CHEBI:17129 - (S)-scoulerine

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ChEBI Name (S)-scoulerine
ChEBI ID CHEBI:17129
ChEBI ASCII Name (S)-scoulerine
Definition A berberine alkaloid isolated from Corydalis saxicola.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:12413, CHEBI:442, CHEBI:18801, CHEBI:11071
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Formula C19H21NO4
Net Charge 0
Average Mass 327.37438
Monoisotopic Mass 327.147
InChI InChI=1S/C19H21NO4/c1-23-17-4-3-11-7-15-13-9-16(21)18(24-2)8-12(13)5-6-20(15)10-14(11)19(17)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1
InChIKey KNWVMRVOBAFFMH-HNNXBMFYSA-N
SMILES [H][C@@]12Cc3ccc(OC)c(O)c3CN1CCc1cc(OC)c(O)cc21
Metabolite of Species Details
Corydalis scouleri (IPNI:66415-2) See: PubMed
Corydalis cava (IPNI:672129-1) See: PubMed
Roles Classification
Biological Role(s): EC 5.99.1.2 (DNA topoisomerase) inhibitor
A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via alkaloid )
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ChEBI Ontology
Outgoing (S)-scoulerine (CHEBI:17129) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
(S)-scoulerine (CHEBI:17129) has role plant metabolite (CHEBI:76924)
(S)-scoulerine (CHEBI:17129) is a berberine alkaloid (CHEBI:22754)
(S)-scoulerine (CHEBI:17129) is a organic heterotetracyclic compound (CHEBI:38163)
Incoming cyclanoline (CHEBI:76923) has functional parent (S)-scoulerine (CHEBI:17129)
IUPAC Name
(13aS)-3,10-dimethoxy-5,8,13,13a-tetrahydro-6H-isoquino[3,2-a]isoquinoline-2,9-diol
Synonyms Sources
(−)-scoulerine ChEBI
(13aS)-5,8,13,13a-tetrahydro-3,10-dimethoxy-6H-dibenzo[a,g]quinolizine-2,9-diol KEGG COMPOUND
(S)-scoulerine ChEBI
(S)-Scoulerine KEGG COMPOUND
(S)-scoulerine UniProt
Manual Xrefs Databases
C00026092 KNApSAcK
C02106 KEGG COMPOUND
LSM-3391 LINCS
Scoulerine Wikipedia
SLX PDBeChem
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Registry Number Type Source
6451-73-6 CAS Registry Number KEGG COMPOUND
Citations Waiting for Citations Types Sources
18649321 PubMed citation Europe PMC
22029392 PubMed citation Europe PMC
Last Modified
25 February 2016