Hypothemycin
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    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.


Chemical Structure

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Hypothemycin
CAS# 76958-67-3

Theoretical Analysis

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

Size Price Shipping out time Quantity
1mg USD 380 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2021-03-08. Prices are subject to change without notice.

Hyptothemyicin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.

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

Handling Instructions:

Preparing Stock Solutions

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.

Select a batch to recalculate based on the batch molecular weight:
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

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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).



Additional Information