CHEBI:5373 - (S)-glaucine

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ChEBI Name (S)-glaucine
ChEBI ID CHEBI:5373
ChEBI ASCII Name (S)-glaucine
Definition An aporphine alkaloid that is (S)-1,2,9,10-tetrahydroxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline in which the four phenolic hydrogens have been replaced by methyl groups.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C21H25NO4
Net Charge 0
Average Mass 355.428
Monoisotopic Mass 355.178
InChI InChI=1S/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3/t15-/m0/s1
InChIKey RUZIUYOSRDWYQF-HNNXBMFYSA-N
SMILES C12=C3[C@](CC4=C1C=C(OC)C(=C4)OC)(N(CCC3=CC(=C2OC)OC)C)[H]
Metabolite of Species Details
Xylopia laevigata (IPNI:269802-2) Found in stem (BTO:0001300). See: PubMed
Corydalis turtschaninovii (NCBI:txid1577077) Found in tuber (BTO:0001400). See: PubMed
Corydalis turtschaninovii (NCBI:txid1577077) Found in rhizome (BTO:0001181). See: PubMed
Nandina domestica (NCBI:txid41776) Found in fruit (BTO:0000486). See: PubMed
Corydalis yanhusuo (NCBI:txid458692) See: PubMed
Glaucium flavum (NCBI:txid56853) Found in root (BTO:0001188). See: PubMed
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): NF-kappaB inhibitor
An inhibitor of NF-kappaB (nuclear factor kappa-light-chain-enhancer of activated B cells), a protein complex involved in the transcription of DNA.
antibacterial agent
A substance that kills or slows the growth of bacteria.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
rat metabolite
Any mammalian metabolite produced during a metabolic reaction in rat (Rattus norvegicus).
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
Application(s): platelet aggregation inhibitor
A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system.
antitussive
An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.
muscle relaxant
A drug used to produce muscle relaxation (excepting neuromuscular blocking agents). Its primary clinical and therapeutic use is the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. Also used for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in multiple sclerosis.
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (S)-glaucine (CHEBI:5373) has role antibacterial agent (CHEBI:33282)
(S)-glaucine (CHEBI:5373) has role antineoplastic agent (CHEBI:35610)
(S)-glaucine (CHEBI:5373) has role antitussive (CHEBI:51177)
(S)-glaucine (CHEBI:5373) has role muscle relaxant (CHEBI:51371)
(S)-glaucine (CHEBI:5373) has role NF-κB inhibitor (CHEBI:73240)
(S)-glaucine (CHEBI:5373) has role plant metabolite (CHEBI:76924)
(S)-glaucine (CHEBI:5373) has role platelet aggregation inhibitor (CHEBI:50427)
(S)-glaucine (CHEBI:5373) has role rat metabolite (CHEBI:86264)
(S)-glaucine (CHEBI:5373) is a aporphine alkaloid (CHEBI:134209)
(S)-glaucine (CHEBI:5373) is a organic heterotetracyclic compound (CHEBI:38163)
(S)-glaucine (CHEBI:5373) is a polyether (CHEBI:46774)
(S)-glaucine (CHEBI:5373) is a tertiary amino compound (CHEBI:50996)
(S)-glaucine (CHEBI:5373) is conjugate base of (S)-glaucine(1+) (CHEBI:134212)
Incoming (S)-1,2,9,10-tetramethoxy-6-methylaporphine(1+) (CHEBI:134213) has functional parent (S)-glaucine (CHEBI:5373)
(S)-glaucine(1+) (CHEBI:134212) is conjugate acid of (S)-glaucine (CHEBI:5373)
IUPAC Name
(6aS)-1,2,9,10-tetramethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline
Synonyms Sources
1,2,9,10-Tetramethoxy-6a-alpha-aporphine ChemIDplus
Boldine dimethyl ether ChemIDplus
d-Glaucine ChemIDplus
Glaucine KEGG COMPOUND
S-(+)-Glaucine ChemIDplus
Manual Xrefs Databases
C00001861 KNApSAcK
C09446 KEGG COMPOUND
D08014 KEGG DRUG
View more database links
Registry Numbers Types Sources
475-81-0 CAS Registry Number KEGG COMPOUND
475-81-0 CAS Registry Number ChemIDplus
95206 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
23194502 PubMed citation Europe PMC
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Last Modified
06 April 2017