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R0654

Sigma-Aldrich

Reveromycin A

solid

Empirical Formula (Hill Notation):
C36H52O11
CAS Number:
Molecular Weight:
660.79
MDL number:
PubChem Substance ID:

biological source

Streptomyces sp.

Quality Level

form

solid

mol wt

660.79 g/mol

packaging

pkg of 100 μg

color

tan

solubility

DMF: soluble
DMSO: soluble
ethanol: soluble
ethyl acetate: soluble
methanol: soluble
soluble

antibiotic activity spectrum

fungi

Mode of action

protein synthesis | interferes

shipped in

wet ice

storage temp.

−20°C

SMILES string

[H][C@]1(C\C=C(C)\C=C\[C@H](O)[C@@H](C)\C=C\C(O)=O)O[C@]2(CC[C@@H]1C)CC[C@@](CCCC)(OC(=O)CCC(O)=O)[C@@]([H])(O2)\C=C\C(C)=C\C(O)=O

InChI

1S/C36H52O11/c1-6-7-19-35(47-34(44)17-16-32(40)41)21-22-36(46-30(35)14-10-25(3)23-33(42)43)20-18-27(5)29(45-36)13-9-24(2)8-12-28(37)26(4)11-15-31(38)39/h8-12,14-15,23,26-30,37H,6-7,13,16-22H2,1-5H3,(H,38,39)(H,40,41)(H,42,43)/b12-8+,14-10+,15-11+,24-9+,25-23+/t26-,27-,28-,29+,30-,35+,36-/m0/s1

InChI key

ZESGNAJSBDILTB-OXVOKJAASA-N

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This Item
H9773A2411A6191
Reveromycin A solid

Sigma-Aldrich

R0654

Reveromycin A

form

solid

form

lyophilized powder

form

solid

form

lyophilized powder

color

tan

color

faintly brown to brown, white to beige

color

yellow to yellow-orange

color

-

solubility

DMF: soluble, DMSO: soluble, ethanol: soluble, ethyl acetate: soluble, methanol: soluble

solubility

H2O: soluble 50 mg/mL, ethanol: soluble, methanol: soluble

solubility

H2O: slightly soluble

solubility

H2O: 50 mg/mL, 1-butanol: soluble, 1-propanol: soluble, DMSO: soluble, ethanol: soluble, methanol: soluble

antibiotic activity spectrum

fungi

antibiotic activity spectrum

fungi

antibiotic activity spectrum

fungi, yeast

antibiotic activity spectrum

-

mode of action

protein synthesis | interferes

mode of action

protein synthesis | interferes

mode of action

cell membrane | interferes

mode of action

enzyme | inhibits

Biochem/physiol Actions

It is an epidermal growth factor (EGF) and eukaryotic cell growth inhibitor.
Reveromycin A is a polyketide antibiotic from Streptomyces sp. Epidermal growth factor (EGF) inhibitor; apoptosis inducer; G1 phase cell cycle inhibitor having antiproliferative behavior against human cell lines KB and K562 as well as antifungal activity.

Analysis Note

Avoid acidic conditions.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Hiroyuki Osada
Current medicinal chemistry, 10(9), 727-732 (2003-04-08)
In this review, I have mainly described the cell cycle inhibitors isolated from microbial metabolites. Once the molecular target of the inhibitor is determined, the inhibitor can be used as bioprobe to dissect the diverse aspect of biological functions in
Naoyuki Takahashi et al.
Odontology, 95(1), 1-9 (2007-07-31)
Osteoclast function consists of several processes: recognition of mineralized tissues, development of ruffled borders and sealing zones, secretion of acids and proteolytic enzymes into the space beneath the ruffled border, and incorporation and secretion of bone degradation products using the
Saburo Sone et al.
Cancer metastasis reviews, 26(3-4), 685-689 (2007-09-06)
Bone metastasis is a critical problem of lung cancer patients. Reproducible animal models of lung cancer bone metastasis, like NK-cell depleted SCID mouse model with SCB-5 cells, are useful to explore the molecular mechanism and search of molecular targets. SBC-5
Takeshi Shimizu et al.
Bioorganic & medicinal chemistry letters, 18(13), 3756-3760 (2008-06-04)
Various derivatives of reveromycin A, an inhibitor of eukaryotic cell growth, and spirofungin A, focusing on the 5S hydroxyl group and C18 hemisuccinyl group, were synthesized and their inhibitory effects on both the isoleucyl-tRNA synthetase activity and the survival of
T Shimizu et al.
Organic letters, 2(14), 2153-2156 (2000-07-13)
The stereoselective total synthesis of reveromycin A (1), a potent inhibitor of eukaryotic cell growth, has been accomplished on the basis of the stereocontrolled construction of the 6,6-spiroketal system, efficient succinylation of the tert-alcohol under high pressure, and the introduction

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