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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:04:31 UTC
Update Date2022-03-07 02:53:41 UTC
HMDB IDHMDB0033359
Secondary Accession Numbers
  • HMDB33359
Metabolite Identification
Common NameCryptodorine
DescriptionCryptodorine, also known as norneolitsine, 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. Cryptodorine is a very strong basic compound (based on its pKa). Outside of the human body, cryptodorine has been detected, but not quantified in, a few different foods, such as herbs and spices, sweet bay, and tea. This could make cryptodorine a potential biomarker for the consumption of these foods.
Structure
Data?1563862394
Synonyms
ValueSource
1,2:9,10-BismethylenedioxynoraporphineHMDB
NorneolitsineHMDB
Chemical FormulaC18H15NO4
Average Molecular Weight309.316
Monoisotopic Molecular Weight309.100107973
IUPAC Name5,7,19,21-tetraoxa-13-azahexacyclo[10.10.1.0²,¹⁰.0⁴,⁸.0¹⁶,²³.0¹⁸,²²]tricosa-1(23),2,4(8),9,16,18(22)-hexaene
Traditional Name5,7,19,21-tetraoxa-13-azahexacyclo[10.10.1.0²,¹⁰.0⁴,⁸.0¹⁶,²³.0¹⁸,²²]tricosa-1(23),2,4(8),9,16,18(22)-hexaene
CAS Registry Number41787-55-7
SMILES
C1OC2=C(O1)C=C1C(CC3NCCC4=CC5=C(OCO5)C1=C34)=C2
InChI Identifier
InChI=1S/C18H15NO4/c1-2-19-12-3-10-5-13-14(21-7-20-13)6-11(10)17-16(12)9(1)4-15-18(17)23-8-22-15/h4-6,12,19H,1-3,7-8H2
InChI KeyOMIDMWVBRZAVMK-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point219 - 221 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.14 g/LALOGPS
logP1.97ALOGPS
logP2.56ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)9.43ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area48.95 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity82.27 m³·mol⁻¹ChemAxon
Polarizability32.71 ųChemAxon
Number of Rings6ChemAxon
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]+170.26331661259
DarkChem[M-H]-167.25431661259
DeepCCS[M-2H]-215.60730932474
DeepCCS[M+Na]+190.93930932474
AllCCS[M+H]+171.932859911
AllCCS[M+H-H2O]+168.432859911
AllCCS[M+NH4]+175.132859911
AllCCS[M+Na]+176.032859911
AllCCS[M-H]-178.432859911
AllCCS[M+Na-2H]-177.232859911
AllCCS[M+HCOO]-176.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CryptodorineC1OC2=C(O1)C=C1C(CC3NCCC4=CC5=C(OCO5)C1=C34)=C24267.3Standard polar33892256
CryptodorineC1OC2=C(O1)C=C1C(CC3NCCC4=CC5=C(OCO5)C1=C34)=C22708.0Standard non polar33892256
CryptodorineC1OC2=C(O1)C=C1C(CC3NCCC4=CC5=C(OCO5)C1=C34)=C23044.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cryptodorine,1TMS,isomer #1C[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC2=C(C=C13)OCO22885.7Semi standard non polar33892256
Cryptodorine,1TMS,isomer #1C[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC2=C(C=C13)OCO22861.2Standard non polar33892256
Cryptodorine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC2=C(C=C13)OCO23104.0Semi standard non polar33892256
Cryptodorine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC2=C(C=C13)OCO23097.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cryptodorine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0096-0090000000-5b494b79b001715874392017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cryptodorine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cryptodorine 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 - Cryptodorine 10V, Negative-QTOFsplash10-0a4i-0019000000-78b89009c652721189112015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cryptodorine 20V, Negative-QTOFsplash10-0a4i-0069000000-3eb29ebf0fef6374ecaa2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cryptodorine 40V, Negative-QTOFsplash10-01p6-0190000000-cef99ce841654a344a1f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cryptodorine 10V, Negative-QTOFsplash10-0a4i-0009000000-032c4ad1d38e89ca23122021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cryptodorine 20V, Negative-QTOFsplash10-0a4i-0039000000-1c4e174e83b5ed3fd4f02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cryptodorine 40V, Negative-QTOFsplash10-002f-0091000000-46c4cbe431c35f2f121d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cryptodorine 10V, Positive-QTOFsplash10-03di-0039000000-8a6efb2179eb428d154b2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cryptodorine 20V, Positive-QTOFsplash10-03di-0095000000-835e4f20b57c086df87e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cryptodorine 40V, Positive-QTOFsplash10-00m0-0290000000-2d7a350c10b6a1b9825f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cryptodorine 10V, Positive-QTOFsplash10-03di-0009000000-ca0f623accd9ac4b341d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cryptodorine 20V, Positive-QTOFsplash10-03di-0009000000-41b6b27220c1b707b2842021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cryptodorine 40V, Positive-QTOFsplash10-03ec-0193000000-a41d4d21118ff411e2a82021-09-24Wishart 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 IDFDB011387
KNApSAcK IDNot Available
Chemspider ID9613142
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11438278
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.. .