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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:59 UTC
Update Date2022-03-07 02:52:41 UTC
HMDB IDHMDB0030781
Secondary Accession Numbers
  • HMDB30781
Metabolite Identification
Common NameIsomammein
DescriptionIsomammein, also known as mammea b/aa, belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Based on a literature review very few articles have been published on Isomammein.
Structure
Data?1563862036
Synonyms
ValueSource
5,7-Dihydroxy-6-isovaleryl-8-(3-methyl-2-butenyl)-4-propylcoumarin, 8ciHMDB
5,7-Dihydroxy-8-(3-methyl-2-butenyl)-6-(3-methyl-1-oxobutyl)-4-propyl-2H-1-benzopyran-2-one, 9ciHMDB
Mammea b/aaHMDB
Chemical FormulaC22H28O5
Average Molecular Weight372.4547
Monoisotopic Molecular Weight372.193674006
IUPAC Name5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-6-(3-methylbutanoyl)-4-propyl-2H-chromen-2-one
Traditional Name5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-6-(3-methylbutanoyl)-4-propylchromen-2-one
CAS Registry Number478-67-1
SMILES
CCCC1=CC(=O)OC2=C(CC=C(C)C)C(O)=C(C(=O)CC(C)C)C(O)=C12
InChI Identifier
InChI=1S/C22H28O5/c1-6-7-14-11-17(24)27-22-15(9-8-12(2)3)20(25)19(21(26)18(14)22)16(23)10-13(4)5/h8,11,13,25-26H,6-7,9-10H2,1-5H3
InChI KeyVXFHCMCZMKQIMR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent7-hydroxycoumarins
Alternative Parents
Substituents
  • 7-hydroxycoumarin
  • Butyrophenone
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Ketone
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • 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 Point109 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.016 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP4.39ALOGPS
logP6.38ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)8.05ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity107.42 m³·mol⁻¹ChemAxon
Polarizability41.6 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.5631661259
DarkChem[M-H]-190.06231661259
DeepCCS[M-2H]-228.30530932474
DeepCCS[M+Na]+203.53430932474
AllCCS[M+H]+189.632859911
AllCCS[M+H-H2O]+186.932859911
AllCCS[M+NH4]+192.132859911
AllCCS[M+Na]+192.832859911
AllCCS[M-H]-197.432859911
AllCCS[M+Na-2H]-197.832859911
AllCCS[M+HCOO]-198.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsomammeinCCCC1=CC(=O)OC2=C(CC=C(C)C)C(O)=C(C(=O)CC(C)C)C(O)=C123682.6Standard polar33892256
IsomammeinCCCC1=CC(=O)OC2=C(CC=C(C)C)C(O)=C(C(=O)CC(C)C)C(O)=C122719.7Standard non polar33892256
IsomammeinCCCC1=CC(=O)OC2=C(CC=C(C)C)C(O)=C(C(=O)CC(C)C)C(O)=C122932.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isomammein,1TMS,isomer #1CCCC1=CC(=O)OC2=C(CC=C(C)C)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C(O)=C122756.6Semi standard non polar33892256
Isomammein,1TMS,isomer #2CCCC1=CC(=O)OC2=C(CC=C(C)C)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C)=C122773.8Semi standard non polar33892256
Isomammein,2TMS,isomer #1CCCC1=CC(=O)OC2=C(CC=C(C)C)C(O[Si](C)(C)C)=C(C(=O)CC(C)C)C(O[Si](C)(C)C)=C122785.3Semi standard non polar33892256
Isomammein,1TBDMS,isomer #1CCCC1=CC(=O)OC2=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)CC(C)C)C(O)=C122977.8Semi standard non polar33892256
Isomammein,1TBDMS,isomer #2CCCC1=CC(=O)OC2=C(CC=C(C)C)C(O)=C(C(=O)CC(C)C)C(O[Si](C)(C)C(C)(C)C)=C122985.8Semi standard non polar33892256
Isomammein,2TBDMS,isomer #1CCCC1=CC(=O)OC2=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)CC(C)C)C(O[Si](C)(C)C(C)(C)C)=C123195.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isomammein GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ar3-2029000000-35c0b259227446b78b502017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomammein GC-MS (2 TMS) - 70eV, Positivesplash10-0udi-5422970000-8e2aee001fdcb3d9338b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomammein GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isomammein 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 - Isomammein 10V, Positive-QTOFsplash10-00di-0009000000-0e97ff129de44e6255be2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomammein 20V, Positive-QTOFsplash10-014i-4049000000-9949af007ea5dedaa7132016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomammein 40V, Positive-QTOFsplash10-0aor-5091000000-9c2d605c04f162ac54e32016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomammein 10V, Negative-QTOFsplash10-00di-0019000000-07e27119e6aed625b35b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomammein 20V, Negative-QTOFsplash10-0079-4098000000-f831c2468825e5e54e742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomammein 40V, Negative-QTOFsplash10-0a4u-9183000000-38753ae783d3967903722016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomammein 10V, Positive-QTOFsplash10-00di-0009000000-2ba4fbcce42fdd3b689e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomammein 20V, Positive-QTOFsplash10-00dl-0019000000-56a0a6e3f2c27a4949322021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomammein 40V, Positive-QTOFsplash10-0f7d-2093000000-0f1b131b3954addd24eb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomammein 10V, Negative-QTOFsplash10-00di-0009000000-0f67c9388d63ae2a73ac2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomammein 20V, Negative-QTOFsplash10-00di-0029000000-56a52dc649ed327374042021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isomammein 40V, Negative-QTOFsplash10-000f-6296000000-7fa6b4be9e64aacf9d5f2021-09-25Wishart 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 IDFDB002718
KNApSAcK IDNot Available
Chemspider ID4678000
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5748528
PDB IDNot Available
ChEBI ID1177617
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1417931
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
Isomammein → 3,4,5-trihydroxy-6-{[7-hydroxy-8-(3-methylbut-2-en-1-yl)-6-(3-methylbutanoyl)-2-oxo-4-propyl-2H-chromen-5-yl]oxy}oxane-2-carboxylic aciddetails
Isomammein → 3,4,5-trihydroxy-6-{[5-hydroxy-8-(3-methylbut-2-en-1-yl)-6-(3-methylbutanoyl)-2-oxo-4-propyl-2H-chromen-7-yl]oxy}oxane-2-carboxylic aciddetails