Terreulactone A
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03105 |
| CAS | |
| Molecular Weight | 510.53 |
| Molecular Formula | C28H30O9 |
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Description
Tetracycline A is an acetylcholinesterase (AchE, EC3. 1.1.7) inhibitor produced by Aspergillus terreus. It has a strong inhibition of AchE activity with IC50 of 0.23 µmol/L.
Specification
| Synonyms | 13-hydroxy-16-methoxy-8-(4-methoxyphenyl)-4,14,19,19-tetramethyl-5,9,18-trioxapentacyclo[14.2.1.01,14.04,13.06,11]nonadeca-6(11),7-diene-10,15,17-trione |
| IUPAC Name | (1R,4R,13R,14R,16R)-13-hydroxy-16-methoxy-8-(4-methoxyphenyl)-4,14,19,19-tetramethyl-5,9,18-trioxapentacyclo[14.2.1.01,14.04,13.06,11]nonadeca-6(11),7-diene-10,15,17-trione |
| Canonical SMILES | CC1(C23CCC4(C(C2(C(=O)C1(C(=O)O3)OC)C)(CC5=C(O4)C=C(OC5=O)C6=CC=C(C=C6)OC)O)C)C |
| InChI | InChI=1S/C28H30O9/c1-23(2)27-12-11-24(3)26(32,25(27,4)21(30)28(23,34-6)22(31)37-27)14-17-19(36-24)13-18(35-20(17)29)15-7-9-16(33-5)10-8-15/h7-10,13,32H,11-12,14H2,1-6H3/t24-,25-,26+,27-,28-/m1/s1 |
| InChI Key | AOFMVUCAUSHJLI-RKFAPSRVSA-N |
Properties
| Appearance | White Powder |
| Boiling Point | 701.9±60.0°C at 760 mmHg |
| Density | 1.4±0.1 g/cm3 |
Reference Reading
1. Studies directed toward the synthesis of terreulactone A: rapid construction of the A, B, C rings
Haibo Liu, Dionicio R Siegel, Samuel J Danishefsky Org Lett. 2006 Feb 2;8(3):423-5. doi: 10.1021/ol052618p.
[structure: see text]. An efficient, rapid synthesis of the A, B, C rings of terreulactone A is described. Key steps in the synthesis include a diastereoselective benzylic acid rearrangement to create the desired quaternary center at C2 and a mild bromolactonization to assemble the lactonic ring A.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
