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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:11:07 UTC
Update Date2022-03-07 02:55:56 UTC
HMDB IDHMDB0038837
Secondary Accession Numbers
  • HMDB38837
Metabolite Identification
Common Name(R)-Mahanine
Description(R)-Mahanine, also known as bisisomahanine, 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 (R)-Mahanine has been detected, but not quantified in, herbs and spices. This could make (R)-mahanine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)-Mahanine.
Structure
Data?1563863267
Synonyms
ValueSource
BisisomahanineHMDB
IsomahanineHMDB
MahanineHMDB
Chemical FormulaC23H25NO2
Average Molecular Weight347.4501
Monoisotopic Molecular Weight347.188529049
IUPAC Name3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-3H,11H-pyrano[3,2-a]carbazol-9-ol
Traditional Name3,5-dimethyl-3-(4-methylpent-3-en-1-yl)-11H-pyrano[3,2-a]carbazol-9-ol
CAS Registry Number28360-49-8
SMILES
CC(C)=CCCC1(C)OC2=C(C)C=C3C(NC4=C3C=CC(O)=C4)=C2C=C1
InChI Identifier
InChI=1S/C23H25NO2/c1-14(2)6-5-10-23(4)11-9-18-21-19(12-15(3)22(18)26-23)17-8-7-16(25)13-20(17)24-21/h6-9,11-13,24-25H,5,10H2,1-4H3
InChI KeyDWMBXHWBPZZCTN-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
  • Benzopyran
  • 1-benzopyran
  • Hydroxyindole
  • Indole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Oxacycle
  • Azacycle
  • Ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • 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 Point98 - 100 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00023 g/LALOGPS
logP5.88ALOGPS
logP5.94ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)9.77ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area45.25 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity108.61 m³·mol⁻¹ChemAxon
Polarizability41.25 ųChemAxon
Number of Rings4ChemAxon
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]+188.91631661259
DarkChem[M-H]-185.2531661259
DeepCCS[M+H]+193.830932474
DeepCCS[M-H]-191.44230932474
DeepCCS[M-2H]-225.5230932474
DeepCCS[M+Na]+200.81130932474
AllCCS[M+H]+189.132859911
AllCCS[M+H-H2O]+186.032859911
AllCCS[M+NH4]+192.132859911
AllCCS[M+Na]+192.932859911
AllCCS[M-H]-186.832859911
AllCCS[M+Na-2H]-186.232859911
AllCCS[M+HCOO]-185.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-MahanineCC(C)=CCCC1(C)OC2=C(C)C=C3C(NC4=C3C=CC(O)=C4)=C2C=C14227.0Standard polar33892256
(R)-MahanineCC(C)=CCCC1(C)OC2=C(C)C=C3C(NC4=C3C=CC(O)=C4)=C2C=C13301.9Standard non polar33892256
(R)-MahanineCC(C)=CCCC1(C)OC2=C(C)C=C3C(NC4=C3C=CC(O)=C4)=C2C=C13196.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-Mahanine,1TMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(O1)C(C)=CC1=C2[NH]C2=CC(O[Si](C)(C)C)=CC=C213356.7Semi standard non polar33892256
(R)-Mahanine,1TMS,isomer #2CC(C)=CCCC1(C)C=CC2=C(O1)C(C)=CC1=C2N([Si](C)(C)C)C2=CC(O)=CC=C123322.2Semi standard non polar33892256
(R)-Mahanine,2TMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(O1)C(C)=CC1=C2N([Si](C)(C)C)C2=CC(O[Si](C)(C)C)=CC=C123283.7Semi standard non polar33892256
(R)-Mahanine,2TMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(O1)C(C)=CC1=C2N([Si](C)(C)C)C2=CC(O[Si](C)(C)C)=CC=C122973.5Standard non polar33892256
(R)-Mahanine,1TBDMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(O1)C(C)=CC1=C2[NH]C2=CC(O[Si](C)(C)C(C)(C)C)=CC=C213550.2Semi standard non polar33892256
(R)-Mahanine,1TBDMS,isomer #2CC(C)=CCCC1(C)C=CC2=C(O1)C(C)=CC1=C2N([Si](C)(C)C(C)(C)C)C2=CC(O)=CC=C123426.0Semi standard non polar33892256
(R)-Mahanine,2TBDMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(O1)C(C)=CC1=C2N([Si](C)(C)C(C)(C)C)C2=CC(O[Si](C)(C)C(C)(C)C)=CC=C123607.2Semi standard non polar33892256
(R)-Mahanine,2TBDMS,isomer #1CC(C)=CCCC1(C)C=CC2=C(O1)C(C)=CC1=C2N([Si](C)(C)C(C)(C)C)C2=CC(O[Si](C)(C)C(C)(C)C)=CC=C123378.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Mahanine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9214000000-ecc7459fbb6a3333440e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Mahanine GC-MS (1 TMS) - 70eV, Positivesplash10-1000-9013500000-01844e4a39d1dde8fb512017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Mahanine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mahanine LC-ESI-qTof , Positive-QTOFsplash10-0292-0900000000-c425a61748288dae7b6d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Mahanine , positive-QTOFsplash10-03di-0390000000-7c424603fbb8bdf391302017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 10V, Positive-QTOFsplash10-0002-1029000000-0a3f7a9ac2a57ed105082015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 20V, Positive-QTOFsplash10-00os-2192000000-4b3971b7141d322c1f7b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 40V, Positive-QTOFsplash10-0gi1-9870000000-4f0599983bcfb7f4d3eb2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 10V, Positive-QTOFsplash10-0002-1029000000-0a3f7a9ac2a57ed105082015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 20V, Positive-QTOFsplash10-00os-2192000000-4b3971b7141d322c1f7b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 40V, Positive-QTOFsplash10-0gi1-9870000000-4f0599983bcfb7f4d3eb2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 10V, Negative-QTOFsplash10-0002-0019000000-01a730bb3eaf3d6732222015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 20V, Negative-QTOFsplash10-0002-0149000000-185dc3c50e9455fcfab72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 40V, Negative-QTOFsplash10-01ox-0941000000-4d5d8776720ac4a699fe2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 10V, Negative-QTOFsplash10-0002-0019000000-01a730bb3eaf3d6732222015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 20V, Negative-QTOFsplash10-0002-0149000000-185dc3c50e9455fcfab72015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 40V, Negative-QTOFsplash10-01ox-0941000000-4d5d8776720ac4a699fe2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 10V, Negative-QTOFsplash10-0002-0009000000-05ac4a26ff2e3947323e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 20V, Negative-QTOFsplash10-0002-0019000000-e07f91ad80401d55ea3f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 40V, Negative-QTOFsplash10-01q9-1093000000-b71579fae19e6ca8719d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 10V, Positive-QTOFsplash10-0002-0059000000-1b6cda55ddf10624b1332021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 20V, Positive-QTOFsplash10-002b-0096000000-69ec1ad6551bafc2f6932021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Mahanine 40V, Positive-QTOFsplash10-07bu-4190000000-de7ae130401929caab492021-09-24Wishart 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 IDFDB018272
KNApSAcK IDNot Available
Chemspider ID332794
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound375151
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.. .