Ansamitocin P-3 - ≥95% , CAS No.66547-09-9

CAS: 66547-09-9 Cat. No.: A274869 Molecular Weight: 635.14 EC Number: 636-289-0

GRADE & PURITY ≥95%

Synonyms

[(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-10,12,14(26),16,18-pentaen-6-yl] butanoate | Maytansine, O(sup 3)-de(2-(acetylmethylamino)-1

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Store at -20°C. Store under desiccating conditions. The product can be stored for up to 12 months.

Specifications

Synonyms

[(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, 12, 14(26), 16, 18-pentaen-6-yl] butanoate | Maytansine, O(sup 3)-de(2-(acetylmethylamino)-1

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

Potent microtubule depolymerizing agent. Binds to tubulin at the vinblastine site. Induces p53-mediated apoptosis. Shows cytotoxic effects to tumor cell lines. Maytansine analog. Shows antitumor effects in vivo. Orally active.

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥95%

Names and Identifiers

• Canonical Smiles: CCCC(=O)OC1CC(=O)N(C2=C(C(=CC(=C2)CC(=CC=CC(C3(CC(C(C4C1(O4)C)C)OC(=O)N3)O)OC)C)OC)Cl)C
• IUPAC Name: [(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-10,12,14(26),16,18-pentaen-6-yl] butanoate
• InChIKey: WLKHTIAFMSHJLG-BYXOJEECSA-N
• INCHI: 1S/C32H43ClN2O9/c1-8-10-27(37)43-25-16-26(36)35(5)21-14-20(15-22(40-6)28(21)33)13-18(2)11-9-12-24(41-7)32(39)17-23(42-30(38)34-32)19(3)29-31(25,4)44-29/h9,11-12,14-15,19,23-25,29,39H,8,10,13,16-17H2,1-7H3,(H,34,38)/b12-9+,18-11+/t19-,23+,24-,25+,29+,31+,32+/m1/s1
• Isomeric SMILES: CCCC(=O)O[C@H]1CC(=O)N(C2=C(C(=CC(=C2)C/C(=C/C=C/[C@H]([C@]3(C[C@@H]([C@H]([C@H]4[C@]1(O4)C)C)OC(=O)N3)O)OC)/C)OC)Cl)C
• Molecular Weight: 635.14
• Reaxy-Rn: 38875189
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=38875189&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Macrolactams

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Macrolactams
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Macrolactams
• Alternative Parents: Anisoles Alkyl aryl ethers Fatty acid esters 1,3-oxazinanes Aryl chlorides Tertiary carboxylic acid amides Carbamate esters Lactams Carboxylic acid esters Dialkyl ethers Alkanolamines Oxacyclic compounds Azacyclic compounds Monocarboxylic acids and derivatives Epoxides Carbonyl compounds Organic oxides Organochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Macrolactam - Anisole - Phenol ether - Alkyl aryl ether - Fatty acid ester - 1,3-oxazinane - Aryl chloride - Aryl halide - Fatty acyl - Benzenoid - Oxazinane - Carbamic acid ester - Tertiary carboxylic acid amide - Carboxamide group - Carboxylic acid ester - Lactam - Oxacycle - Carboxylic acid derivative - Alkanolamine - Dialkyl ether - Oxirane - Ether - Azacycle - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Organonitrogen compound - Organochloride - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organic oxygen compound - Carbonyl group - Organic nitrogen compound - Organohalogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in DMSO
• Molecular Weight: 635.100 g/mol
• XLogP3: 2.900
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 6
• Exact Mass: 634.266 Da
• Monoisotopic Mass: 634.266 Da
• Topological Polar Surface Area: 136.000 Ų
• Heavy Atom Count: 44
• Formal Charge: 0
• Complexity: 1130.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 7
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1