CAS 30562-34-6|Geldanamycin

Introduction：Basic information about CAS 30562-34-6|Geldanamycin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Geldanamycin BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
MUTATION DATA
5. Safety Information
6. Customs
7. Articles12
8. Synonyms

Common Name	Geldanamycin
CAS Number	30562-34-6	Molecular Weight	560.636
Density	1.2±0.1 g/cm3	Boiling Point	783.9±60.0 °C at 760 mmHg
Molecular Formula	C₂₉H₄₀N₂O₉	Melting Point	255 °C
MSDS	ChineseUSA	Flash Point	427.9±32.9 °C

Names

Name	geldanamycin
Synonym	More Synonyms

Geldanamycin BiologicalActivity

Description	Geldanamycin is a Hsp90 inhibitor with antimicrobial activity against many Gram-positive and some Gram-negative bacteria.
Related Catalog	Signaling Pathways >>Cell Cycle/DNA Damage >>HSPSignaling Pathways >>Metabolic Enzyme/Protease >>HSPResearch Areas >>CancerNatural Products >>Others
Target	HSP90:1.2 μM (Kd)
In Vitro	Geldanamycin significantly delays and reduces viperin expression, indicating that IRF3 is involved in viperin induction in RAW264.7 cells[1]. Geldanamycin (GA), a benzoquinone ansamycin, protected against neuronal injury induced by oxygen-glucose deprivation (OGD)/zVAD treatment in cultured primary neurons. More importantly, Geldanamycin decreases RIP1 protein level in a time and concentration-dependent manner. Geldanamycin also decreases the Hsp90 protein level, which causes instability of RIP1 protein, resulting in decreased RIP1 protein level but not RIP1 mRNA level after Geldanamycin treatment[2]. Geldanamycin (GA) is identified as the first natural product inhibitor of Hsp90 that binds to the N-terminal ATPase domain of Hsp90 to inhibit its chaperone function, and significantly induces tumor cell death via an apoptotic mechanism[3].
References	[1]. Tang HB, et al. Viperin inhibits rabies virus replication via reduced cholesterol and sphingomyelin and is regulated upstream by TLR4. Sci Rep. 2016 Jul 26;6:30529 [2]. Chen WW, et al. RIP1 mediates the protection of Geldanamycin on neuronal injury induced by oxygen-glucosedeprivation combined with zVAD in primary cortical neurons. J Neurochem. 2012 Jan;120(1):70-7. [3]. Lin Z, et al. 17-ABAG, a novel Geldanamycin derivative, inhibits LNCaP-cell proliferation through heat shock protein 90 inhibition. Int J Mol Med. 2015 Aug;36(2):424-32. [4]. Roe SM, et al. Structural basis for inhibition of the Hsp90 molecular chaperone by the antitumor antibiotics radicicol and geldanamycin. J Med Chem. 1999 Jan 28;42(2):260-6.

Chemical & Physical Properties

Density	1.2±0.1 g/cm3
Boiling Point	783.9±60.0 °C at 760 mmHg
Melting Point	255 °C
Molecular Formula	C₂₉H₄₀N₂O₉
Molecular Weight	560.636
Flash Point	427.9±32.9 °C
Exact Mass	560.273376
PSA	163.48000
LogP	2.00
Vapour Pressure	0.0±6.2 mmHg at 25°C
Index of Refraction	1.559
InChIKey	QTQAWLPCGQOSGP-ZJNPAGHJSA-N
SMILES	COC1=C2CC(C)CC(OC)C(O)C(C)C=C(C)C(OC(N)=O)C(OC)C=CC=C(C)C(=O)NC(=CC1=O)C2=O
Storage condition	−20°C
Water Solubility	DMSO: soluble

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: LX8920000

CHEMICAL NAME :: Geldanamycin

CAS REGISTRY NUMBER :: 30562-34-6

LAST UPDATED :: 199612

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C29-H40-N2-O9

MOLECULAR WEIGHT :: 560.71

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2500 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >50 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >4200 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: DNA inhibition

TEST SYSTEM :: Rodent - mouse Lymphocyte

DOSE/DURATION :: 1 mg/L

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 35,886,1982

Safety Information

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes	T: Toxic;
Risk Phrases	R36/37/38
Safety Phrases	26-27-36/37/39
RIDADR	NONH for all modes of transport
WGK Germany	2
RTECS	LX8920000
HS Code	2933990090

Customs

HS Code	2933990090
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles12

The induction of heme oxygenase-1 suppresses heat shock protein 90 and the proliferation of human breast cancer cells through its byproduct carbon monoxide.

Toxicol. Appl. Pharmacol. 274(1) , 55-62, (2014)

Heme oxygenase (HO)-1 is an oxidative stress-response enzyme which catalyzes the degradation of heme into bilirubin, ferric ion, and carbon monoxide (CO). Induction of HO-1 was reported to have antitu...

Bioreduction of aryl azides during mutasynthesis of new ansamitocins.

Org. Lett. 15(17) , 4442-5, (2013)

Supplementing a culture of a mutant strain of Actinosynnema pretiosum that is unable to biosynthesize aminohydroxy benzoic acid (AHBA), with 3-azido-5-hydroxy-benzoic acid and 3-azido-5-amino-benzoic ...

Flotillin depletion affects ErbB protein levels in different human breast cancer cells.

Biochim. Biophys. Acta 1843(9) , 1987-96, (2014)

The ErbB3 receptor is an important regulator of cell growth and carcinogenesis. Among breast cancer patients, up to 50-70% have ErbB3 overexpression and 20-30% show overexpressed or amplified ErbB2. E...

Synonyms

2-Azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9-[(aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-, (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-

GELDANAMYCIN,STREPTOMYCES HYGROSCOPICUS

Streptomyces hygroscopicus

GELDANAMYCIN FROM STRE

2-Azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione, 9-[(aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-, (4Z,6Z,8S,9R,10Z,12R,14R,16R)-

(4Z,6Z,8S,9R,10Z,12R,14R,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

Geldanamycin

MFCD00274570

Geldanamycin from Streptomyces hygroscopicus

(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

Geldanamycin (9CI)

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