>
    <synonym>Pectinose</synonym>
  </synonyms>
  <chemical_formula>C5H10O5</chemical_formula>
  <average_molecular_weight>150.1299</average_molecular_weight>
  <monisotopic_moleculate_weight>150.05282343</monisotopic_moleculate_weight>
  <iupac_name>(2S,3R,4R)-2,3,4,5-tetrahydroxypentanal</iupac_name>
  <traditional_iupac>arabinose</traditional_iupac>
  <cas_registry_number>147-81-9</cas_registry_number>
  <smiles>OC[C@@H](O)[C@@H](O)[C@H](O)C=O</smiles>
  <inchi>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>
  <inchikey>PYMYPHUHKUWMLA-WDCZJNDASA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms.</description>
    <direct_parent>Pentoses</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Organic oxygen compounds</super_class>
    <class>Organooxygen compounds</class>
    <sub_class>Carbohydrates and carbohydrate conjugates</sub_class>
    <molecular_framework>Aliphatic acyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Alpha-hydroxyaldehydes</alternative_parent>
      <alternative_parent>Beta-hydroxy aldehydes</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Polyols</alternative_parent>
      <alternative_parent>Primary alcohols</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
      <alternative_parent>Short-chain aldehydes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Alcohol</substituent>
      <substituent>Aldehyde</substituent>
      <substituent>Aliphatic acyclic compound</substituent>
      <substituent>Alpha-hydroxyaldehyde</substituent>
      <substituent>Beta-hydroxy aldehyde</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Pentose monosaccharide</substituent>
      <substituent>Polyol</substituent>
      <substituent>Primary alcohol</substituent>
      <substituent>Secondary alcohol</substituent>
      <substituent>Short-chain aldehyde</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>D-arabinose</external_descriptor>
      <external_descriptor>aldehydo-arabinose</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state/>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>-2.28</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>0.40</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>3.80e+02 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>-2.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>12.33</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>(2S,3R,4R)-2,3,4,5-tetrahydroxypentanal</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>150.1299</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>150.05282343</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>OC[C@@H](O)[C@@H](O)[C@H](O)C=O</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C5H10O5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C5H10O5/c6-1-3(8)5(10)4(9)2-7/h1,3-5,7-10H,2H2/t3-,4-,5+/m1/s1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>PYMYPHUHKUWMLA-WDCZJNDASA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>97.99</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>31.38</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>13.42</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>5</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>4</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>3365</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>41654</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248528</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248529</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248530</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248531</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248532</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248533</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248534</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248535</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248536</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248537</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248538</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248539</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248540</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248541</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248542</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248543</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248544</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248545</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248546</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>248547</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26675</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26676</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>26677</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33234</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>33235</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1471160</spectrum_id>
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    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1471233</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1471282</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1471283</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1471284</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1471285</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1471286</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1471287</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1471288</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1471309</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473184</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473185</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473186</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473187</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473188</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473189</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473190</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473191</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>1473192</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB31467</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>22599</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
  </general_references>
  <foods>
    <food>
      <name>Apple</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Malus pumila</name_scientific>
      <ncbi_taxonomy_id>283210</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Arabica coffee</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Coffea arabica</name_scientific>
      <ncbi_taxonomy_id>13443</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Beer</name>
      <food_type>Type 2</food_type>
      <category>specific</category>
      <name_scientific/>
      <ncbi_taxonomy_id/>
      <average_value>0.055</average_value>
      <max_value>0.12</max_value>
      <min_value>0.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Borage</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Borago officinalis</name_scientific>
      <ncbi_taxonomy_id>13363</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Capers</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Capparis spinosa</name_scientific>
      <ncbi_taxonomy_id>65558</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Caraway</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Carum carvi</name_scientific>
      <ncbi_taxonomy_id>48032</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Carrot</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Daucus carota ssp. sativus</name_scientific>
      <ncbi_taxonomy_id>79200</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cashew nut</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Anacardium occidentale</name_scientific>
      <ncbi_taxonomy_id>171929</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cloves</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Syzygium aromaticum</name_scientific>
      <ncbi_taxonomy_id>219868</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Cocoa bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Theobroma cacao</name_scientific>
      <ncbi_taxonomy_id>3641</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Common wheat</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Triticum aestivum</name_scientific>
      <ncbi_taxonomy_id>4565</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Corn</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Zea mays</name_scientific>
      <ncbi_taxonomy_id>4577</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Dandelion</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Taraxacum officinale</name_scientific>
      <ncbi_taxonomy_id>50225</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Date</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Phoenix dactylifera</name_scientific>
      <ncbi_taxonomy_id>42345</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Fenugreek</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Trigonella foenum-graecum</name_scientific>
      <ncbi_taxonomy_id>78534</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Fig</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ficus carica</name_scientific>
      <ncbi_taxonomy_id>3494</ncbi_taxonomy_id>
    </food>
    <food>
      <name>French plantain</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Musa X paradisiaca</name_scientific>
      <ncbi_taxonomy_id>89151</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Garden onion</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Allium cepa</name_scientific>
      <ncbi_taxonomy_id>4679</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Ginkgo nuts</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Ginkgo biloba</name_scientific>
      <ncbi_taxonomy_id>3311</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Guava</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Psidium guajava</name_scientific>
      <ncbi_taxonomy_id>120290</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Okra</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Abelmoschus esculentus</name_scientific>
      <ncbi_taxonomy_id>455045</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Olive</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Olea europaea</name_scientific>
      <ncbi_taxonomy_id>4146</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Opium poppy</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Papaver somniferum</name_scientific>
      <ncbi_taxonomy_id>3469</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Potato</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Solanum tuberosum</name_scientific>
      <ncbi_taxonomy_id>4113</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Purslane</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Portulaca oleracea</name_scientific>
      <ncbi_taxonomy_id>46147</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Rice</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Oryza sativa</name_scientific>
      <ncbi_taxonomy_id>4530</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sea-buckthornberry</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Hippophae rhamnoides</name_scientific>
      <ncbi_taxonomy_id>193516</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Soft-necked garlic</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Allium sativum L. var. sativum</name_scientific>
      <ncbi_taxonomy_id>4682</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Soy bean</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Glycine max</name_scientific>
      <ncbi_taxonomy_id>3847</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Sunflower</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Helianthus annuus</name_scientific>
      <ncbi_taxonomy_id>4232</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Tamarind</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Tamarindus indica</name_scientific>
      <ncbi_taxonomy_id>58860</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Taro</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Colocasia esculenta</name_scientific>
      <ncbi_taxonomy_id>4460</ncbi_taxonomy_id>
      <average_value>588.0</average_value>
      <max_value>588.0</max_value>
      <min_value>588.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>Turmeric</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Curcuma longa</name_scientific>
      <ncbi_taxonomy_id>136217</ncbi_taxonomy_id>
      <average_value>1000.0</average_value>
      <max_value>1000.0</max_value>
      <min_value>1000.0</min_value>
      <unit>mg/100 g</unit>
    </food>
    <food>
      <name>White mustard</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Sinapis alba</name_scientific>
      <ncbi_taxonomy_id>3728</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild carrot</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Daucus carota</name_scientific>
      <ncbi_taxonomy_id>4039</ncbi_taxonomy_id>
    </food>
    <food>
      <name>Wild celery</name>
      <food_type>Type 1</food_type>
      <category>specific</category>
      <name_scientific>Apium graveolens</name_scientific>
      <ncbi_taxonomy_id>4045</ncbi_taxonomy_id>
    </food>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
