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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:53 UTC
Update Date2022-03-07 02:52:29 UTC
HMDB IDHMDB0030281
Secondary Accession Numbers
  • HMDB30281
Metabolite Identification
Common NameCalycanthidine
DescriptionCalycanthidine belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Based on a literature review a significant number of articles have been published on Calycanthidine.
Structure
Data?1563861963
Synonyms
ValueSource
(+)-CalycanthidineHMDB
Chemical FormulaC23H28N4
Average Molecular Weight360.4952
Monoisotopic Molecular Weight360.231396916
IUPAC Name1,8-dimethyl-3a-{1-methyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-3a-yl}-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indole
Traditional Namecalycanthidine
CAS Registry Number5516-85-8
SMILES
CN1CCC2(C1NC1=C2C=CC=C1)C12CCN(C)C1N(C)C1=C2C=CC=C1
InChI Identifier
InChI=1S/C23H28N4/c1-25-14-12-22(16-8-4-6-10-18(16)24-20(22)25)23-13-15-26(2)21(23)27(3)19-11-7-5-9-17(19)23/h4-11,20-21,24H,12-15H2,1-3H3
InChI KeyGSQUXSFTXJRLQJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyrroloindoles
Direct ParentPyrroloindoles
Alternative Parents
Substituents
  • Pyrroloindole
  • Indole
  • Dihydroindole
  • Dialkylarylamine
  • Secondary aliphatic/aromatic amine
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Pyrrole
  • Secondary amine
  • Azacycle
  • Amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point142 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility450.8 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.025 g/LALOGPS
logP3.68ALOGPS
logP3.48ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)15.86ChemAxon
pKa (Strongest Basic)7.75ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area21.75 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity112.14 m³·mol⁻¹ChemAxon
Polarizability40.6 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+185.86431661259
DarkChem[M-H]-181.85231661259
DeepCCS[M-2H]-214.75130932474
DeepCCS[M+Na]+189.97830932474
AllCCS[M+H]+187.732859911
AllCCS[M+H-H2O]+184.732859911
AllCCS[M+NH4]+190.432859911
AllCCS[M+Na]+191.232859911
AllCCS[M-H]-199.232859911
AllCCS[M+Na-2H]-198.832859911
AllCCS[M+HCOO]-198.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CalycanthidineCN1CCC2(C1NC1=C2C=CC=C1)C12CCN(C)C1N(C)C1=C2C=CC=C13999.5Standard polar33892256
CalycanthidineCN1CCC2(C1NC1=C2C=CC=C1)C12CCN(C)C1N(C)C1=C2C=CC=C13004.1Standard non polar33892256
CalycanthidineCN1CCC2(C1NC1=C2C=CC=C1)C12CCN(C)C1N(C)C1=C2C=CC=C12713.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Calycanthidine,1TMS,isomer #1CN1CCC2(C34CCN(C)C3N([Si](C)(C)C)C3=CC=CC=C34)C3=CC=CC=C3N(C)C122900.9Semi standard non polar33892256
Calycanthidine,1TMS,isomer #1CN1CCC2(C34CCN(C)C3N([Si](C)(C)C)C3=CC=CC=C34)C3=CC=CC=C3N(C)C122986.3Standard non polar33892256
Calycanthidine,1TBDMS,isomer #1CN1CCC2(C34CCN(C)C3N([Si](C)(C)C(C)(C)C)C3=CC=CC=C34)C3=CC=CC=C3N(C)C123092.6Semi standard non polar33892256
Calycanthidine,1TBDMS,isomer #1CN1CCC2(C34CCN(C)C3N([Si](C)(C)C(C)(C)C)C3=CC=CC=C34)C3=CC=CC=C3N(C)C123311.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Calycanthidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-0409000000-5bd6c4ccbdc9ecd9862c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Calycanthidine 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 - Calycanthidine 10V, Positive-QTOFsplash10-03di-0009000000-d8f2e59fa213947d12e42016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calycanthidine 20V, Positive-QTOFsplash10-03di-0009000000-7c8c5c3b0b1d91e90ffb2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calycanthidine 40V, Positive-QTOFsplash10-0aor-5829000000-d9bbb5e867f7f2081a002016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calycanthidine 10V, Negative-QTOFsplash10-0a4i-0509000000-43f90f4b702f67ebe8072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calycanthidine 20V, Negative-QTOFsplash10-0a4i-1209000000-86d66e8eb85e0fb3f4712016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calycanthidine 40V, Negative-QTOFsplash10-05fu-0914000000-88052475260170f8d4b22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calycanthidine 10V, Positive-QTOFsplash10-03di-0009000000-e146292dc6ccb0e82d802021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calycanthidine 20V, Positive-QTOFsplash10-03di-0009000000-ed549a23f9f1c7146fea2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calycanthidine 40V, Positive-QTOFsplash10-0w29-1249000000-1c98ba0a4e47299457132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calycanthidine 10V, Negative-QTOFsplash10-0a4i-0009000000-939a393ff3810ce2c5672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calycanthidine 20V, Negative-QTOFsplash10-0a4i-0009000000-939a393ff3810ce2c5672021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Calycanthidine 40V, Negative-QTOFsplash10-05fr-1901000000-2777806116f7483a07f02021-09-22Wishart 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 IDFDB002114
KNApSAcK IDC00001700
Chemspider ID520812
KEGG Compound IDC09097
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound599113
PDB IDNot Available
ChEBI ID38970
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1818671
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.. .