Showing Compound Card for d-manno-heptulose (CDB000239)

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Record Information
Version1.0
Created at2020-03-19 00:26:19 UTC
Updated at2020-12-07 19:07:18 UTC
CannabisDB IDCDB000239
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Named-manno-heptulose
DescriptionD-Manno-Heptulose, D-manno-2-Heptulose 1,3,4,5,6,7-Hexahydroxyheptan-2-one 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. It has been found primarily in alfalfa, avocados, primrose (PMID: 31293606 ) and also in cannabis (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 of its in vitro inhibition of glycolysis, 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 (PMID: 26479244 , PMID: 26656105 , PMID: 28444793 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
alpha-D-MannoheptulopyranoseChEBI
MannoheptuloseKegg
a-D-MannoheptulopyranoseGenerator
Α-D-mannoheptulopyranoseGenerator
a-D-Manno-heptulopyranoseHMDB
Α-D-manno-heptulopyranoseHMDB
MannoketoheptoseHMDB
(+)-MannoheptuloseHMDB
D-MannoheptuloseHMDB
D-Manno-heptuloseHMDB
alpha-D-Manno-2-heptulopyranoseHMDB
Α-D-manno-2-heptulopyranoseHMDB
Chemical FormulaC7H14O7
Average Molecular Weight210.18
Monoisotopic Molecular Weight210.074
IUPAC Name(2S,3S,4S,5S,6R)-2,6-bis(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional Namemannoketoheptose
CAS Registry Number60426-75-7
SMILES
OC[C@H]1O[C@@](O)(CO)[C@@H](O)[C@@H](O)[C@@H]1O
InChI Identifier
InChI=1S/C7H14O7/c8-1-3-4(10)5(11)6(12)7(13,2-9)14-3/h3-6,8-13H,1-2H2/t3-,4-,5+,6+,7+/m1/s1
InChI KeyHAIWUXASLYEWLM-VEIUFWFVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentC-glycosyl compounds
Alternative Parents
Substituents
  • Hexose monosaccharide
  • C-glycosyl compound
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point151 - 152 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.6ALOGPS
logP-3.4ChemAxon
logS0.64ALOGPS
pKa (Strongest Acidic)10.28ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area130.61 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity42.32 m³·mol⁻¹ChemAxon
Polarizability19.14 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSd-manno-heptulose, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSd-manno-heptulose, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
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
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2290000000-b75209a2ded2569fd90d2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9110000000-469f32ec283b1ab3663a2021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-e748c71d0610471789b62021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0490000000-2c85b0b40e4eb7c699e12021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9330000000-154c47472db8afc2b7be2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0c29-9000000000-947d80d103b7151973d42021-09-25View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0029935
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001201
KNApSAcK IDC00052342
Chemspider ID390153
KEGG Compound IDC08236
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound441419
PDB IDNot Available
ChEBI ID28657
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 ]