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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:25:31 UTC
Update Date2022-03-07 02:54:30 UTC
HMDB IDHMDB0035438
Secondary Accession Numbers
  • HMDB35438
Metabolite Identification
Common NamePromucosine
DescriptionPromucosine belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol. Promucosine has been detected, but not quantified in, beverages and fruits. This could make promucosine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Promucosine.
Structure
Data?1563862719
Synonyms
ValueSource
Methyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylic acidHMDB
Chemical FormulaC20H21NO5
Average Molecular Weight355.3844
Monoisotopic Molecular Weight355.141972787
IUPAC Namemethyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate
Traditional Namemethyl 10',11'-dimethoxy-4-oxo-5'-azaspiro[cyclohexane-1,2'-tricyclo[6.3.1.0⁴,¹²]dodecane]-1'(12'),2,5,8',10'-pentaene-5'-carboxylate
CAS Registry Number275355-87-8
SMILES
COC(=O)N1CCC2=CC(OC)=C(OC)C3=C2C1CC31C=CC(=O)C=C1
InChI Identifier
InChI=1S/C20H21NO5/c1-24-15-10-12-6-9-21(19(23)26-3)14-11-20(7-4-13(22)5-8-20)17(16(12)14)18(15)25-2/h4-5,7-8,10,14H,6,9,11H2,1-3H3
InChI KeyRRWYPLCSLKEVAO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as proaporphines. These are benzylisoquinoline derivatives characterized by the presence of a spirocyclohexane ring that can occur in various oxidation levels, from cyclohexadienone to cyclohexanol.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassProaporphines
Sub ClassNot Available
Direct ParentProaporphines
Alternative Parents
Substituents
  • Proaporphine
  • Tetrahydroisoquinoline
  • Indane
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Methylcarbamate
  • Carbamic acid ester
  • Cyclic ketone
  • Carbonic acid derivative
  • Ketone
  • Ether
  • Organoheterocyclic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point125 - 127 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.054 g/LALOGPS
logP2.05ALOGPS
logP2.3ChemAxon
logS-3.8ALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area65.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity98.16 m³·mol⁻¹ChemAxon
Polarizability36.8 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]+182.27231661259
DarkChem[M-H]-184.83231661259
DeepCCS[M-2H]-217.14530932474
DeepCCS[M+Na]+192.82630932474
AllCCS[M+H]+184.232859911
AllCCS[M+H-H2O]+181.232859911
AllCCS[M+NH4]+186.932859911
AllCCS[M+Na]+187.732859911
AllCCS[M-H]-189.332859911
AllCCS[M+Na-2H]-189.132859911
AllCCS[M+HCOO]-189.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PromucosineCOC(=O)N1CCC2=CC(OC)=C(OC)C3=C2C1CC31C=CC(=O)C=C14268.8Standard polar33892256
PromucosineCOC(=O)N1CCC2=CC(OC)=C(OC)C3=C2C1CC31C=CC(=O)C=C12859.0Standard non polar33892256
PromucosineCOC(=O)N1CCC2=CC(OC)=C(OC)C3=C2C1CC31C=CC(=O)C=C12986.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Promucosine GC-MS (Non-derivatized) - 70eV, Positivesplash10-01yy-0069000000-110fa642fd57962b902a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Promucosine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Promucosine 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 - Promucosine 10V, Positive-QTOFsplash10-0a4i-0009000000-6c2decad0f7309798ee52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promucosine 20V, Positive-QTOFsplash10-00di-0079000000-d513b278e27a820dc2802016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promucosine 40V, Positive-QTOFsplash10-032c-2090000000-c8148f11189e0a71f2532016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promucosine 10V, Negative-QTOFsplash10-0uk9-0009000000-cd2fc9b42733401fce6a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promucosine 20V, Negative-QTOFsplash10-00di-0019000000-2c12f5e0a12c414fead22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promucosine 40V, Negative-QTOFsplash10-0a4i-2097000000-39067db671ae6ba03ee92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promucosine 10V, Negative-QTOFsplash10-0udi-0009000000-3f012a8ceb78f6daa2f92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promucosine 20V, Negative-QTOFsplash10-01q9-0090000000-a7e5f45280c3cc9f1a352021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promucosine 40V, Negative-QTOFsplash10-0uec-1092000000-773b5d6d1edb733529732021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promucosine 10V, Positive-QTOFsplash10-0a4i-0009000000-d71201421eba67513e902021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promucosine 20V, Positive-QTOFsplash10-0ac0-0049000000-6ccfb231ff26ffacf6aa2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Promucosine 40V, Positive-QTOFsplash10-0ff1-1093000000-6eb98ec2efe1cf2f5ce82021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB014119
KNApSAcK IDC00027161
Chemspider ID10349245
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131751753
PDB IDNot Available
ChEBI ID174769
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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.. .