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Record Information
Version2.0
Created at2022-09-02 23:59:05 UTC
Updated at2022-09-02 23:59:05 UTC
NP-MRD IDNP0164987
Secondary Accession NumbersNone
Natural Product Identification
Common Name(r)-stylopine
DescriptionL-Tetrahydrocoptisine, also known as stylopin, belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton. (r)-stylopine is found in Corydalis intermedia, Corydalis saxicola and Fumaria vaillantii. (r)-stylopine was first documented in 1989 (PMID: 2576175). Based on a literature review very few articles have been published on l-Tetrahydrocoptisine (PMID: 7515744).
Structure
Thumb
Synonyms
ValueSource
(12BS)-6,7,12b,13-Tetrahydro-4H-bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizineMeSH
6,7,12b,13-Tetrahydro-4H-bis(1,3)benzodioxolo(5,6-a:4',5'-g)quinolizineMeSH
StylopinMeSH
Stylopine, (S)-isomerMeSH
(-)-StylopineMeSH
Stylopine, 14C-labeled, (+,-)-isomerMeSH
(+-)-TetrahydrocoptisineMeSH
(S)-StylopineMeSH
(+-)StylopineMeSH
(-)-TetrahydrocoptisineMeSH
StylopineMeSH
TetrahydrocoptisineMeSH
Chemical FormulaC19H17NO4
Average Mass323.3480 Da
Monoisotopic Mass323.11576 Da
IUPAC Name(1R)-5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{15,23}.0^{16,20}]tetracosa-2(10),3,8,15(23),16(20),21-hexaene
Traditional Name(1R)-5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.0^{2,10}.0^{4,8}.0^{15,23}.0^{16,20}]tetracosa-2(10),3,8,15(23),16(20),21-hexaene
CAS Registry NumberNot Available
SMILES
C1OC2=C(O1)C=C1[C@H]3CC4=C(CN3CCC1=C2)C1=C(OCO1)C=C4
InChI Identifier
InChI=1S/C19H17NO4/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14/h1-2,6-7,15H,3-5,8-10H2/t15-/m1/s1
InChI KeyUXYJCYXWJGAKQY-OAHLLOKOSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Corydalis intermediaLOTUS Database
Corydalis saxicolaLOTUS Database
Fumaria vaillantiiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassProtoberberine alkaloids and derivatives
Sub ClassNot Available
Direct ParentProtoberberine alkaloids and derivatives
Alternative Parents
Substituents
  • Protoberberine skeleton
  • Tetrahydroprotoberberine skeleton
  • Tetrahydroisoquinoline
  • Benzodioxole
  • Aralkylamine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Acetal
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.36ALOGPS
logP3.03ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)5.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.16 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity87.04 m³·mol⁻¹ChemAxon
Polarizability35.02 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00026095
Chemspider ID607731
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTetrahydrocoptisine
METLIN IDNot Available
PubChem Compound697545
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Kubo M, Matsuda H, Tokuoka K, Ma S, Shiomoto H: Anti-inflammatory activities of methanolic extract and alkaloidal components from Corydalis tuber. Biol Pharm Bull. 1994 Feb;17(2):262-5. doi: 10.1248/bpb.17.262. [PubMed:7515744 ]
  2. Liu GQ, Han BY, Wang EH: [Blocking actions of l-stephanine, xylopine and 7 other tetrahydroisoquinoline alkaloids on alpha adrenoceptors]. Zhongguo Yao Li Xue Bao. 1989 Jul;10(4):302-6. [PubMed:2576175 ]
  3. LOTUS database [Link]