CC-1014
Basic information
- CAS
76600-38-9- Standard SMILES
CCC(=O)CC(O)CC(C)CC(NC(=O)C1CC(C)CN1C(=O)/C=C/C(C)CC)C(=O)NC(C(=O)NC(C)(C)C(=O)NC(CC(C)C)C(=O)NC(CC(C)C)C(=O)NC(C)(C)C(=O)NC(C)(C)C(=O)NCCC(=O)NC(C)CN(C)C)C(O)C(C)C- InChIKey
FOAIGCPESMNWQP-WCWDXBQESA-N- Molecular formula
- C62H111N11O13
- Average molar mass
- 1,218.6 g/mol
- Monoisotopic mass
- 1,217.83628264
Overview
CC-1014 is a peptide.
Names & identifiers
- Preferred name
- CC-1014
- IUPAC
- N-[1-[[1-[[1-[[1-[[1-[[1-[[1-[[3-[1-(dimethylamino)propan-2-ylamino]-3-oxopropyl]amino]-2-methyl-1-oxopropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-3-hydroxy-4-methyl-1-oxopentan-2-yl]amino]-6-hydroxy-4-methyl-1,8-dioxodecan-2-yl]-4-methyl-1-[(E)-4-methylhex-2-enoyl]pyrrolidine-2-carboxamide
- English name
- Leucinostatin A
- Molecular formula
- C62H111N11O13
- Molecular weight
- 1218.61
Names & synonyms
Antibiotic CC 1014CC-1014CC 1014RefChem:91815481859-20-3Antibiotic 1907-VIIIAntibiotic P-168NSC356885Antibiotic P 168NSC 356885P-168CHEMBL1989620
Show more names
LeucinostatinA20668Leucinostatin ALeucinostatin A DISCONTINUEDTryanocidin, CC 1014, M 13959, ML 1014, P 168, SF 1907VIII, U 53496
SCHEMBL29441505CHEBI:225047NSC-356885.beta.-Alaninamide,6S)-6-hydroxy-4-methyl-8-oxo- L-2-aminodecanoyl-threo-3-hydroxy-L-leucyl- 2-methylalanyl-L-leucyl-L-leucyl-2-methylalanyl- 2-methylalanyl-N-[2-(dimethylamino)-1-methylethyl]-, [1[S-(E)],9(S)]-beta-Alaninamide, cis-4-methyl-1-(4-methyl-1-oxo-2-hexenyl)-L-prolyl-(4S,6S)-6-hydroxy-4-methyl-8-oxo-L-2-aminodecanoyl-threo-3-hydroxy-L-leucyl-2-methylalanyl-L-leucyl-L-leucyl-2-methylalanyl-2-methylalanyl-N-(2-(dimethylamino)-1-methylethyl)-, (1(S-(E)),9(S))-
Database identifiers
- CAS
76600-38-9
Properties
Computed structural properties
- XLogP
- 4.3
- Topological polar surface area
- 343 Ų
- Hydrogen bond donors
- 11
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 37
- Heavy atoms
- 86
- Formal charge
- 0
- Complexity
- 2,340
Physicochemical properties
- Melting point
- 96 · 96-98 °C
- Boiling point
- 1408 · 1408.0±65.0 °C(Predicted)
- Density
- 1.116 · 1.116±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble
- form
- A solid
- pka
- 12.66 · 12.66±0.46(Predicted)
Chemistry & industry
Applications
DescriptionLeucinostatin A is a fungal metabolite originally isolated from P. lilacinus with diverse biological activities. It is active against P. oryzae, B. cinera, P. chrysogenum, X. oryzae, S. cerevisiae, and C. albicans fungi and B. subtilis, S. aureus, S. lutea, and M. phlei bacteria in a disc assay. Leucinostatin A (0.1-1 μg/ml) reduces T cell activation induced by phorbol 12-myristate 13-acetate (TPA; ) or an anti-CD3 antibody in a concentration-dependent manner. It inhibits proliferation of DU145 prostate cancer cells co-cultured with PrSC stromal cells in vitro (IC50 = 0.045 μg/ml).
UsesLeucinostatin A is a broadly bioactive component produced byPaecilomyces lilacinus..
UsesLeucinostatin A is the major component of an atypical nonapeptide complex produced by Paecilomyces lilacinus, first reported in 1973. Leucinostatins display broad bioactivity against Gram positive bacteria, fungi, plants and tumour cell lines. Leucinostatin A inhibits respiration by uncoupling oxidative phosphorylation and is potentiated by inhibitors such as venturicidin and oligomycin. More recently, interest in leucinostatin has focused on understanding its activity as an insulin-like growth factor I regulator, an ionophore, inhibitor of cell surface expression of viral glycoproteins and its anti-trypanosomal activity.
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