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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:34 UTC
Update Date2019-07-23 06:07:06 UTC
HMDB IDHMDB0030710
Secondary Accession Numbers
  • HMDB30710
Metabolite Identification
Common NameCyclomammeisin
DescriptionCyclomammeisin belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone. Thus, cyclomammeisin is considered to be a flavonoid lipid molecule. Cyclomammeisin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Cyclomammeisin has been detected, but not quantified in, fruits and mammee apples. This could make cyclomammeisin a potential biomarker for the consumption of these foods.
Structure
Data?1563862026
Synonyms
ValueSource
1,2-Dihydro-5-hydroxy-2-(1-hydroxy-1-methylethyl)-4-(3-methylbutyryl)-6-phenylfurano[2,3-H][1]benzopyran-8-oneHMDB
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-(3-methyl-1-oxobutyl)-4-phenyl-2H-furo[2,3-H]-1-benzopyran-2-one, 9ciHMDB
8,9-Dihydro-5-hydroxy-8-(1-hydroxy-1-methylethyl)-6-isovaleryl-4-phenyl-2H-furo[2,3-H]-1-benzopyran-2-one, 8ciHMDB
Mammea a/aa cyclo FHMDB
Chemical FormulaC25H26O6
Average Molecular Weight422.4703
Monoisotopic Molecular Weight422.172938564
IUPAC Name5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(3-methylbutanoyl)-4-phenyl-2H,8H,9H-furo[2,3-h]chromen-2-one
Traditional Name5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(3-methylbutanoyl)-4-phenyl-8H,9H-furo[2,3-h]chromen-2-one
CAS Registry Number30563-62-3
SMILES
CC(C)CC(=O)C1=C2OC(CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O)C(C)(C)O
InChI Identifier
InChI=1S/C25H26O6/c1-13(2)10-17(26)21-22(28)20-15(14-8-6-5-7-9-14)12-19(27)31-23(20)16-11-18(25(3,4)29)30-24(16)21/h5-9,12-13,18,28-29H,10-11H2,1-4H3
InChI KeyPTQKDRQFGLKODH-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as prenylated neoflavonoids. These are neoflavonoids that features a C5-isoprenoid substituent at any position of the A, B, or C ring. Neoflavonoids are compounds with a structure based on the 4-phenylchromene backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassNeoflavonoids
Sub ClassPrenylated neoflavonoids
Direct ParentPrenylated neoflavonoids
Alternative Parents
Substituents
  • Prenylated neoflavonoid
  • 4-phenylcoumarin
  • Angular furanocoumarin
  • Furanocoumarin
  • Butyrophenone
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Coumaran
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Vinylogous acid
  • Heteroaromatic compound
  • Tertiary alcohol
  • Lactone
  • Ketone
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point148 - 150 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0076 g/LALOGPS
logP3.99ALOGPS
logP4.5ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)8.46ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area93.06 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity126.05 m³·mol⁻¹ChemAxon
Polarizability45.33 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9205200000-5565a884c29b0c73cc3cSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0ff9-9700240000-68d1510a934ce3726959Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-1006900000-d18e88396b34de62dbc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mk-4009200000-a52086b1ff6b9f284794Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-7098000000-517f505fcd3da8551512Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0004900000-8ec39bcb342ca485a11cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-3029400000-6f5a637151e0af78b460Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-067u-6159000000-2d608648a7440b756f39Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002632
KNApSAcK IDC00010224
Chemspider ID10214256
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21592420
PDB IDNot Available
ChEBI ID546084
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Cyclomammeisin → 3,4,5-trihydroxy-6-{[8-(2-hydroxypropan-2-yl)-6-(3-methylbutanoyl)-2-oxo-4-phenyl-2H,8H,9H-furo[2,3-h]chromen-5-yl]oxy}oxane-2-carboxylic aciddetails