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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:58:28 UTC
Update Date2022-03-07 02:55:51 UTC
HMDB IDHMDB0038642
Secondary Accession Numbers
  • HMDB38642
Metabolite Identification
Common NameFumitremorgin C
DescriptionFumitremorgin C, also known as tryptoquivaline or SM-Q, belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. Fumitremorgin C is produced by Aspergillus fumigatus and Neosartorya fischeri. Fumitremorgin C is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563863232
Synonyms
ValueSource
TryptoquivalineChEBI
SM-QHMDB
Tryproquivaline L (9'r-(9'alpha(r*),9'abeta))-isomerMeSH
Tryproquivaline m (2's-(2'alpha,9'alpha(4S*(s*)),9'abeta))-isomerMeSH
Tryproquivaline N (2's-(2'alpha,9'alpha(r*),9'abeta))-isomerMeSH
Tryproquivaline m (2's-(2'alpha,9'alpha(4R*(s*)),9'abeta))-isomerMeSH
Tryproquivaline D (2's-(2'alpha,9'alpha(4R*(s*)),9'abeta))-isomerMeSH
Tryproquivaline L (9'r-(9'alpha(s*),9'abeta))-isomerMeSH
Chemical FormulaC22H25N3O3
Average Molecular Weight379.4522
Monoisotopic Molecular Weight379.189591681
IUPAC Name(1S,12S,15S)-7-methoxy-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁵,¹⁹]icosa-3(11),4,6,8-tetraene-14,20-dione
Traditional Name(1S,12S,15S)-7-methoxy-12-(2-methylprop-1-en-1-yl)-10,13,19-triazapentacyclo[11.7.0.0³,¹¹.0⁴,⁹.0¹⁵,¹⁹]icosa-3(11),4,6,8-tetraene-14,20-dione
CAS Registry Number118974-02-0
SMILES
COC1=CC=C2C(NC3=C2C[C@@H]2N([C@H]3C=C(C)C)C(=O)[C@@H]3CCCN3C2=O)=C1
InChI Identifier
InChI=1S/C22H25N3O3/c1-12(2)9-18-20-15(14-7-6-13(28-3)10-16(14)23-20)11-19-21(26)24-8-4-5-17(24)22(27)25(18)19/h6-7,9-10,17-19,23H,4-5,8,11H2,1-3H3/t17-,18-,19-/m0/s1
InChI KeyDBEYVIGIPJSTOR-FHWLQOOXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyridoindoles
Direct ParentBeta carbolines
Alternative Parents
Substituents
  • Beta-carboline
  • Alpha-amino acid or derivatives
  • 3-alkylindole
  • Indole
  • Anisole
  • Dioxopiperazine
  • 2,5-dioxopiperazine
  • Alkyl aryl ether
  • N-alkylpiperazine
  • 1,4-diazinane
  • Piperazine
  • Benzenoid
  • Pyrrolidine
  • Pyrrole
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Carboxamide group
  • Lactam
  • Azacycle
  • Ether
  • Carboxylic acid derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point259.5 - 260.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.39 g/LALOGPS
logP2.2ALOGPS
logP2.11ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)15.11ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area65.64 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity106.57 m³·mol⁻¹ChemAxon
Polarizability42.52 ųChemAxon
Number of Rings5ChemAxon
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]+187.48831661259
DarkChem[M-H]-188.41431661259
DeepCCS[M+H]+198.00930932474
DeepCCS[M-H]-195.61430932474
DeepCCS[M-2H]-228.49830932474
DeepCCS[M+Na]+203.94230932474
AllCCS[M+H]+192.832859911
AllCCS[M+H-H2O]+190.232859911
AllCCS[M+NH4]+195.332859911
AllCCS[M+Na]+196.032859911
AllCCS[M-H]-196.532859911
AllCCS[M+Na-2H]-196.632859911
AllCCS[M+HCOO]-196.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Fumitremorgin CCOC1=CC=C2C(NC3=C2C[C@@H]2N([C@H]3C=C(C)C)C(=O)[C@@H]3CCCN3C2=O)=C14824.4Standard polar33892256
Fumitremorgin CCOC1=CC=C2C(NC3=C2C[C@@H]2N([C@H]3C=C(C)C)C(=O)[C@@H]3CCCN3C2=O)=C13606.5Standard non polar33892256
Fumitremorgin CCOC1=CC=C2C(NC3=C2C[C@@H]2N([C@H]3C=C(C)C)C(=O)[C@@H]3CCCN3C2=O)=C13638.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Fumitremorgin C,1TMS,isomer #1COC1=CC=C2C3=C([C@H](C=C(C)C)N4C(=O)[C@@H]5CCCN5C(=O)[C@@H]4C3)N([Si](C)(C)C)C2=C13394.4Semi standard non polar33892256
Fumitremorgin C,1TMS,isomer #1COC1=CC=C2C3=C([C@H](C=C(C)C)N4C(=O)[C@@H]5CCCN5C(=O)[C@@H]4C3)N([Si](C)(C)C)C2=C13295.6Standard non polar33892256
Fumitremorgin C,1TBDMS,isomer #1COC1=CC=C2C3=C([C@H](C=C(C)C)N4C(=O)[C@@H]5CCCN5C(=O)[C@@H]4C3)N([Si](C)(C)C(C)(C)C)C2=C13520.7Semi standard non polar33892256
Fumitremorgin C,1TBDMS,isomer #1COC1=CC=C2C3=C([C@H](C=C(C)C)N4C(=O)[C@@H]5CCCN5C(=O)[C@@H]4C3)N([Si](C)(C)C(C)(C)C)C2=C13531.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Fumitremorgin C GC-MS (Non-derivatized) - 70eV, Positivesplash10-0w2a-8095000000-7194759fc8623292bdeb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fumitremorgin C GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Fumitremorgin C 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 - Fumitremorgin C 10V, Positive-QTOFsplash10-001i-0009000000-0f0c39953390b4eda9912017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fumitremorgin C 20V, Positive-QTOFsplash10-001i-2119000000-673774e3d3fbffa8e3342017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fumitremorgin C 40V, Positive-QTOFsplash10-05fu-9130000000-21de2d5497bc35a45a632017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fumitremorgin C 10V, Negative-QTOFsplash10-004i-0009000000-36a2fe9ac638e57b2fc22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fumitremorgin C 20V, Negative-QTOFsplash10-004i-7079000000-092c074c39d9e22324d62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fumitremorgin C 40V, Negative-QTOFsplash10-0gb9-9080000000-e123deaf8b2815821b012017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fumitremorgin C 10V, Positive-QTOFsplash10-001i-0009000000-bd5ffa7b6ba5e943ad002021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fumitremorgin C 20V, Positive-QTOFsplash10-001i-0009000000-5642131e191c150db5b42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fumitremorgin C 40V, Positive-QTOFsplash10-00bi-3139000000-f79890b4f8399c58e00e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fumitremorgin C 10V, Negative-QTOFsplash10-004i-0009000000-478cc77e0dbfe3e7b7cb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fumitremorgin C 20V, Negative-QTOFsplash10-004i-0009000000-16ac16601dba9cca90752021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Fumitremorgin C 40V, Negative-QTOFsplash10-004i-1229000000-742943f1d35328892cb72021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-23Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-23Wishart 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 IDFDB018037
KNApSAcK IDC00011298
Chemspider ID357779
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound403923
PDB IDNot Available
ChEBI ID72763
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.. .