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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:34 UTC
Update Date2022-03-07 02:52:39 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. Cyclomammeisin has been detected, but not quantified in, fruits and mammee apples (Mammea americana). This could make cyclomammeisin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cyclomammeisin.
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point148 - 150 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.19 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+198.2231661259
DarkChem[M-H]-199.40331661259
DeepCCS[M+H]+211.93830932474
DeepCCS[M-H]-209.54330932474
DeepCCS[M-2H]-242.42630932474
DeepCCS[M+Na]+217.85130932474
AllCCS[M+H]+200.832859911
AllCCS[M+H-H2O]+198.332859911
AllCCS[M+NH4]+203.132859911
AllCCS[M+Na]+203.832859911
AllCCS[M-H]-207.232859911
AllCCS[M+Na-2H]-207.432859911
AllCCS[M+HCOO]-207.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CyclomammeisinCC(C)CC(=O)C1=C2OC(CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O)C(C)(C)O4385.5Standard polar33892256
CyclomammeisinCC(C)CC(=O)C1=C2OC(CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O)C(C)(C)O3152.2Standard non polar33892256
CyclomammeisinCC(C)CC(=O)C1=C2OC(CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O)C(C)(C)O3473.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cyclomammeisin,1TMS,isomer #1CC(C)CC(=O)C1=C2OC(C(C)(C)O)CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O[Si](C)(C)C3346.1Semi standard non polar33892256
Cyclomammeisin,1TMS,isomer #2CC(C)CC(=O)C1=C2OC(C(C)(C)O[Si](C)(C)C)CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O3343.6Semi standard non polar33892256
Cyclomammeisin,2TMS,isomer #1CC(C)CC(=O)C1=C2OC(C(C)(C)O[Si](C)(C)C)CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O[Si](C)(C)C3382.2Semi standard non polar33892256
Cyclomammeisin,1TBDMS,isomer #1CC(C)CC(=O)C1=C2OC(C(C)(C)O)CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O[Si](C)(C)C(C)(C)C3558.3Semi standard non polar33892256
Cyclomammeisin,1TBDMS,isomer #2CC(C)CC(=O)C1=C2OC(C(C)(C)O[Si](C)(C)C(C)(C)C)CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O3580.2Semi standard non polar33892256
Cyclomammeisin,2TBDMS,isomer #1CC(C)CC(=O)C1=C2OC(C(C)(C)O[Si](C)(C)C(C)(C)C)CC2=C2OC(=O)C=C(C3=CC=CC=C3)C2=C1O[Si](C)(C)C(C)(C)C3790.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cyclomammeisin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9205200000-5565a884c29b0c73cc3c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclomammeisin GC-MS (2 TMS) - 70eV, Positivesplash10-0ff9-9700240000-68d1510a934ce37269592017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclomammeisin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomammeisin 10V, Positive-QTOFsplash10-05fr-1006900000-d18e88396b34de62dbc12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomammeisin 20V, Positive-QTOFsplash10-05mk-4009200000-a52086b1ff6b9f2847942016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomammeisin 40V, Positive-QTOFsplash10-052f-7098000000-517f505fcd3da85515122016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomammeisin 10V, Negative-QTOFsplash10-00di-0004900000-8ec39bcb342ca485a11c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomammeisin 20V, Negative-QTOFsplash10-0079-3029400000-6f5a637151e0af78b4602016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomammeisin 40V, Negative-QTOFsplash10-067u-6159000000-2d608648a7440b756f392016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomammeisin 10V, Negative-QTOFsplash10-00di-0000900000-1a0e5664f3fc8624ecf12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomammeisin 20V, Negative-QTOFsplash10-00di-0018900000-20828ba55ef47f8315182021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomammeisin 40V, Negative-QTOFsplash10-066u-6039100000-b6704acaa6e6a02f33002021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomammeisin 10V, Positive-QTOFsplash10-00di-0000900000-83b5ca7a090ea30914172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomammeisin 20V, Positive-QTOFsplash10-00di-1008900000-05d2c09ad7325d5016a02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclomammeisin 40V, Positive-QTOFsplash10-0006-2059000000-cb294a2351b6d895221e2021-09-22Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDrw1822121
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