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Geldanamycin

Geldanamycin structure

CAS No:
30562-34-6
Formula:
C29H40N2O9
Chemical Name:
Geldanamycin
Synonyms:
Geldanamycin;2-Azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione,9,13-dihydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-,9-carbamate;2-Azabicyclo[16.3.1]docosane,geldanamycin deriv.;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-,[8S-(4E,6Z,8R*,9R*,10E,12R*,13S*,14R*,16S*)]-;[8S-(4E,6Z,8R*,9R*,10E,12R*,13S*,14R*,16S*)]-9-[(Aminocarbonyl)oxy]-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-2-azabicyclo[16.3.1]docosa-4,6,10,18,21-pentaene-3,20,22-trione;NSC 122750;NSC 212518;(+)-Geldanamycin;(8S,9S,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;31828-93-0;150575-55-6;1807916-57-9;1955474-12-0
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Geldanamycin is a Hsp90 inhibitor with antimicrobial activity against many Gram-positive and some Gram-negative bacteria.

Geldanamycin Basic Attributes

Molecular Weight：

560.64

Exact Mass：

560.64

DSSTox ID：

DTXSID7042691

HScode：

2933990090

Characteristics

PSA：

164

XLogP3：

3.43750

Appearance：

yellow to orange powder

Density：

1.2±0.1 g/cm3

Melting Point：

252-255 °C

Boiling Point：

783.9°C at 760 mmHg

Flash Point：

87℃

Refractive Index：

1.559

Water Solubility：

DMSO: soluble

Storage Conditions：

−20°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-27-36/37/39-24/25

RTECS Number：

LX8920000

Marks：

T,Xi

Drug Information

MeSH：

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)|Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)|Exogenous and endogenous compounds which inhibit CYSTEINE ENDOPEPTIDASES. (See all compounds classified as Cysteine Proteinase Inhibitors.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

MeSH Entry Terms：

geldanamycin

Geldanamycin Use and Manufacturing

Geldanamycin is benzoquinone ansamycin antibiotic isolated from Streptomyces hygroscopicus. It is a potent antitumor metabolite that acts by binding to the 90-kDa heat-shock protein (Hsp90) essential to maintain the conformation, stability, activity and cellular localisation of several key oncogenic proteins such as ERBB2, C-RAF, CDK4, AKT/PKB, steroid hormone receptors, mutant p53, HIF-1α, survivin and telomerase hTERT.

Computed Properties

Molecular Weight:560.6
XLogP3:2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:5
Exact Mass:560.27338086
Monoisotopic Mass:560.27338086
Topological Polar Surface Area:164
Heavy Atom Count:40
Complexity:1150
Defined Atom Stereocenter Count:6
Defined Bond Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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