Showing Compound Card for Raffinose (CDB000051)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:22:58 UTC
Updated at2020-11-18 16:34:42 UTC
CannabisDB IDCDB000051
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameRaffinose
DescriptionRaffinose is a trisaccharide containing glucose, galactose, and fructose units. It belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. Raffinose is an extremely weak basic (essentially neutral) compound (based on its pKa). Raffinose exists as a white crystalline powder and has a sweet taste approximately 10% that of sucrose. The raffinose family of oligosaccharides (RFOs) are alpha-galactosyl derivatives of sucrose, and the most common are the trisaccharide raffinose, the tetrasaccharide stachyose, and the pentasaccharide verbascose. RFOs are almost ubiquitous in the plant kingdom, being found in a large variety of seeds from many different families, and they rank second only to sucrose in abundance as soluble carbohydrates. Raffinose (and other RFOs) is non-digestible in humans and other monogastric animals (pigs and poultry) who do not possess the α-GAL (alpha-galactosidase) enzyme to break down raffinose. In the lower intestine of most mammals, raffinose is fermented by gas-producing bacteria that possess the α-GAL enzyme and make short-chain fatty acids (SCFA) (acetic, propionic, butyric acids) as well as the flatulence commonly associated with eating beans and other vegetables. Raffinose can be found in beans, cabbage, brussels sprouts, broccoli, asparagus, other vegetables, and whole grains. In humans, raffinose is involved in galactose metabolism. Raffinose is one of at least 5 oligosaccharides that are found in cannabis plants (PMID: 6991645 ). Raffinose is used in skin moisturizers and smoothers, prebiotics (it allegedly promotes growth of lactobacilli and bifidobacteria), and as a food or drink additive. Either raffinose or sucrose can be used as a base substance for sucralose.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
6g-alpha-D-GalactosylsucroseChEBI
alpha-D-Galactopyranosyl-(1->6)-alpha-D-glucopyranosyl beta-D-fructofuranosideChEBI
alpha-D-Galp-(1->6)-alpha-D-GLCP-(12)-beta-D-frufChEBI
GossyposeChEBI
MelitoseChEBI
MelitrioseChEBI
RafinoseChEBI
RaflinoseChEBI
6g-a-D-GalactosylsucroseGenerator
6g-Α-D-galactosylsucroseGenerator
a-D-Galactopyranosyl-(1->6)-a-D-glucopyranosyl b-D-fructofuranosideGenerator
Α-D-galactopyranosyl-(1->6)-α-D-glucopyranosyl β-D-fructofuranosideGenerator
a-D-Galp-(1->6)-a-D-GLCP-(12)-b-D-frufGenerator
Α-D-galp-(1->6)-α-D-GLCP-(12)-β-D-frufGenerator
D-(+)-RaffinoseHMDB
D-RaffinoseHMDB
beta-D-Fructofuranosyl O-alpha-D-galactopyranosyl-(1→6)-alpha-D-glucopyranosideHMDB
Β-D-fructofuranosyl O-α-D-galactopyranosyl-(1→6)-α-D-glucopyranosideHMDB
RaffinoseHMDB
Chemical FormulaC18H32O16
Average Molecular Weight504.44
Monoisotopic Molecular Weight504.169
IUPAC Name(2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol
Traditional Nameraffinose
CAS Registry Number512-69-6
SMILES
OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C18H32O16/c19-1-5-8(22)11(25)13(27)16(31-5)30-3-7-9(23)12(26)14(28)17(32-7)34-18(4-21)15(29)10(24)6(2-20)33-18/h5-17,19-29H,1-4H2/t5-,6-,7-,8+,9-,10-,11+,12+,13-,14-,15+,16+,17-,18+/m1/s1
InChI KeyMUPFEKGTMRGPLJ-ZQSKZDJDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentOligosaccharides
Alternative Parents
Substituents
  • Oligosaccharide
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Oxane
  • Tetrahydrofuran
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Alcohol
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point80 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility203 mg/mLNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-3.4ALOGPS
logP-6.3ChemAxon
logS0.12ALOGPS
pKa (Strongest Acidic)11.7ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area268.68 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity101.19 m³·mol⁻¹ChemAxon
Polarizability46.17 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSRaffinose, non-derivatized, GC-MS Spectrumsplash10-0i00-0984100000-9982c277f436fd7788a5Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, positivesplash10-0a4o-0909000000-8e525d469d91c8d958cb2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-004l-0229100000-0e86b420bc16a12fcb5a2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 20V, positivesplash10-06vi-1529000000-ca7b5ce31b75cedc69b32020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 40V, positivesplash10-0076-9430100000-a53bd43a032e7db1cb4d2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT 40V, negativesplash10-00fr-0986000000-0bdcdaf84ed0bc9327952020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, negativesplash10-0uk9-7930060000-ac8500ed18415634b6662020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0kp0-9820010000-016241d403acb7b8c4912020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-004i-0090000000-b2481c83084387e128382020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 12V, negativesplash10-0udi-0100090000-6da14a924bf87e052d402020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 19V, negativesplash10-0fb9-2910030000-27a02c65bb1897d0b2342020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 25V, negativesplash10-002r-6910000000-a9a928caa280abfbd94d2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 30V, negativesplash10-000i-9710000000-49017cc7d06a2393eab32020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 20V, negativesplash10-0udi-0000090000-2f07c4e073c08b44cbc62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 22V, negativesplash10-0udi-0200090000-48ca69a647f8a160cfcf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 25V, negativesplash10-0udi-2611090000-02d0b16ed861ce2e22512020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 30V, negativesplash10-0ug0-4910020000-75edd90b36765151b9232020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 37V, negativesplash10-0079-9820000000-163d92c370b7f8085dc92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 45V, negativesplash10-0kmr-9510000000-b6c552ccce26ade9d72c2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 55V, negativesplash10-05g0-9300000000-7eeb9c4ff5f74d594a402020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0901000000-0da93ae66a255c5396132016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03gi-0905000000-b14ef3fbf37ecca83a6b2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9800000000-07dcde9d0cb5481f432b2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2901000000-f86191b929c7806ddd562016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03fr-0900000000-e4a2b4341d424cbea7d02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002e-6910000000-5d77ce1936f86d2012fe2016-08-03View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Alpha-galactosidase AGLAP06280 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Alpha-galactosidase AGLAP06280 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0003213
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001145
Chemspider ID388379
KEGG Compound IDC00492
BioCyc IDCPD-1099
BiGG IDNot Available
Wikipedia LinkRaffinose
METLIN IDNot Available
PubChem Compound439242
PDB IDNot Available
ChEBI ID16634
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 ]

Enzymes

Enzyme Details
1. Alpha-galactosidase A
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GLA
Uniprot ID:
P06280
Molecular weight:
Not Available