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Herbimycin A

Herbimycin A structure

CAS No:
70563-58-5
Formula:
C30H42N2O9
Chemical Name:
Herbimycin A
Synonyms:
Geldanamycin,17-demethoxy-15-methoxy-11-O-methyl-,(15R)-;2-Azabicyclo[16.3.1]docosane,geldanamycin deriv.;(15R)-17-Demethoxy-15-methoxy-11-O-methylgeldanamycin;Herbimycin A;Antibiotic TAN 420F;NSC 305978;1258005-88-7
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

ChEBI: A 19-membered macrocyle incorporating a benzoquinone ring and a lactam functionality. It is an ansamycin antibiotic that induces apoptosis and displays antitumour effects.

Herbimycin A Basic Attributes

Molecular Weight：

574.66

Exact Mass：

574.66

DSSTox ID：

DTXSID4042674

HScode：

29419000

Characteristics

PSA：

152.48000

XLogP3：

2.12

Appearance：

yellow powder

Density：

1.2±0.1 g/cm3

Melting Point：

229-231 °C

Boiling Point：

752℃

Flash Point：

>110°(230°F)

Refractive Index：

1.545

Water Solubility：

DMSO: 7.5 mg/mL DMSO stock solution can be diluted in phosphate buffered saline. The ratio of buffer:DMSO should be greater than 500:1.

Storage Conditions：

−20°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

22-24/25-36-26

RTECS Number：

LX8930000

Marks：

Drug Information

MeSH：

Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms. (See all compounds classified as Antibiotics, Antineoplastic.)|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.)|Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

MeSH Entry Terms：

geldanamycin, 17-demethoxy-15-methoxy-11-O-methyl-, (15R)-

Herbimycin A Use and Manufacturing

Herbimycin A is a benzoquinone ansamycin antibiotic from Streptomyces. It has herbicidal activity and acts as a cell-permeable inhibitor of non-receptor tyrosine kinases and the heat shock protein Hsp90. Herbimycin A inhibits Bcr-Abl with an IC50 value of 5 μM, a concentration that also effectively blocks Src, Yes, Fps, Ros, and ErbB but not protein kinases (PK) PKA, PKC, Rac, Myc, or Raf. Presumably through its effects on tyrosine kinase signaling, herbimycin A also impairs endothelial cell proliferation in the context of angiogenesis, NF-κB activation, phosphorylation of phospholipase C-γ1, and eggshell formation in schistosome parasites. Ansamycins, including herbimycin A and geldanamycin , bind Hsp90 and destabilize client proteins, including Src, Bcr-Abl, and ErbB2, leading to their ubiquitination and proteasomal degradation.

Computed Properties

Molecular Weight:574.7
XLogP3:1.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:6
Exact Mass:574.28903092
Monoisotopic Mass:574.28903092
Topological Polar Surface Area:153
Heavy Atom Count:41
Complexity:1150
Undefined Atom Stereocenter Count:7
Undefined Bond Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Herbimycin A

CAS No.: 70563-58-5

Content: 0.98%

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