Showing Compound Card for D-manno-2-Heptulose (CDB000137)

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Record Information
Version1.0
Created at2020-03-18 23:26:09 UTC
Updated at2020-11-18 16:34:50 UTC
CannabisDB IDCDB000137
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameD-manno-2-Heptulose
Description1,3,4,5,6,7-Hexahydroxyheptan-2-one, D-manno-2-Heptulose or mannoheptulose belongs to the class of organic compounds known as heptoses. Heptoses are monosaccharides with seven carbon atoms in their structure. D-manno-2-heptulose is one of the few naturally occurring heptoses found primarily in alfalfa, avocados, and primrose (PMID: 31293606 ). D-manno-2-heptulose is also found in cannabis plants (PMID: 6991645 ). Though the carbohydrate is thought to be produced during photosynthesis, the precise biological pathway for the synthesis of mannoheptulose is still unknown. Like other sugars, it is transported in the plant through the phloem. Because it inhibits glycolysis in vitro, it has been investigated as a novel nutraceutical for weight management in dogs. However, while it is suggested that mannoheptulose affects the energy balance of adult dogs, research is still inconclusive regarding the significance of the alteration of energy expenditure in dogs (PMID: 26479244 , PMID: 26656105 , PMID: 28444793 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC7H14O7
Average Molecular Weight210.18
Monoisotopic Molecular Weight210.074
IUPAC Name(3R,4R,5R,6S)-1,3,4,5,6,7-hexahydroxyheptan-2-one
Traditional Name(3R,4R,5R,6S)-1,3,4,5,6,7-hexahydroxyheptan-2-one
CAS Registry NumberNot Available
SMILES
OC[C@H](O)[C@@H](O)[C@@H](O)[C@@H](O)C(=O)CO
InChI Identifier
InChI=1S/C7H14O7/c8-1-3(10)5(12)7(14)6(13)4(11)2-9/h3,5-10,12-14H,1-2H2/t3-,5+,6-,7+/m0/s1
InChI KeyHSNZZMHEPUFJNZ-HTPUFBNKSA-N
Chemical Taxonomy
ClassificationNot classified
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-2.4ALOGPS
logP-3.9ChemAxon
logS0.03ALOGPS
pKa (Strongest Acidic)8.91ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area138.45 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity43.52 m³·mol⁻¹ChemAxon
Polarizability18.99 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View 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 IDNot Available
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 LinkNot Available
METLIN IDNot Available
PubChem Compound25791640
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Pedreschi R, Uarrota V, Fuentealba C, Alvaro JE, Olmedo P, Defilippi BG, Meneses C, Campos-Vargas R: Primary Metabolism in Avocado Fruit. Front Plant Sci. 2019 Jun 26;10:795. doi: 10.3389/fpls.2019.00795. eCollection 2019. [PubMed:31293606 ]
  2. McKnight LL, Eyre R, Gooding MA, Davenport GM, Shoveller AK: Dietary Mannoheptulose Increases Fasting Serum Glucagon Like Peptide-1 and Post-Prandial Serum Ghrelin Concentrations in Adult Beagle Dogs. Animals (Basel). 2015 Jun 16;5(2):442-54. doi: 10.3390/ani5020365. [PubMed:26479244 ]
  3. McKnight LL, Root-McCaig J, Wright D, Davenport GM, France J, Shoveller AK: Dietary Mannoheptulose Does Not Significantly Alter Daily Energy Expenditure in Adult Labrador Retrievers. PLoS One. 2015 Dec 11;10(12):e0143324. doi: 10.1371/journal.pone.0143324. eCollection 2015. [PubMed:26656105 ]
  4. McKnight LL, France J, Wright D, Davenport G, Shoveller AK: Dietary mannoheptulose does not alter glucose or lipid metabolism in adult Labrador Retrievers. J Anim Physiol Anim Nutr (Berl). 2018 Feb;102(1):e122-e131. doi: 10.1111/jpn.12713. Epub 2017 Apr 26. [PubMed:28444793 ]
  5. 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 ]