17-AAG - ≥98% , CAS No.75747-14-7

CAS: 75747-14-7 Cat. No.: A126970 Formula: C₃₁H₄₃N₃O₈ Molecular Weight: 585.69

GRADE & PURITY ≥98%

Synonyms

Allylamino-17-demethoxygeldanamycin, 17-|CNF-1010|17-(Allylamino) Geldanamycin|KOS 953|Tanespimycin (17-AAG)|17AAG|17-AAG|17-Demethoxy-17-allylamino geldanamycin|Cp 127374|Tanespimycin|17-demethoxy-17-(2-propenylamino)-|Geldanamycin

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

17-AAG (Tanespimycin) is a potent HSP90 inhibitor with IC50 of 5 nM, having a 100-fold higher binding affinity for HSP90 derived from tumour cells than HSP90 from normal cells.
A potent Hsp90 inhibitor for tumor cells

Specifications

Synonyms

Allylamino-17-demethoxygeldanamycin, 17- | CNF-1010 | 17-(Allylamino) Geldanamycin | KOS 953 | Tanespimycin (17-AAG) | 17AAG | 17-AAG | 17-Demethoxy-17-allylamino geldanamycin | Cp 127374 | Tanespimycin | 17-demethoxy-17-(2-propenylamino)- | Geldanamycin

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

17-AAG is a less toxic and more stable analog of geldanamycin. It acts an Hsp90 inhibitor that displays a 100-fold higher affinity for Hsp90 derived from tumor cells compared to Hsp90 from normal cells. 17-AAG inhibits Akt1 (Akt) activation and expression

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

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

Action Type

INHIBITOR

Note

Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

Pubchem Sid

504764267

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504764267

Canonical Smiles

CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C(=C(C1)C2=O)NCC=C)C)OC)OC(=O)N)C)C)O)OC

IUPAC Name

[(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-19-(prop-2-enylamino)-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate

InChIKey

AYUNIORJHRXIBJ-TXHRRWQRSA-N

INCHI

1S/C31H43N3O8/c1-8-12-33-26-21-13-17(2)14-25(41-7)27(36)19(4)15-20(5)29(42-31(32)39)24(40-6)11-9-10-18(3)30(38)34-22(28(21)37)16-23(26)35/h8-11,15-17,19,24-25,27,29,33,36H,1,12-14H2,2-7H3,(H2,32,39)(H,34,38)/b11-9-,18-10+,20-15+/t17-,19+,24+,25+,27-,29+/m1/s1

Isomeric SMILES

C[C@H]1C[C@@H]([C@@H]([C@H](/C=C(/[C@@H]([C@H](/C=C\C=C(\C(=O)NC2=CC(=O)C(=C(C1)C2=O)NCC=C)/C)OC)OC(=O)N)\C)C)O)OC

WGK Germany

3

Molecular Weight

585.69

Reaxy-Rn

29616581

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=29616581&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: Vinylogous amides Carbamate esters Secondary carboxylic acid amides Secondary alcohols Organic carbonic acids and derivatives Lactams Cyclic ketones Enamines Dialkylamines Dialkyl ethers Azacyclic compounds Organopnictogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Macrolactam - Vinylogous amide - Carbamic acid ester - Amino acid or derivatives - Carboxamide group - Ketone - Lactam - Carbonic acid derivative - Secondary alcohol - Cyclic ketone - Secondary carboxylic acid amide - Carboxylic acid derivative - Dialkyl ether - Secondary aliphatic amine - Enamine - Ether - Azacycle - Organoheterocyclic compound - Secondary amine - Carbonyl group - Organic nitrogen compound - Amine - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Alcohol - Aliphatic 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: secondary amino compound - lactam - macrocycle - benzoquinones

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

Associated Targets(Human)

HSP90AA1 Tchem Heat shock protein HSP 90-alpha (24 Activities)

Discover Target: HSP90AA1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

HSP90AB1 Tchem Heat shock protein HSP 90-beta (11 Activities)

Discover Target: HSP90AB1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Chemical and Physical Properties

• Solubility: Soluble in DMSO (≥20 mg/ml at 25 °C), methanol (10 mg/ml), chloroform (10 mg/ml yielding a clear purple solution), water (<1 mg/ml at 25 °C), and ethanol (≥5 mg/ml at 25 °C).
• Sensitivity: Light sensitive
• Molecular Weight: 585.700 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 585.305 Da
• Monoisotopic Mass: 585.305 Da
• Topological Polar Surface Area: 166.000 Ų
• Heavy Atom Count: 42
• Formal Charge: 0
• Complexity: 1210.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 6
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 3
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 3
• Covalently-Bonded Unit Count: 1