| Identification | Back Directory | [Name]
HC TOXIN | [CAS]
83209-65-8 | [Synonyms]
Toxin I
HC TOXIN
HC toxin I
Cyclo(aoe-Pro-Ala-ala)
HC TOXIN FROM HELMINTHOSPORIUM CARBONUM
Cyclo[D-Pro-L-Ala-D-Ala-2-(6-oxo-6-oxiranylhexyl)-L-Gly-]
CYCLO-(D-PRO-L-ALA-D-ALA-L-2-AMINO-8-OXO-9,10-EPOXYDECANOIC ACID)
Cyclo[L-Ala-D-Ala-[(2S)-2-amino*-8-oxo-8-oxiranyloctanoyl]-D-Pro-]
Cyclo(2-amino-8-oxo-9,10-epoxydecanoic acid-prolyl-alanyl-alanine)
Cyclic(L-alanyl-D-alanyl-eta-oxo-L-alpha-aminooxiraneoctanoyl-D-prolyl)
Cyclo(L-alanyl-D-alanyl-8-oxiranyl-8-oxo-L-2-aminooctanoyl-D-prolyl), (S)-
Cyclo(L-alanyl-D-alanyl-(alphas,2S)-alpha-amino-eta-oxooxiraneoctanoyl-D-prolyl)
(3S,6R,9S,12R)-6,9-dimethyl-3-[6-[(2S)-oxiran-2-yl]-6-oxohexyl]-1,4,7,10-tetrazabicyclo[10.3.0]pentadecane-2,5,8,11-tetrone | [Molecular Formula]
C21H32N4O6 | [MDL Number]
MFCD29924706 | [MOL File]
83209-65-8.mol | [Molecular Weight]
436.51 |
| Chemical Properties | Back Directory | [Boiling point ]
819.2±65.0 °C(Predicted) | [density ]
1.28±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: 10 mg/ml; Methanol: 10 mg/ml | [form ]
lyophilized powder | [pka]
13.33±0.70(Predicted) | [color ]
Off-white to light yellow | [InChI]
1S/C21H32N4O6/c1-12-18(27)22-13(2)19(28)24-14(7-4-3-5-9-16(26)17-11-31-17)21(30)25-10-6-8-15(25)20(29)23-12/h12-15,17H,3-11H2,1-2H3,(H,22,27)(H,23,29)(H,24,28) | [InChIKey]
GNYCTMYOHGBSBI-UHFFFAOYSA-N | [SMILES]
CC1NC(=O)C(C)NC(=O)C2CCCN2C(=O)C(CCCCCC(=O)C3CO3)NC1=O |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
25 | [Safety Statements ]
45 | [RIDADR ]
UN 2811 6.1 / PGIII | [WGK Germany ]
3 | [Storage Class]
6.1B - Non-combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | [Hazard Classifications]
Acute Tox. 2 Oral |
| Hazard Information | Back Directory | [Description]
HC Toxin is a cell-permeable, reversible inhibitor of histone deacetylases (HDACs) (IC50 = 30 nM). Through its effects on HDACs, HC toxin has been shown to up-regulate the expression of 15-lipoxygenase-1 in colorectal cancer cells and induce fetal hemoglobin in human primary erythroid cells. HC Toxin is a cyclic tetrapeptide first isolated from H. carbonum (now C. carbonum), a pathogen of maize. | [Uses]
HC Toxin is an HDAC inhibitor. Cyclic tetrapeptide[1] fungal toxin selectively toxic to plants with susceptible host genotype (2) | [Definition]
ChEBI: A homodetic cyclic tetrapeptide made up from L-alanyl, D-alanyl, L-prolyl and 2-amino-8-oxo-9,10-epoxydecanoyl residues. | [Biochem/physiol Actions]
Cyclic tetrapeptide fungal toxin selectively toxic to plants with susceptible host genotype. | [storage]
Store at -20°C | [References]
[1] G BROSCH. Inhibition of maize histone deacetylases by HC toxin, the host-selective toxin of Cochliobolus carbonum.[J]. Plant Cell, 1995, 7 11: 1941-1950. DOI: 10.1105/tpc.7.11.1941
[2] S J DARKIN-RATTRAY. Apicidin: a novel antiprotozoal agent that inhibits parasite histone deacetylase.[J]. Proceedings of the National Academy of Sciences of the United States of America, 1996, 93 23: 13143-13147. DOI: 10.1073/pnas.93.23.13143
[3] H. KAMITANI. Expression of 15-lipoxygenase-1 is regulated by histone acetylation in human colorectal carcinoma.[J]. Carcinogenesis, 2001, 22 1 1: 187-191. DOI: 10.1093/carcin/22.1.187
[4] HUA CAO George S. Histone deacetylase inhibitor FK228 is a potent inducer of human fetal hemoglobin[J]. American Journal of Hematology, 2006, 81 12: 981-983. DOI: 10.1002/ajh.20676
[5] WALTON J. HC-toxin.[J]. Phytochemistry, 2020, 67 14 1: 1406-1413. DOI: 10.32388/5s7act |
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