Geldanamycin from Streptomyces hygroscopicus - Moligand™, ≥98%(HPLC) , Inhibitor of heat shock protein 90 alpha family class B member 1, CAS No.30562-34-6, Inhibitor of heat shock protein 90 alpha family class B member 1

CAS: 30562-34-6 Cat. No.: G102383 Molecular Weight: 560.64 EC Number: 805-356-8

GRADE & PURITY Moligand™, ≥98%(HPLC)

Synonyms

[(3R,5S,6R,7S,8E,10S,11S,12Z,14E)-6-hydroxy-5,11,21-trimethoxy-3,7,9,15-tetramethyl-16,20,22-trioxo-17-azabicyclo[16.3.1]docosa-1(21),8,12,14,18-pentaen-10-yl] carbamate | CCG-208040 | HMS1362E15 | [(3S,5S,6R,7S,8E,10R,11S,12Z,14E)-6-Hydroxy-5,11,21-trime

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

λmax 305(MeOH)(Lit.) A benzoquinoid antibiotic that inhibits p60c-src tyrosine kinase and c-myc gene expression in murine lymphoblastoma cells. Geldanamycin has antiproliferative and antitumor effects. Rapidly depletes p185c-erbB2 protein tyrosine kinase in breast carcinoma cells. Binds to HSP90 and disrupts Raf1-HSP90 complex leading to destabilization of Raf1. Inhibits basal and hypoxia-induced expression of c-Jun (IC50 = 75 nM) and abolishes hypoxia-induced increase in c-Jun N-terminal kinase activity. Also known to selectively destabilize mutated p53 protein from a number of breast, leukemia, and prostate cell lines. A benzoquinoid antibiotic that is a potent inhibitor of pp60src tyrosine kinase. Geldanamycin has antiproliferative and antitumor effects. Inhibits basal and hypoxia-induced expression of c-Jun (IC50 = 75 nM) and abolishes hypoxia-induced increase in c-Jun N-terminal Kinase activity. Binds to HSP90 and disrupts raf1-HSP90 complex leading to destabilizing of Raf1. Also destabilizes mutant p53 protein from a number of breast, leukemic, and prostate cell lines. Inhibits c-myc expression in murine lymphoblastoma cells. Approximately ten-fold more potent than herbimycin A

Specifications

Synonyms

[(3R, 5S, 6R, 7S, 8E, 10S, 11S, 12Z, 14E)-6-hydroxy-5, 11, 21-trimethoxy-3, 7, 9, 15-tetramethyl-16, 20, 22-trioxo-17-azabicyclo[16.3.1]docosa-1(21), 8, 12, 14, 18-pentaen-10-yl] carbamate | CCG-208040 | HMS1362E15 | [(3S, 5S, 6R, 7S, 8E, 10R, 11S, 12Z, 14E)-6-Hydroxy-5, 11, 21-trime

Specifications & Purity

Moligand™, ≥98%(HPLC)

Biochemical and Physiological Mechanisms

Potent fluorescent labelled-HSP90 inhibitor for in vitro and in vivo use. Geldanamycin from Streptomyces hygroscopicus .

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 B member 1

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

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 504763516
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763516
• Canonical Smiles: CC1CC(C(C(C=C(C(C(C=CC=C(C(=O)NC2=CC(=O)C(=C(C1)C2=O)OC)C)OC)OC(=O)N)C)C)O)OC
• IUPAC Name: [(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-8,14,19-trimethoxy-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: QTQAWLPCGQOSGP-KSRBKZBZSA-N
• INCHI: 1S/C29H40N2O9/c1-15-11-19-25(34)20(14-21(32)27(19)39-7)31-28(35)16(2)9-8-10-22(37-5)26(40-29(30)36)18(4)13-17(3)24(33)23(12-15)38-6/h8-10,13-15,17,22-24,26,33H,11-12H2,1-7H3,(H2,30,36)(H,31,35)/b10-8-,16-9+,18-13+/t15-,17+,22+,23+,24-,26+/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)OC)/C)OC)OC(=O)N)\C)C)O)OC
• WGK Germany: 2
• RTECS: LX8920000
• Alternate CAS: 30562-34-6
• MeSH Entry Terms: geldanamycin;geldanomycin
• Molecular Weight: 560.64
• Reaxy-Rn: 26145919
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=26145919&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 esters Vinylogous amides Carbamate esters Secondary carboxylic acid amides Secondary alcohols Organic carbonic acids and derivatives Lactams Cyclic ketones Dialkyl ethers Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: Macrolactam - Vinylogous ester - Vinylogous amide - Carbamic acid ester - Carboxamide group - Ketone - Lactam - Carbonic acid derivative - Secondary alcohol - Secondary carboxylic acid amide - Cyclic ketone - Carboxylic acid derivative - Dialkyl ether - Ether - Azacycle - Organoheterocyclic compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Carbonyl group - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Organic nitrogen 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: Ansamycins

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)

TRAP1 Tchem Heat shock protein 75 kDa, mitochondrial (1 Activities)

Discover Target: TRAP1

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

HSP90AA1 Tchem Heat shock protein HSP 90-alpha (20 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 (8 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 dimethyl sulfoxide at 100 mg/mL.
• Sensitivity: heat sensitive
• Melt Point(°C): 255°C
• Molecular Weight: 560.600 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 560.273 Da
• Monoisotopic Mass: 560.273 Da
• Topological Polar Surface Area: 163.000 Ų
• Heavy Atom Count: 40
• Formal Charge: 0
• Complexity: 1150.000
• 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. Xu Yao, Jie Zhu, Lin Li, Bo Yang, Bixia Chen, Endong Bao, Xiaohui Zhang.  (2023)  Hsp90 protected chicken primary myocardial cells from heat-stress injury by inhibiting oxidative stress and calcium overload in mitochondria.  BIOCHEMICAL PHARMACOLOGY,      [PMID:36708886] [10.1016/j.bcp.2023.115434]

2. Yuanyuan Zhu, Yanyan Huang, Tian-Hao Yan, Jialuo Li, Yongming Li, Hannah F. Drake, Huifei Zhong, Yulong Jin, Rui Zhao, Hong-Cai Zhou.  (2022)  Metal-Organic Framework-Based Nanoheater with Photo-Triggered Cascade Effects for On-Demand Suppression of Cellular Thermoresistance and Synergistic Cancer Therapy.  Advanced Healthcare Materials,  11  (13): (2200004).  [PMID:35306753] [10.1002/adhm.202200004]