Basic information
- CAS
35846-53-8- Standard SMILES
COc1cc2cc(c1Cl)N(C)C(=O)C[C@@H](OC(=O)[C@@H](C)N(C)C(C)=O)[C@]1(C)O[C@H]1[C@H](C)[C@@H]1C[C@@](O)(NC(=O)O1)[C@@H](OC)/C=C/C=C(\C)C2- InChIKey
WKPWGQKGSOKKOO-RJXPSCPHSA-N- Molecular formula
- C34H46ClN3O10
- Average molar mass
- 692.2 g/mol
- Monoisotopic mass
- 691.2871724
Names & identifiers
- Preferred name
- L-Alanine, N-acetyl-N-methyl-, 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-10,12,14(26),16,18-pentaen-6-yl ester, [1S-(1R*,2S*,3R*,5R*,6R*,16E,18E,20S*,21R*)]-
- IUPAC
- [(1S,2R,3S,5S,6R,16E,18E,20S,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-10,12,14(26),16,18-pentaen-6-yl] (2R)-2-[acetyl(methyl)amino]propanoate
- English name
- Maytansine
- Molecular formula
- C34H46ClN3O10
- Molecular weight
- 692.2
Names & synonyms
Ansa macrolideL-Alanine, N-acetyl-N-methyl-, 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-10,12,14(26),16,18-pentaen-6-yl ester, [1S-(1R*,2S*,3R*,5R*,6R*,16E,18E,20S*,21R*)]-(chloro-hydroxy-dimethoxy-tetramethyl-dioxo-[?]yl) (2R)-2-[acetyl(methyl)amino]propanoate4,24-Dioxa-9,22-diazatetracyclo[19.3.1.110,14.03,5]hexacosane, maytansine deriv.NSC 153858MaytansinemaitansineMaitansinaMaytansine, 10 mM in DMSOMicrotubule/Tubulin,tumor,mitotic,microtubule-targeted,arrest,Inhibitor,potent,subnanomolar,Maytansine,inhibit(14S,16S,32S,33S,2R,4S,10E,12E,14R)-86-Chloro-14-hydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-12,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl N-acetyl-N-methyl-L-alaninate(1S,2R,3S,5S,6R,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[19.3.1.11?,1?.03,?]hexacosa-10,12,14(26),16,18-pentaen-6-yl (2S)-2-(N-methylacetamido)propanoate
Properties
Computed structural properties
- XLogP
- 2
- Topological polar surface area
- 156 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 6
- Heavy atoms
- 48
- Formal charge
- 0
- Complexity
- 1,300
Physicochemical properties
- Melting point
- 183.5 · 183.5-184℃
- alpha
- 26 · D26 -145° (c = 0.055 in chloroform)
- Boiling point
- 895.1 · 895.1±65.0 °C(Predicted)
- Density
- 1.1049 · 1.1049 (rough estimate)
- refractive index
- 1.6 · 1.6000 (estimate)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- 1 mg/ml; · DMF: 1 mg/ml; DMSO: 10 mg/ml; Ethanol: 2 mg/ml; PBS (pH 7.2): insol
- form
- A solid
- pka
- 9.82 · 9.82±0.70(Predicted)
- color
- white to beige
- optical activity
- -14526 · -14526 (c 0.055, CHCl3)
- Stability
- Light Sensitive
- InChIKey
- WKPWGQKGSOKKOO-YHBUUTGONA-N
- SMILES
- O[C@]([C@@H](/C=C/C=C(CC1=CC2=C(C(OC)=C1)Cl)\C)OC)(C[C@H](O3)[C@H]([C@H]4[C@](C)([C@H](CC(N2C)=O)OC([C@@H](N(C)C(C)=O)C)=O)O4)C)NC3=O
- EWG's Food Scores
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
- wgk
- WGK 3
- Toxicity
- LD50 in rats (mg/kg): 0.48 s.c. (Mugera, Ward)
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H300+H310-H331
- Hazard Classifications
- Muta. 2Repr. 2STOT RE 1
- Precautionary statements
- P261-P262-P264-P270-P271-P280-P301+P310-P321-P330-P302+P352-P304+P340-P311-P361+P364-P403+P233-P405-P501
Chemistry & industry
Applications
DescriptionThis novel ansa macrolide alkaloid occurs in a number of May tan us species. The structure given has been elucidated from chemical and spectroscopic data. In low doses (25-50 mcg/kg), maytansine prolonged the survival of mice bearing vincristine-sensitive P388 leukemia but not those bearing vincristine-resistant tumour lines. In vitro, it suppressed the growth of U21 0, LSl78Y and P388 leukemia cells with ED50 of 2 X 10-9 , 1.5 X 10-9 and 6 X 10-10M respectively and elevated the mitotic index in L 121 0 cells. From labelling studies it was shown that the alkaloid inhibited DNA formation by P388 cells to a greater extent than RNA and protein synthesis. Maytensine did not inhibit RNA polymerase from Escherichia coli at levels as high as 1 X 10-4M.
UsesAntineoplastic.
Upstream & downstream products
Upstream raw materials
Related reactions
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Compound notes
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