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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:35:19 UTC
Update Date2022-03-07 02:52:27 UTC
HMDB IDHMDB0030184
Secondary Accession Numbers
  • HMDB30184
Metabolite Identification
Common Name(S)-Isocorydine
Description(S)-Isocorydine, also known as S-artabotrine or S-luteanine, 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 (S)-Isocorydine is a very strong basic compound (based on its pKa). Outside of the human body, (S)-isocorydine has been detected, but not quantified in, cherimoya and poppies. This could make (S)-isocorydine a potential biomarker for the consumption of these foods. In addition, isocorydine treatment led to a decrease in the percentage of CD133+ PLC/PRF/5 cells (S)-Isocorydine is a potentially toxic compound. No indication of carcinogenicity to humans (not listed by IARC). Furthermore, G2/M arrest induced by ICD can be disrupted by Chk1 siRNA but not by Chk2 siRNA. Interestingly, isocorydine treatment dramatically decreased the tumorigenicity of SMMC-7721 and Huh7 cells. The phosphorylation levels of Chk1 and Chk2 were increased after ICD treatment. Isocorydine induces G2/M phase arrest by increasing cyclin B1 and p-CDK1 expression levels, which was caused by decreasing the expression and inhibiting the activation of Cdc25C.
Structure
Data?1563861950
Synonyms
ValueSource
(+)-IsocorydineHMDB
(+)-(S)-IsocorydineHMDB
(S)-(+)-IsocorydineHMDB
1,2,10-Trimethoxy-6a-alpha-aporphin-11-olHMDB
L-(+)-IsocorydineHMDB
S-ArtabotrineHMDB
S-LuteanineHMDB
Isocorydine hydrochloride, (S)-isomerHMDB
Isocorydine, (R)-isomerHMDB
Isocorydine, (S)-isomerHMDB
Chemical FormulaC20H23NO4
Average Molecular Weight341.4009
Monoisotopic Molecular Weight341.162708229
IUPAC Name(9S)-4,15,16-trimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,13(17),14-hexaen-3-ol
Traditional Name(9S)-4,15,16-trimethoxy-10-methyl-10-azatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2,4,6,13(17),14-hexaen-3-ol
CAS Registry Number475-67-2
SMILES
[H][C@@]12CC3=CC=C(OC)C(O)=C3C3=C(OC)C(OC)=CC(CCN1C)=C23
InChI Identifier
InChI=1S/C20H23NO4/c1-21-8-7-12-10-15(24-3)20(25-4)18-16(12)13(21)9-11-5-6-14(23-2)19(22)17(11)18/h5-6,10,13,22H,7-9H2,1-4H3/t13-/m0/s1
InChI KeyQELDJEKNFOQJOY-ZDUSSCGKSA-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
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point185 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available181.909http://allccs.zhulab.cn/database/detail?ID=AllCCS00001374
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.83ALOGPS
logP2.92ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)6.7ChemAxon
pKa (Strongest Basic)9.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area51.16 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity97.4 m³·mol⁻¹ChemAxon
Polarizability37.62 ųChemAxon
Number of Rings4ChemAxon
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]+180.49931661259
DarkChem[M-H]-181.39531661259
DeepCCS[M-2H]-208.28330932474
DeepCCS[M+Na]+183.5130932474
AllCCS[M+H]+181.232859911
AllCCS[M+H-H2O]+178.132859911
AllCCS[M+NH4]+184.132859911
AllCCS[M+Na]+184.932859911
AllCCS[M-H]-189.332859911
AllCCS[M+Na-2H]-189.132859911
AllCCS[M+HCOO]-188.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-Isocorydine[H][C@@]12CC3=CC=C(OC)C(O)=C3C3=C(OC)C(OC)=CC(CCN1C)=C234301.2Standard polar33892256
(S)-Isocorydine[H][C@@]12CC3=CC=C(OC)C(O)=C3C3=C(OC)C(OC)=CC(CCN1C)=C232784.1Standard non polar33892256
(S)-Isocorydine[H][C@@]12CC3=CC=C(OC)C(O)=C3C3=C(OC)C(OC)=CC(CCN1C)=C232852.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-Isocorydine,1TMS,isomer #1COC1=CC=C2C[C@H]3C4=C(C=C(OC)C(OC)=C4C2=C1O[Si](C)(C)C)CCN3C2681.5Semi standard non polar33892256
