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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-15 09:55:03 UTC
Update Date2018-05-19 21:50:00 UTC
HMDB IDHMDB0010207
Secondary Accession Numbers
  • HMDB10207
Metabolite Identification
Common NameL-Rhamnulose
DescriptionL-Rhamnulose is a breakdown product of L-rhamnose, which is ubiquitous and particularly abundant in some plants, such as buckthorn. Rhamnose is also one of the sugars regularly used to conduct the dual sugar permeability test. Rhamnose is fermented by some colonic bacteria into L-rhamnulose. Three bacterial (gut micrflora) enzymes are involved in Rhamnose degradation including rhaB (rhamulose kinase), rhaA (rhamnose isomerase), and rhaD (rhamnulose-1-phosphate aldolase). L-rhamnulose kinase catalyzes the transfer of the gamma-phosphate group from ATP to the 1-hydroxyl group of L-rhamnulose.
Structure
Thumb
Synonyms
ValueSource
6-Deoxy-L-mannoseHMDB
6-Deoxy-L-sorboseHMDB
6-Deoxy-L-xylo-hex-2-uloseHMDB
L-MannomethyloseHMDB
L-RhamnoseHMDB
RhamnuloseHMDB
Chemical FormulaC6H12O5
Average Molecular Weight164.1565
Monoisotopic Molecular Weight164.068473494
IUPAC Name(3S,4R,5S)-1,3,4,5-tetrahydroxyhexan-2-one
Traditional NameL-rhamnulose
CAS Registry Number87-96-7
SMILES
C[C@H](O)[C@@H](O)[C@H](O)C(=O)CO
InChI Identifier
InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h3,5-8,10-11H,2H2,1H3/t3-,5+,6+/m0/s1
InChI KeyQZNPNKJXABGCRC-OTWZMJIISA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentFatty alcohols
Alternative Parents
Substituents
  • Fatty alcohol
  • Acyloin
  • Beta-hydroxy ketone
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Ketone
  • Secondary alcohol
  • Polyol
  • Primary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility388 g/LALOGPS
logP-1.8ALOGPS
logP-2.2ChemAxon
logS0.37ALOGPS
pKa (Strongest Acidic)10.47ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity36.02 m³·mol⁻¹ChemAxon
Polarizability15.42 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9100000000-ad22e0100103a9ec21f4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0550-7739500000-fc1eb1160f642aa0004eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-2900000000-4fea56d8ac6e1f9c39f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9200000000-1970754062af802fdcc1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-c31c6727c566e780cfc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0k9i-9600000000-e099358e8071a9159c2fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abi-9200000000-df6af27b57ded6f02536View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-70d5c6dd38db6d9ac9abView in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000437 +/- 0.000028 uMAdult (>18 years old)Not Specified
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB027362
KNApSAcK IDNot Available
Chemspider ID388459
KEGG Compound IDC00861
BioCyc IDRHAMNULOSE-1P
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439330
PDB IDNot Available
ChEBI ID17897
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Petrich K, Ludwig P, Kuhn H, Schewe T: The suppression of 5-lipoxygenation of arachidonic acid in human polymorphonuclear leucocytes by the 15-lipoxygenase product (15S)-hydroxy-(5Z,8Z,11Z,13E)-eicosatetraenoic acid: structure-activity relationship and mechanism of action. Biochem J. 1996 Mar 15;314 ( Pt 3):911-6. [PubMed:8615788 ]
  2. Haviv F, Ratajczyk JD, DeNet RW, Martin YC, Dyer RD, Carter GW: Structural requirements for the inhibition of 5-lipoxygenase by 15-hydroxyeicosa-5,8,11,13-tetraenoic acid analogues. J Med Chem. 1987 Feb;30(2):254-63. [PubMed:3806609 ]