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Radicicol

Radicicol structure

CAS No:
12772-57-5
Formula:
C18H17ClO6
Chemical Name:
Radicicol
Synonyms:
6H-Oxireno[e][2]benzoxacyclotetradecin-6,12(7H)-dione,8-chloro-1a,14,15,15a-tetrahydro-9,11-dihydroxy-14-methyl-,(1aR,2Z,4E,14R,15aR)-;Radicicol;β-Resorcylic acid,5-chloro-6-(7,8-epoxy-10-hydroxy-2-oxo-3,5-undecadienyl)-,μ-lactone;(1aR,2Z,4E,14R,15aR)-8-Chloro-1a,14,15,15a-tetrahydro-9,11-dihydroxy-14-methyl-6H-oxireno[e][2]benzoxacyclotetradecin-6,12(7H)-dione;Monorden;Monordene;Radisicol;NSC 294404;Radicicol R 2146;Monorden A;(+)-Monorden A;Radicolol;5137-90-6;11021-61-7;957231-40-2
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

SolidChEBI: An antifungal macrolactone antibiotic, obtained from Diheterospora chlamydosporia and Chaetomium chiversii that inhibits protein tyrosine kinase and heat shock protein 90 (Hsp90).

Radicicol Basic Attributes

Molecular Weight：

364.78

Exact Mass：

364.78

DSSTox ID：

DTXSID2042692

HScode：

29322090

Characteristics

PSA：

96.36000

XLogP3：

1.53

Appearance：

yellow solid

Density：

1.364±0.06 g/cm3(Predicted)

Melting Point：

193.5 °C

Boiling Point：

656.2±55.0 °C(Predicted)

Flash Point：

350.7±31.5 °C

Refractive Index：

1.583

Water Solubility：

ethanol: 10 mg/mL

Storage Conditions：

−20°C

Specific rotation：

D20 +203° (chloroform)

Safety Information

Transport codes：

UN 2811 6.1/PG 3

wgk germany：

hazard class code：

22-36/37/38-46-45

safety instructions：

26-45-53

RTECS Number：

RR1105000

Marks：

Xn,T

Precautionary statement(s)：

Missing Phrase - N15.00950417-P201-P280-P308 + P313

Hazard Statements：

H301-H340-H350

GHS Classification：

|Danger|H301 (99.24%): Toxic if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 131 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

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 destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)|Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585) (See all compounds classified as Antimalarials.)

MeSH Entry Terms：

5-chloro-6-(7,8-epoxy-10-hydroxy-2-oxo-3,5-undecadienyl)-beta-resorcylic acid mu-lactone

Radicicol Use and Manufacturing

Radicicol is a resorcylic acid lactone, produced by several fungal species, that exhibits broad spectrum antifungal and antitumor activity. Radicicol has been the subject of extensive investigation and inhibits protein tyrosine kinase, induces the differentiation of HL-60 cells into macrophages, blocks cell cycle at G1 and G2, suppresses NIH 3T3 cell transformation by diverse oncogenes such as src, ras and mos, and also suppresses the expression of mitogen-inducible cyclooxygenase-2. As a cell differentiation modulator, radicicol has anti-angiogenic activity in vivo, inhibiting the proliferation of plasminogen activator production by vascular endothelial cells.

Computed Properties

Molecular Weight:364.8
XLogP3:3.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Exact Mass:364.0713660
Monoisotopic Mass:364.0713660
Topological Polar Surface Area:96.4
Heavy Atom Count:25
Complexity:588
Undefined Atom Stereocenter Count:3
Undefined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Radicicol

CAS No.: 12772-57-5

Content: 97%

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