Alvespimycin - Moligand™, ≥98% , Inhibitor of heat shock protein 90 alpha family class A member 1, CAS No.467214-20-6, Inhibitor of heat shock protein 90 alpha family class A member 1

CAS: 467214-20-6 Cat. No.: A125535 Molecular Weight: 616.75 EC Number: 154-807-9

GRADE & PURITY Moligand™, ≥98%

Synonyms

NSC 707545 | (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-{[2-(dimethylamino)ethyl]amino}-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate | 17-DMAG | ((4E,6Z,8S,9S,10E,12S,13R,14S,1

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

A synthetic Geldanamycin derivative and inhibitor of Hsp90.

Specifications

Synonyms

NSC 707545 | (4E, 6Z, 8S, 9S, 10E, 12S, 13R, 14S, 16R)-19-{[2-(dimethylamino)ethyl]amino}-13-hydroxy-8, 14-dimethoxy-4, 10, 12, 16-tetramethyl-3, 20, 22-trioxo-2-azabicyclo[16.3.1]docosa-1(21), 4, 6, 10, 18-pentaen-9-yl carbamate | 17-DMAG | ((4E, 6Z, 8S, 9S, 10E, 12S, 13R, 14S, 1

Specifications & Purity

Moligand™, ≥98%

Biochemical and Physiological Mechanisms

17-DMAG, 17-dimethylaminoethylamino-17-demethoxygeldanamycin, is a synthetic derivative of the antibiotic Geldanamycin with lower hepatotoxicity than the parent antibiotic and higher potency and availability than the similar derivative 17-AAG .17-DMAG is

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of heat shock protein 90 alpha family class A member 1

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C(=C(C1)C2=O)NCCN(C)C)C)OC)OC(=O)N)C)C)O)OC
• IUPAC Name: [(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-[2-(dimethylamino)ethylamino]-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl] carbamate
• InChIKey: KUFRQPKVAWMTJO-LMZWQJSESA-N
• INCHI: 1S/C32H48N4O8/c1-18-14-22-27(34-12-13-36(5)6)24(37)17-23(29(22)39)35-31(40)19(2)10-9-11-25(42-7)30(44-32(33)41)21(4)16-20(3)28(38)26(15-18)43-8/h9-11,16-18,20,25-26,28,30,34,38H,12-15H2,1-8H3,(H2,33,41)(H,35,40)/b11-9-,19-10+,21-16+/t18-,20+,25+,26+,28-,30+/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)NCCN(C)C)/C)OC)OC(=O)N)\C)C)O)OC
• Alternate CAS: 467214-20-6
• MeSH Entry Terms: 17-(dimethylaminoethylamino)-17-demethoxy-geldanamycin;17-(dimethylaminoethylamino)-17-demethoxygeldanamycin;17-desmethoxy-17-n,n-dimethylaminoethylamino-geldanamycin;17-dimethylaminoethylamino-17-demethoxy-geldanamycin;17-DMAG;17DMAG;alvespimycin;KOS 102
• Molecular Weight: 616.75
• Reaxy-Rn: 25845674
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25845674&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 Trialkylamines 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 - Tertiary aliphatic amine - Tertiary amine - 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: tertiary amino compound - 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 (6 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 (4 Activities)

Discover Target: HSP90AB1

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

HIF1A Tchem Hypoxia-inducible factor 1-alpha (2 Activities)

Discover Target: HIF1A

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

Chemical and Physical Properties

• Solubility: Soluble in water, ethanol (10 mg/mL), and DMSO (>25 mg/mL).
• Molecular Weight: 616.700 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 616.347 Da
• Monoisotopic Mass: 616.347 Da
• Topological Polar Surface Area: 170.000 Ų
• Heavy Atom Count: 44
• Formal Charge: 0
• Complexity: 1230.000
• 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

References

1. Li Peng, Bai Chujie, Zhan Lingmin, Zhang Haoran, Zhang Yuanyuan, Zhang Wuxia, Wang Yingdong, Zhao Jinzhong.  (2023)  Specific gene module pair-based target identification and drug discovery.  Frontiers in Pharmacology,      [PMID:36726786] [10.3389/fphar.2022.1089217]