CHEBI:82755 - mertansine

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ChEBI Name mertansine
ChEBI ID CHEBI:82755
Definition An organic heterotetracyclic compound and 19-membered macrocyclic lactam that is maytansine in which one of the hydrogens of the terminal N-acetyl group is replaced by a sulfanylmethyl group.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C35H48ClN3O10S
Net Charge 0
Average Mass 738.28800
Monoisotopic Mass 737.275
InChI InChI=1S/C35H48ClN3O10S/c1-19-10-9-11-26(46-8)35(44)18-25(47-33(43)37-35)20(2)31-34(4,49-31)27(48-32(42)21(3)38(5)28(40)12-13-50)17-29(41)39(6)23-15-22(14-19)16-24(45-7)30(23)36/h9-11,15-16,20-21,25-27,31,44,50H,12-14,17-18H2,1-8H3,(H,37,43)/b11-9+,19-10+/t20-,21+,25+,26-,27+,31+,34+,35+/m1/s1
InChIKey ANZJBCHSOXCCRQ-FKUXLPTCSA-N
SMILES CO[C@@H]1\C=C\C=C(C)\Cc2cc(OC)c(Cl)c(c2)N(C)C(=O)C[C@H](OC(=O)[C@H](C)N(C)C(=O)CCS)[C@]2(C)O[C@H]2[C@H](C)[C@@H]2C[C@@]1(O)NC(=O)O2
Roles Classification
Biological Role(s): tubulin modulator
Any substance that interacts with tubulin to inhibit or promote polymerisation of microtubules.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing mertansine (CHEBI:82755) has functional parent maytansine (CHEBI:6701)
mertansine (CHEBI:82755) has role antineoplastic agent (CHEBI:35610)
mertansine (CHEBI:82755) has role tubulin modulator (CHEBI:60832)
mertansine (CHEBI:82755) is a α-amino acid ester (CHEBI:46874)
mertansine (CHEBI:82755) is a carbamate ester (CHEBI:23003)
mertansine (CHEBI:82755) is a epoxide (CHEBI:32955)
mertansine (CHEBI:82755) is a maytansinoid (CHEBI:82760)
mertansine (CHEBI:82755) is a organic heterotetracyclic compound (CHEBI:38163)
mertansine (CHEBI:82755) is a organochlorine compound (CHEBI:36683)
mertansine (CHEBI:82755) is a thiol (CHEBI:29256)
Synonyms Sources
(1S,2R,3S,5S,6S,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosa-10(26),11,13,16,18-pentaen-6-yl (2S)-2-[methyl(3-sulfanylpropanoyl)amino]propanoate IUPAC
DM 1 ChemIDplus
DM1 ChemIDplus
maytansinoid DM 1 ChemIDplus
maytansinoid DM1 ChEBI
N2'-deacetyl-N2'-(3-mercapto-1-oxopropyl)-maytansine ChEBI
Database Links Databases
C20259 KEGG COMPOUND
Mertansine Wikipedia
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Registry Numbers Types Sources
10753281 Reaxys Registry Number Reaxys
139504-50-0 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
23798344 PubMed citation Europe PMC
24389179 PubMed citation Europe PMC
24623670 PubMed citation Europe PMC
24887180 PubMed citation Europe PMC
Last Modified
09 January 2015