(S)-Isocorydine,1TBDMS,isomer #1COC1=CC=C2C[C@H]3C4=C(C=C(OC)C(OC)=C4C2=C1O[Si](C)(C)C(C)(C)C)CCN3C2887.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Isocorydine GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ta-0069000000-0df9e0062a61b6f5b8992017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Isocorydine GC-MS (1 TMS) - 70eV, Positivesplash10-006t-1019000000-aa0786df5ba267f0e0e92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Isocorydine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Isocorydine 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 - (S)-Isocorydine LC-ESI-qTof , Positive-QTOFsplash10-00lj-1390000000-8648b87e5be5af57865d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine Linear Ion Trap , positive-QTOFsplash10-03di-0049000000-c3cd0bedd322f4365f672017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine Linear Ion Trap , positive-QTOFsplash10-0002-0009000000-510a4d7e28e894bf64232017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine , positive-QTOFsplash10-00lj-1390000000-8648b87e5be5af57865d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine 30V, Positive-QTOFsplash10-02a2-0090000000-9feb05710c9986e21d462021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine 50V, Positive-QTOFsplash10-054o-0980000000-898dbdc8c7ff49f386aa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine 50V, Positive-QTOFsplash10-05rc-0890000000-dc45a916bad1f29e719f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine 6V, Positive-QTOFsplash10-0006-0095000000-d95a1ec4e22d84ab1cf02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine 6V, Positive-QTOFsplash10-02a2-0090000000-73e62abe4ba1240a31002021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine 10V, Positive-QTOFsplash10-0006-0095000000-5cb39aed9d0bb14ea38a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine 6V, Positive-QTOFsplash10-0006-0095000000-a54974a771bb1b5fa4962021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine 6V, Positive-QTOFsplash10-02cb-0090000000-9294686f4de04327da732021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine 6V, Positive-QTOFsplash10-0006-0009000000-eb25fa2e3ca97a7ed87c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine 10V, Positive-QTOFsplash10-0006-0009000000-aac18fa03a624667c9112021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine 6V, Positive-QTOFsplash10-0006-0095000000-05e7cd025af07876a30f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine 6V, Positive-QTOFsplash10-02a2-0090000000-e7c46dbf270136f4ea542021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine 30V, Positive-QTOFsplash10-02a2-0090000000-455cfb312ea07df267fa2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine 10V, Positive-QTOFsplash10-0006-0096000000-f20f0a18703f41e3ac4a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Isocorydine 10V, Positive-QTOFsplash10-0006-0009000000-277b0f796e2f23a69cfc2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Isocorydine 10V, Positive-QTOFsplash10-0006-0009000000-26af6c94b94e28d921062016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Isocorydine 20V, Positive-QTOFsplash10-01ox-0049000000-8a99a90c6557e0c04fd12016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Isocorydine 40V, Positive-QTOFsplash10-0032-1091000000-2fa2513ead3fd70279122016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Isocorydine 10V, Negative-QTOFsplash10-0006-0009000000-d9089b3923b998a0fa982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Isocorydine 20V, Negative-QTOFsplash10-0006-0019000000-5821cc312129ea3c5a1c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Isocorydine 40V, Negative-QTOFsplash10-0006-0092000000-aab05b42a0932b71e3292016-08-03Wishart 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 IDFDB002000
KNApSAcK IDC00001872
Chemspider ID9737
KEGG Compound IDC09549
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10143
PDB IDNot Available
ChEBI ID561752
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.. .