WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 201495
CAS#: 76958-67-3
Description: Hypothemycin is a resorcylic acid lactone polyketide that has fungicidal, kinase inhibitory, and anticancer properties. Hypothemycin inhibits MEK and other protein kinases containing a conserved cysteine residue in the ATP-binding domain. Hypothemycin inhibits proliferation of cancer cell lines dependent on activating mutations.
MedKoo Cat#: 201495
Name: Hypothemycin
CAS#: 76958-67-3
Chemical Formula: C19H22O8
Exact Mass: 378.13147
Molecular Weight: 378.37
Elemental Analysis: C, 60.31; H, 5.86; O, 33.83
Synonym: Hypothemycin, NSC 354462
IUPAC/Chemical Name: (1aR,3S,4S,9S,15bR,Z)-3,4,12-trihydroxy-14-methoxy-9-methyl-3,4,8,9-tetrahydro-1aH-benzo[c]oxireno[2,3-e][1]oxacyclotetradecine-5,11(2H,15bH)-dione
InChi Key: SSNQAUBBJYCSMY-KNTMUCJRSA-N
InChi Code: InChI=1S/C19H22O8/c1-9-4-3-5-12(20)17(23)14(22)8-15-18(27-15)11-6-10(25-2)7-13(21)16(11)19(24)26-9/h3,5-7,9,14-15,17-18,21-23H,4,8H2,1-2H3/b5-3-/t9-,14-,15+,17+,18+/m0/s1
SMILES Code: O=C1[C@@H](O)[C@@H](O)C[C@]2([H])[C@@](O2)([H])C3=CC(OC)=CC(O)=C3C(O[C@@H](C)C/C=C\1)=O
Appearance: Solid powder
Purity: >98%
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >5 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 378.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1. Agatsuma, T., Takahashi, A., Kabuto, C., et al. Revised structure and stereochemistry of hypothemycin. Chem. Pharm. Bull. 41(2), 373-375 (1993).
2. Xu, L., Xue, J., Wu, P., et al. Antifungal activity of hypothemycin against Peronophythora litchii in vitro and in vivo. J. Agric. Food Chem. 61(42), 10091-10095 (2013).
3. Zhao, A., Lee, S.H., Mojena, M., et al. Resorcylic acid lactones: Naturally occurring potent and selective inhibitors of MEK. J. Antibiot. (Tokyo) 52(12), 1086-1094 (1999).
4. Schirmer, A., Kennedy, J., Murli, S., et al. Targeted covalent inactivation of protein kinases by resorcylic acid lactone polyketides. Proc. Nat. Acad. Sci. USA 103(11), 4234-4239 (2006).
5. Fakhouri, L., El-Elimat, T., Hurst, D.P., et al. Isolation, semisynthesis, covalent docking and transforming growth factor beta-activated kinase 1 (TAK1)-inhibitory activities of (5Z)-7-oxozeaenol analogues. Bioorg. Med. Chem. 23(21), 6993-6999 (2015).
6. Tanaka, H., Nishida, K., Sugita, K., et al. Antitumor efficacy of hypothemycin, a new Ras-signaling inhibitor. Jpn. J. Cancer Res. 90(10), 1139-1145 (1999).
