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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:56 UTC
Update Date2022-03-07 02:52:29 UTC
HMDB IDHMDB0030289
Secondary Accession Numbers
  • HMDB30289
Metabolite Identification
Common NameCurrayanine
DescriptionCurrayanine, also known as cyclomahanimbine or murrayazolidine, belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. Currayanine is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, currayanine has been detected, but not quantified in, herbs and spices. This could make currayanine a potential biomarker for the consumption of these foods.
Structure
Data?1563861964
Synonyms
ValueSource
1,2,3,4,5,13-Hexahydro-5,7-dimethyl-2-(1-methylethenyl)-1,5-methanooxocino[3,2-a]carbazole, 9ciHMDB
CurryanineHMDB
CyclomahanimbineHMDB
MurrayazolidineHMDB
Chemical FormulaC23H25NO
Average Molecular Weight331.4507
Monoisotopic Molecular Weight331.193614427
IUPAC Name13,16-dimethyl-19-(prop-1-en-2-yl)-15-oxa-4-azapentacyclo[14.3.1.0²,¹⁴.0³,¹¹.0⁵,¹⁰]icosa-2(14),3(11),5(10),6,8,12-hexaene
Traditional Name13,16-dimethyl-19-(prop-1-en-2-yl)-15-oxa-4-azapentacyclo[14.3.1.0²,¹⁴.0³,¹¹.0⁵,¹⁰]icosa-2(14),3(11),5(10),6,8,12-hexaene
CAS Registry Number25488-33-9
SMILES
CC(=C)C1CCC2(C)CC1C1=C(O2)C(C)=CC2=C1NC1=C2C=CC=C1
InChI Identifier
InChI=1S/C23H25NO/c1-13(2)15-9-10-23(4)12-18(15)20-21-17(11-14(3)22(20)25-23)16-7-5-6-8-19(16)24-21/h5-8,11,15,18,24H,1,9-10,12H2,2-4H3
InChI KeyKXNHNLQCCJZSEK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassCarbazoles
Direct ParentCarbazoles
Alternative Parents
Substituents
  • Carbazole
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Indole
  • Alkyl aryl ether
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Ether
  • Oxacycle
  • Azacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point146 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.0e-05 g/LALOGPS
logP5.94ALOGPS
logP5.65ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)15.13ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area25.02 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity102.69 m³·mol⁻¹ChemAxon
Polarizability39.33 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+179.22831661259
DarkChem[M-H]-176.70131661259
DeepCCS[M+H]+183.51330932474
DeepCCS[M-H]-181.15530932474
DeepCCS[M-2H]-215.1230932474
DeepCCS[M+Na]+190.73530932474
AllCCS[M+H]+181.332859911
AllCCS[M+H-H2O]+178.132859911
AllCCS[M+NH4]+184.332859911
AllCCS[M+Na]+185.132859911
AllCCS[M-H]-190.532859911
AllCCS[M+Na-2H]-189.632859911
AllCCS[M+HCOO]-188.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CurrayanineCC(=C)C1CCC2(C)CC1C1=C(O2)C(C)=CC2=C1NC1=C2C=CC=C13733.1Standard polar33892256
CurrayanineCC(=C)C1CCC2(C)CC1C1=C(O2)C(C)=CC2=C1NC1=C2C=CC=C12916.5Standard non polar33892256
CurrayanineCC(=C)C1CCC2(C)CC1C1=C(O2)C(C)=CC2=C1NC1=C2C=CC=C12949.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Currayanine,1TMS,isomer #1C=C(C)C1CCC2(C)CC1C1=C3C(=CC(C)=C1O2)C1=CC=CC=C1N3[Si](C)(C)C3215.6Semi standard non polar33892256
Currayanine,1TMS,isomer #1C=C(C)C1CCC2(C)CC1C1=C3C(=CC(C)=C1O2)C1=CC=CC=C1N3[Si](C)(C)C2695.1Standard non polar33892256
Currayanine,1TBDMS,isomer #1C=C(C)C1CCC2(C)CC1C1=C3C(=CC(C)=C1O2)C1=CC=CC=C1N3[Si](C)(C)C(C)(C)C3322.9Semi standard non polar33892256
Currayanine,1TBDMS,isomer #1C=C(C)C1CCC2(C)CC1C1=C3C(=CC(C)=C1O2)C1=CC=CC=C1N3[Si](C)(C)C(C)(C)C2883.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Currayanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-016u-7097000000-d6947941c3cd5ea130c12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Currayanine 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 - Currayanine 10V, Positive-QTOFsplash10-001i-0019000000-055cebb0bc5a1088145c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Currayanine 20V, Positive-QTOFsplash10-001i-3269000000-800a5e5c17dffdfe7f942016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Currayanine 40V, Positive-QTOFsplash10-00lr-9311000000-e531f03d8ccc1e7c973e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Currayanine 10V, Negative-QTOFsplash10-001i-0009000000-f0df4930bbda5e26c2872016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Currayanine 20V, Negative-QTOFsplash10-001i-0109000000-3cf79081d7752fb160272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Currayanine 40V, Negative-QTOFsplash10-004i-0954000000-ac7f67442495d8424fd82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Currayanine 10V, Positive-QTOFsplash10-001i-0029000000-7833300a766e7b2ef23e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Currayanine 20V, Positive-QTOFsplash10-001i-0049000000-ff929612150ce0b943c82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Currayanine 40V, Positive-QTOFsplash10-0032-3894000000-42d681fc6249ac4b33a12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Currayanine 10V, Negative-QTOFsplash10-001i-0009000000-1e05108e34c227de397d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Currayanine 20V, Negative-QTOFsplash10-001i-0009000000-38d68123ebff3db1c9ee2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Currayanine 40V, Negative-QTOFsplash10-01p2-0492000000-1d048e14483dd57c29842021-09-22Wishart 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 IDFDB002125
KNApSAcK IDNot Available
Chemspider ID332787
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound375144
PDB IDNot Available
ChEBI IDNot Available
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.. .