(S)-Canadine

HCID 21171

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Basic information

CAS: 5096-57-1
Standard SMILES: COc1ccc2c(c1OC)CN1CCc3cc4c(cc3[C@@H]1C2)OCO4
InChIKey: VZTUIEROBZXUFA-INIZCTEOSA-N
Molecular formula: C20H21NO4
Average molar mass: 339.4 g/mol
Monoisotopic mass: 339.14705815

Overview

(S)-canadine is the (S)-enantiomer of canadine. It has a role as a plant metabolite. It is an an (S)-7,8,13,14-tetrahydroprotoberberine and a canadine. It is functionally related to a (S)-nandinine. It is an enantiomer of a (R)-canadine.

Names & identifiers

Preferred name: (S)-Canadine
IUPAC: (1S)-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaene
English name: canadine
Molecular formula: C20H21NO4
Molecular weight: 339.39

Names & synonyms

5096-57-1(S)-Canadine(S)-TetrahydroberberineCHEBI:16592(1S)-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaene(13aS)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine(13aS)-9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-[1,3]dioxolo[4,5-g]isoquino[3,2-a]isoquinoline(13aS)-5,8,13,13a-Tetrahydro-9,10-dimethoxy-6H-Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizine(13aS)-9,10-dimethoxy-5,8,13,13a-tetrahydro-6H-(1,3)dioxolo(4,5-g)isoquino(3,2-a)isoquinoline(1S)-16,17-dimethoxy-5,7-dioxa-13-azapentacyclo(11.8.0.02,10.04,8.015,20)henicosa-2,4(8),9,15(20),16,18-hexaeneRefChem:1051175Canadine l-form

Show more names

C033296H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizine, 5,8,13,13a-tetrahydro-9,10-dimethoxy-, (13aS)-

(-)-Canadine(-)-Tetrahydroberberine(S)-(-)-Canadine(S)-(-)-TetrahydroberberineQ97V5BUT9DNSC 36351alpha-canadineCanadine, (-)-

Database identifiers

CAS: 5096-57-1
PubChem CID: 21171
DTXSID: DTXSID10110003
ChEMBL: CHEMBL490533
ChEBI: CHEBI:16592
UNII: Q97V5BUT9D
EC Number: 225-815-0
Nikkaji: J71.178K

Properties

Computed structural properties

XLogP: 3.1
Topological polar surface area: 40.2 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 5
Rotatable bonds: 2
Heavy atoms: 25
Formal charge: 0
Complexity: 488

Physicochemical properties

Melting point: 135 ° · 135°
alpha: 22 · D22 -308°; -317° (c = 0.28; 0.4, both in methanol)
Boiling point: 475.36 °C · 475.36°C (rough estimate)
Density: 1.227 · 1.2270 (rough estimate)
refractive index: 1.6 · 1.6000 (estimate)
storage temp.: Refrigerator
solubility: Chloroform, Ethyl Acetate (Slightly), Methanol (Very Slightly, Heated)
form: Solid
pka: 6.53 · 6.53±0.20(Predicted)
color: Pale Yellow to Light Yellow
FDA UNII: 97 V5BUT9D · Q97V5BUT9D
RIDADR: 1544 · 1544
HazardClass: 6.1 · 6.1(b)
PackingGroup: III

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

ridadr: 1544
hazard_class: 6.1(b)
packing_group: III

Chemistry & industry

Applications · 1 item

Uses(S)-(-)-Canadine is a protoberberine alkaloid which potently block functional KATP channels natively expressed on midbrain dopamine neurons. Canadine is used for treatment of degenerative diseases or conditions associated with KATP channel signaling. (S)-(-)-Canadine has a strong central nervous system-depressing activity and is used in the preparation of tetrahydroprotoberberine derivatives as new antipsychotic agents.

Suppliers47 total

武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]

上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]

安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]

上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]

成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]

Additional notes

DefinitionChEBI: (S)-canadine is the (S)-enantiomer of canadine. It has a role as a plant metabolite. It is functionally related to a (S)-nandinine. It is an enantiomer of a (R)-canadine.

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