Cyclomammein (CHEM024722)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:52:55 UTC
Update Date2016-11-09 01:17:56 UTC
Accession NumberCHEM024722
Identification
Common NameCyclomammein
ClassSmall Molecule
DescriptionCyclomammein is found in fruits. Cyclomammein is found in seeds of Mammea americana (mamey) Beta-D-Glucose 6 phosphate (b-G6P) is the beta-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer. Specifically, beta-D-Glucose 6-phosphate is glucose sugar phosphorylated on carbon 6. It is a very common metabolite in cells as the vast majority of glucose entering a cell will become phosphorylated in this way. The primary reason for the immediate phosphorylation of glucose is to prevent diffusion out of the cell. The phosphorylation adds a charged phosphate group so the glucose 6-phosphate cannot easily cross the cell membrane. b-G6P is involved in the glycolysis, gluconeogenesis, pentose phosphate, and glycogen and sucrose metabolic pathways [Kegg ID: C01172]. Beta-D-Glucose 6 phosphate can be generated through beta-D-fructose phosphate or alpha-D-glucose 6 phosphate (via glucose-6-phosphate isomerase) or beta-D glucose (via hexokinase). It can then be sent off to the pentose phosphate pathway which generates the useful cofactor NADPH as well as ribulose 5-phosphate, a carbon source for the synthesis of other molecules. Alternately if the cell needs energy or carbon skeletons for synthesis then glucose 6-phosphate is targeted for glycolysis. A third route is to have glucose 6 phosphate stored or converted to glycogen, especially if blood glucose levels are high
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,3-Dihydro-4-hydroxy-2-(1-hydroxy-1-methylethyl)-5-(3-methyl-1-oxobutyl)-9-propyl-7H-furo[2,3-F][1]benzopyran-7-one, 9ciHMDB
Mammea b/ba cyclo FHMDB
Chemical FormulaC22H28O6
Average Molecular Mass388.454 g/mol
Monoisotopic Mass388.189 g/mol
CAS Registry Number30390-03-5
IUPAC Name4-hydroxy-2-(2-hydroxypropan-2-yl)-5-(3-methylbutanoyl)-9-propyl-2H,3H,7H-furo[2,3-f]chromen-7-one
Traditional Name4-hydroxy-2-(2-hydroxypropan-2-yl)-5-(3-methylbutanoyl)-9-propyl-2H,3H-furo[2,3-f]chromen-7-one
SMILESCCCC1=CC(=O)OC2=C(C(=O)CC(C)C)C(O)=C3CC(OC3=C12)C(C)(C)O
InChI IdentifierInChI=1S/C22H28O6/c1-6-7-12-9-16(24)28-21-17(12)20-13(10-15(27-20)22(4,5)26)19(25)18(21)14(23)8-11(2)3/h9,11,15,25-26H,6-8,10H2,1-5H3
InChI KeyTVYLJAPSHFFCMT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentAngular furanocoumarins
Alternative Parents
Substituents
  • Angular furanocoumarin
  • Butyrophenone
  • Benzopyran
  • 1-benzopyran
  • Coumaran
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Tertiary alcohol
  • Ketone
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
logP3.83ALOGPS
logP4.26ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)8.76ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity105.99 m³·mol⁻¹ChemAxon
Polarizability42.22 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9117000000-5d493af962d2fd183f9cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00lr-8930460000-d3147a33d266fa3da4f7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0079-0009000000-e41e8cc95a14ef361504Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-08ni-3009000000-05b5963ff0f2f1d22a3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3090000000-8128462a77a70729e3f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-bd86472b6b59efaaa5f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f79-3039000000-bf48a7c8c091389e8aa3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-5193000000-fa8b3c727ecc88503e60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-7f16ac45973a6479b3e5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-371214e0574db81e9c8cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gbl-4049000000-2dca35d98f281d3c9f3cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-9e42c3387fe4f6435022Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0009000000-f0bb3a2d86584713a762Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfs-4189000000-4d65cade4de35f951c91Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0030711
FooDB IDFDB002633
Phenol Explorer IDNot Available
KNApSAcK IDC00054441
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID35013256
ChEBI ID175940
PubChem Compound ID101967071
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.