Showing Compound Card for Aldehydo-L-rhamnose (CDB000139)

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Record Information
Version1.0
Created at2020-03-18 23:26:14 UTC
Updated at2020-11-18 16:34:50 UTC
CannabisDB IDCDB000139
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameAldehydo-L-rhamnose
DescriptionAldehydo-L-rhamnose belongs to the class of organic compounds known as hexoses. It is the open chain aldehyde form of D-rhamnose. Hexoses are monosaccharides in which the sugar unit is a six-carbon containing moiety. It can be classified as either a methyl-pentose or a 6-deoxy-hexose. Aldehydo-L-rhamnose is a neutral compound. It is an odorless white powder with a sweet taste ( Ref:DOI ). Rhamnose (Rha, Rham) is a naturally occurring L-form deoxy sugar. This is unusual, since most of the naturally occurring sugars are in D-form. It is found in banana, guava, plum, onion, okra, olive and garlic bulb; in caraway, sunflower, flax and coconut seeds; in coffee beans and in fig and tarragon leaves ( Ref:DOI ). Rhamnose is methyl-pentose also found in Cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R,3R,4S,5S)-2,3,4,5-TetrahydroxyhexanalChEBI
L-RhaChEBI
L-RhamnoseChEBI
DeoxymannoseMeSH
RhamnoseMeSH
Rhamnose, L isomerMeSH
Rhamnose, L-isomerMeSH
Chemical FormulaC6H12O5
Average Molecular Weight164.16
Monoisotopic Molecular Weight164.0685
IUPAC Name(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal
Traditional Name6-deoxy-L-mannose
CAS Registry Number4469-18-5
SMILES
C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O
InChI Identifier
InChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4-,5-,6-/m0/s1
InChI KeyPNNNRSAQSRJVSB-BXKVDMCESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Medium-chain aldehyde
  • Beta-hydroxy aldehyde
  • Alpha-hydroxyaldehyde
  • Secondary alcohol
  • Polyol
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2ALOGPS
logP-2.5ChemAxon
logS0.2ALOGPS
pKa (Strongest Acidic)12.31ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.8 m³·mol⁻¹ChemAxon
Polarizability15.24 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSAldehydo-L-rhamnose, 1 MEOX; 4 TMS, GC-MS Spectrumsplash10-014i-0920000000-3f32654cd6b207d5192cSpectrum
GC-MSAldehydo-L-rhamnose, 1 MEOX; 4 TMS, GC-MS Spectrumsplash10-014i-0910000000-3efed9ba21b4acc1a0a7Spectrum
GC-MSAldehydo-L-rhamnose, non-derivatized, GC-MS Spectrumsplash10-014i-0920000000-15cadd38d19e98599380Spectrum
GC-MSAldehydo-L-rhamnose, non-derivatized, GC-MS Spectrumsplash10-014i-0920000000-845777ce5ccb02564dd4Spectrum
GC-MSAldehydo-L-rhamnose, non-derivatized, GC-MS Spectrumsplash10-014i-0910000000-a3998948f1f154365feaSpectrum
GC-MSAldehydo-L-rhamnose, non-derivatized, GC-MS Spectrumsplash10-014i-0900000000-09ff33efc7ead61776acSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-c17a9df600308d9b31be2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, negativesplash10-0a4i-9300000000-aba9c0e75315919d15ca2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 2V, negativesplash10-03di-0900000000-5bc4a1e81d1743e4d8882020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 6V, negativesplash10-114r-4900000000-cce3aaf678cc70d6861a2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 8V, negativesplash10-0pb9-9700000000-4f6230f5365dba6dd52f2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 12V, negativesplash10-0a4i-9100000000-9477982822aed35186822020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 16V, negativesplash10-0a4i-9000000000-594366ab16c0cac996712020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 20V, negativesplash10-0a4i-9000000000-f0b38b5601df3611821c2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0udi-3900000000-a5276b0d1c6f7703894f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-004i-2900000000-2a20cb5f730a3fd744482020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0089-9000000000-643fd0369e6935a5767c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 11V, negativesplash10-0532-9400000000-2e4332a61dcaf8add5aa2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-3900000000-ff3539fb021325c23c4a2015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9200000000-b270b5d83d44008211ba2015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-f516852459b277fdb1572015-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ly9-9600000000-efc90d58c6475abfcecd2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0abi-9100000000-3b89500afd7b488df6fa2015-09-15View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-7b10fe17f3ce9401fd3f2015-09-15View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDDB02961
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRhamnose
METLIN IDNot Available
PubChem Compound19233
PDB IDNot Available
ChEBI ID16055
References
General References
  1. 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 ]