CHEBI:4393 - (−)-demecolcine

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ChEBI Name (−)-demecolcine
ChEBI ID CHEBI:4393
ChEBI ASCII Name (-)-demecolcine
Definition A secondary amino compound that is (S)-colchicine in which the N-acetyl group is replaced by an N-methyl group. Isolable from the autumn crocus, Colchicum autumnale, it is less toxic than colchicine and is used as an antineoplastic.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C21H25NO5
Net Charge 0
Average Mass 371.42690
Monoisotopic Mass 371.173
InChI InChI=1S/C21H25NO5/c1-22-15-8-6-12-10-18(25-3)20(26-4)21(27-5)19(12)13-7-9-17(24-2)16(23)11-14(13)15/h7,9-11,15,22H,6,8H2,1-5H3/t15-/m0/s1
InChIKey NNJPGOLRFBJNIW-HNNXBMFYSA-N
SMILES CN[C@H]1CCc2cc(OC)c(OC)c(OC)c2-c2ccc(OC)c(=O)cc12
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): microtubule-destabilising agent
Any substance that interacts with tubulin to inhibit polymerisation of microtubules.
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): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (−)-demecolcine (CHEBI:4393) has role antineoplastic agent (CHEBI:35610)
(−)-demecolcine (CHEBI:4393) has role microtubule-destabilising agent (CHEBI:61951)
(−)-demecolcine (CHEBI:4393) is a alkaloid (CHEBI:22315)
(−)-demecolcine (CHEBI:4393) is a secondary amino compound (CHEBI:50995)
IUPAC Name
(7S)-1,2,3,10-tetramethoxy-7-(methylamino)-6,7-dihydrobenzo[a]heptalen-9(5H)-one
INNs Sources
demecolcina ChemIDplus
demecolcine ChemIDplus
demecolcinum ChemIDplus
Synonyms Sources
(−)-colchamine ChemIDplus
Colcemid KEGG COMPOUND
N-deacetyl-N-methylcolchicine ChemIDplus
N-desacetyl-N-methylcolchicine ChemIDplus
N-methyl-N-deacetylcolchicine ChemIDplus
N-methyl-N-desacetylcolchicine ChemIDplus
Reichstein's F ChemIDplus
Santavy's substance F ChemIDplus
Manual Xrefs Databases
4375 DrugCentral
C00027138 KNApSAcK
C11250 KEGG COMPOUND
DE936268 Patent
Demecolcine Wikipedia
LSM-6590 LINCS
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Registry Numbers Types Sources
2822892 Reaxys Registry Number Reaxys
477-30-5 CAS Registry Number KEGG COMPOUND
477-30-5 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
1061646 PubMed citation Europe PMC
20082301 PubMed citation Europe PMC
22394737 PubMed citation Europe PMC
2329167 PubMed citation Europe PMC
2977921 PubMed citation Europe PMC
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7720099 PubMed citation Europe PMC
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Last Modified
22 February 2017