Heronamide C
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| Category | Others |
| Catalog number | BBF-04255 |
| CAS | 1257083-94-5 |
| Molecular Weight | 449.62 |
| Molecular Formula | C29H39NO3 |
| Purity | >95% by HPLC |
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Description
It is an unusual polyene macrocyclic lactam containing two isolated tetraene and triene chromophores. It induces a unique reversible vacuolisation of mammalian tumor cells by a yet unidentified mechanism.
Specification
| Synonyms | 9S,10R-dihydroxy-7,15-dimethyl-20R-(2E,4E)-2,4-octadien-1-yl-azacycloeicosa-3E,5E,7E,11Z,13E,15E,17E-heptaen-2-one |
| Storage | Store at -20°C |
| IUPAC Name | (3E,5E,7E,9S,10R,11Z,13E,15E,17E,20R)-9,10-dihydroxy-7,15-dimethyl-20-[(2E,4E)-octa-2,4-dienyl]-1-azacycloicosa-3,5,7,11,13,15,17-heptaen-2-one |
| Canonical SMILES | CCCC=CC=CCC1CC=CC=C(C=CC=CC(C(C=C(C=CC=CC(=O)N1)C)O)O)C |
| InChI | InChI=1S/C29H39NO3/c1-4-5-6-7-8-9-19-26-20-13-10-16-24(2)17-11-14-21-27(31)28(32)23-25(3)18-12-15-22-29(33)30-26/h6-18,21-23,26-28,31-32H,4-5,19-20H2,1-3H3,(H,30,33)/b7-6+,9-8+,13-10+,17-11+,18-12+,21-14-,22-15+,24-16+,25-23+/t26-,27-,28+/m1/s1 |
| InChI Key | QUZNSWBEDCHESP-MRHHRLSKSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White to Pale Yellow Solid |
| Boiling Point | 668.3±55.0°C at 760 mmHg |
| Density | 1.0±0.1 g/cm3 |
| Solubility | Soluble in DMF, DMSO; Moderately soluble in Methanol, Ethanol; Poorly soluble in Water |
Reference Reading
1. Synchronous intramolecular cycloadditions of the polyene macrolactam polyketide heronamide C
Robert J Capon, Barrie Wilkinson, Silke Alt, Thomas J Booth Chem Commun (Camb) . 2016 May 11;52(38):6383-6. doi: 10.1039/c6cc01930g.
A growing number of natural products appear to arise from biosynthetic pathways that involve pericyclic reactions. We show here that for the heronamides this can occur via two spontaneous pathways involving alternative thermal or photochemical intramolecular cycloadditions.
2. Stereochemical Assignment and Biological Evaluation of BE-14106 Unveils the Importance of One Acetate Unit for the Antifungal Activity of Polyene Macrolactams
Hideaki Kakeya, Kohei Fujita, Naoki Ishikawa, Midori A Arai, Shinichi Nishimura, Ryosuke Sugiyama, Masami Ishibashi J Nat Prod . 2016 Jul 22;79(7):1877-80. doi: 10.1021/acs.jnatprod.6b00250.
Heronamides are a class of potent antifungal metabolites produced by marine-derived actinomycetes. The number of hydroxy groups and the stereochemistry of the two hydroxylated methine carbons are important for the activity of heronamide C, whereas the effect of the hydrocarbon chains is not known. In this study, the stereochemistry and the biological activity of BE-14106, another member of the heronamide class of antibiotics, isolated from an actinomycete Actinoalloteichus cyanogriseus IFM 11549 was investigated. Spectroscopic analysis coupled with photo- and O2-induced conversion revealed that BE-14106 and the heronamides had the same stereochemistry. BE-14106 showed potent growth inhibition against fission yeast cells with an MIC value of 0.50 μM (0.21 μg/mL), being 4 times less potent than heronamide C, which revealed the importance of the structure of the hydrocarbon tail for the activity.
3. Toward the Creation of Induced Pluripotent Small (iPS) Molecules: Establishment of a Modular Synthetic Strategy for the Heronamide C-type Polyene Macrolactams and Their Conformational and Reactivity Analysis
Hideaki Kakeya, Yuta Terajima, Ryusei Terashima, Yusuke Sasano, Shinichi Nishimura, Suguru Tanaka, Shota Nagasawa, Hiromichi Nishiyama, Naoki Kanoh, Yoshiharu Iwabuchi J Org Chem . 2021 Dec 3;86(23):16231-16248. doi: 10.1021/acs.joc.1c01760.
A highly modular synthetic strategy for the heronamide C-type polyene macrolactams was established by synthesizing 8-deoxyheronamide C (2). The developed strategy enabled not only the total synthesis of 8-deoxyheronamide C (2) but also the unified synthesis of four heronamide-like molecules named "heronamidoids" (5-8). Conformational and reactivity analysis of the heronamidoids clarified that (1) the C19 stereochemistry mainly affected the conformation of the amide linkage, resulting in the change of alignment of two polyene units and reactivity toward photochemical [6π + 6π] cycloaddition, and (2) the C8,C9-diol moiety is important for the conversion to the heronamide A-type skeleton from the heronamide C skeleton.
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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 ╳
