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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:04:13 UTC
Update Date2022-03-07 02:53:40 UTC
HMDB IDHMDB0033354
Secondary Accession Numbers
  • HMDB33354
Metabolite Identification
Common NameCassythicine
DescriptionCassythicine belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Cassythicine is a very strong basic compound (based on its pKa). Outside of the human body, cassythicine has been detected, but not quantified in, a few different foods, such as herbs and spices, sweet bay, and tea. This could make cassythicine a potential biomarker for the consumption of these foods.
Structure
Data?1563862393
Synonyms
ValueSource
(+)-CassythicineHMDB
9-Hydroxy-10-methoxy-1,2-methylenedioxyaporphineHMDB
N-MethylactinodaphnineHMDB
N-Methyl-actinodaphnineHMDB
Chemical FormulaC19H19NO4
Average Molecular Weight325.3585
Monoisotopic Molecular Weight325.131408101
IUPAC Name17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-16-ol
Traditional Name17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-16-ol
CAS Registry Number5890-28-8
SMILES
COC1=C(O)C=C2CC3N(C)CCC4=CC5=C(OCO5)C(C2=C1)=C34
InChI Identifier
InChI=1S/C19H19NO4/c1-20-4-3-10-7-16-19(24-9-23-16)18-12-8-15(22-2)14(21)6-11(12)5-13(20)17(10)18/h6-8,13,21H,3-5,9H2,1-2H3
InChI KeyMPWZJVCAMFAIGV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassAporphines
Sub ClassNot Available
Direct ParentAporphines
Alternative Parents
Substituents
  • Aporphine
  • Benzoquinoline
  • Phenanthrene
  • Naphthalene
  • Quinoline
  • Tetrahydroisoquinoline
  • Benzodioxole
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Acetal
  • Ether
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Amine
  • 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 Point210 - 212 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP2.36ALOGPS
logP2.86ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.7ChemAxon
pKa (Strongest Basic)7.07ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area51.16 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity90.24 m³·mol⁻¹ChemAxon
Polarizability34.98 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]+174.82831661259
DarkChem[M-H]-174.23231661259
DeepCCS[M-2H]-217.48430932474
DeepCCS[M+Na]+192.71130932474
AllCCS[M+H]+176.632859911
AllCCS[M+H-H2O]+173.332859911
AllCCS[M+NH4]+179.632859911
AllCCS[M+Na]+180.532859911
AllCCS[M-H]-183.832859911
AllCCS[M+Na-2H]-183.032859911
AllCCS[M+HCOO]-182.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CassythicineCOC1=C(O)C=C2CC3N(C)CCC4=CC5=C(OCO5)C(C2=C1)=C344215.6Standard polar33892256
CassythicineCOC1=C(O)C=C2CC3N(C)CCC4=CC5=C(OCO5)C(C2=C1)=C342678.8Standard non polar33892256
CassythicineCOC1=C(O)C=C2CC3N(C)CCC4=CC5=C(OCO5)C(C2=C1)=C343067.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cassythicine,1TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)CC1C3=C(C=C4OCOC4=C23)CCN1C2885.0Semi standard non polar33892256
Cassythicine,1TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)CC1C3=C(C=C4OCOC4=C23)CCN1C3121.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cassythicine GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-0193000000-b1bd7077267a5ae2859a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cassythicine GC-MS (1 TMS) - 70eV, Positivesplash10-0089-1109000000-d8fa1a1473a18df115752017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cassythicine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cassythicine 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 - Cassythicine 10V, Positive-QTOFsplash10-004i-0029000000-6a8f43699851886567cd2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cassythicine 20V, Positive-QTOFsplash10-004j-0097000000-067dc9f6d0bcca850a542015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cassythicine 40V, Positive-QTOFsplash10-00lr-0090000000-cbaa97460e0a17b3855c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cassythicine 10V, Negative-QTOFsplash10-00di-0009000000-7339316ec2025f970b932015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cassythicine 20V, Negative-QTOFsplash10-00di-0029000000-21dde708790249a3a9622015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cassythicine 40V, Negative-QTOFsplash10-0pdi-1092000000-0ceb6e7ae4b1a695dfbc2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cassythicine 10V, Positive-QTOFsplash10-004i-0009000000-8258216b4e41e9caadf22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cassythicine 20V, Positive-QTOFsplash10-004i-0019000000-fc549e0a0c8fe9675faa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cassythicine 40V, Positive-QTOFsplash10-00sj-0092000000-e131a57b405054fbe31f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cassythicine 10V, Negative-QTOFsplash10-00di-0009000000-fd8a579508e412fbe1142021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cassythicine 20V, Negative-QTOFsplash10-00di-0019000000-f9435823a721940ceaea2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cassythicine 40V, Negative-QTOFsplash10-00di-0097000000-29fd0bf8c0716a7a5aa12021-09-24Wishart 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 IDFDB011382
KNApSAcK IDC00001834
Chemspider ID3639935
KEGG Compound IDC09389
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4440434
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.. .