Compound: cycloleucine
SMILES: O=C(O)C1(N)CCCC1
InChIKey: NILQLFBWTXNUOE-UHFFFAOYSA-N
Synonyms: cycloleucine, 52-52-8, 1-Aminocyclopentanecarboxylic acid, 1-Aminocyclopentane-1-carboxylic acid, Cycloleucin, 1-Amino-1-cyclopentanecarboxylic acid, CYCLO-LEUCINE, 1-Amino-1-carboxycyclopentane, 1-Amino-cyclopentanecarboxylic acid, Cyclopentanecarboxylic acid, 1-amino-, NSC 1026, CB 1639, 1-Aminocyclopentanecarboxylate, X 201, NSC1026, WR 14,997, NSC-1026, aminocyclopentanecarboxylic acid, 0TQU7668EI, Acid, aminocyclopentanecarboxylic, DTXSID5024475, CHEBI:40547, 1 Aminocyclopentanecarboxylic acid, Acid, 1-aminocyclopentanecarboxylic, CB-1639, 1-aminocyclopentane, RefChem:129754, DTXCID304475, 200-144-6, MFCD00001381, CHEMBL295830, 1-amino-1-cyclopentane carboxylic acid, WR 14997, Cycloleucine1-Amino-cyclopentanecarboxylic acid, 1-amino cyclopentane carboxylic acid, 1-aminocyclopentane-1-carboxylate, 1-azaniumylcyclopentane-1-carboxylate, HSDB 5195, EINECS 200-144-6, BRN 0636626, UNII-0TQU7668EI, AI3-26442, Cyclopentanecarboxylic acid, 1-amino-, L-, Leucine, Cyclo-, Amino-1-cyclopentanecarboxylic acid, Cycloleucine, 97%, (2E)-Decenoyl-ACP, Irbesartan Impurity N5, Spectrum_001268, 1y1m, Irbesartan Impurity 37, AC1OCG3T, Spectrum2_000931, Spectrum3_001514, Spectrum4_000340, Spectrum5_001136, CYCLOLEUCINE [MI], Biomol-NT_000201, CYCLOLEUCINE [HSDB], NCIMech_000677, WLN: L5TJ AZ AVQ, SCHEMBL8495, BSPBio_003187, CYCLOLEUCIN [WHO-DD], KBioGR_000719, KBioSS_001748, 4-14-00-00974 (Beilstein Handbook Reference), DivK1c_000723, SPECTRUM1502128, SPBio_000862, 1-amino-Cyclopentanecarboxylate, BPBio1_001084, orb1297971, Cyclopentanecarboxylic acid, L-, 1-Aminocyclopentanecarboxylicacid, HMS502E05, KBio1_000723, KBio2_001748, KBio2_004316, KBio2_006884, KBio3_002687, NILQLFBWTXNUOE-UHFFFAOYSA-, 1-amino-1-Cyclopentanecarboxylate, NINDS_000723, HMS1921L08, 1-ammonio-1-cyclopentanecarboxylate, ALBB-035361, CS-B0093, 1-amino-cyclopentane carboxylic acid, BBL020454, BDBM50070638, CCG-35835, EBC-47318, FD1031, SBB004230, STK133034, ZINC00001234, AKOS000183252, AC-2700, DB04620, IDI1_000723, NCGC00094966-01, NCGC00094966-02, NCGC00094966-03, NCGC00094966-04, NCGC00163268-01, NCGC00178218-01, AC5, AS-11677, HY-30008, NCI60_000070, SY002601, Cycloleucine1-amino-cyclopentanecarboxylate, CYCLOPENTANECARBOXYLIC ACID, L-AMINO, DB-031284, A1063, NS00032521, ST45026863, EN300-39470, 1-Aminocyclopentanecarboxylic acid;Cyclolencine, C03969, A829129, F044737, Q607775, F8881-4536, Z234896477, 3DD7E30B-2149-43D9-A44B-7A59D546A28B, InChI=1/C6H11NO2/c7-6(5(8)9)3-1-2-4-6/h1-4,7H2,(H,8,9)
Theoretical properties:
molecular_formula: C6H11NO2
molecular_weight: 129.16 g/mol
exact_mass: 129.078978594 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 1
heavy_atom_count: 9
topological_polar_surface_area: 63.3 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: CRYSTALS FROM ETHANOL & WATER
color: CRYSTALS FROM ETHANOL & WATER
Descriptions:
{"pubchem": "1-aminocyclopentanecarboxylic acid is a non-proteinogenic alpha-amino acid that is cyclopentane substituted at position 1 by amino and carboxy groups. It has a role as an EC 2.5.1.6 (methionine adenosyltransferase) inhibitor.", "chebi": "A non-proteinogenic \u03b1-amino acid that is cyclopentane substituted at position 1 by amino and carboxy groups.", "chembl": "CYCLOLEUCINE is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Cycloleucine is a non-proteinogenic amino acid. It could be classified as a cyclopentane derivative of norleucine, having two hydrogen atoms less. The \u03b1-carbon atom is not a stereocenter. Cycloleucine is a non-metabolisable amino acid that specifically and reversibly inhibits nucleic acid methylation. It is widely used in biochemical experiments.\nIn 2007, a research study had shown that cycloleucine can lower S-adenosyl methionine (SAM) levels in primary rat hepatocytes by inhibiting the conversion of 5\u2032-methylthioadenosine to SAM through the methionine salvage pathway. Cycloleucine treatment in conjunction with higher levels of cytochrome P450 2E1 (CYP2E1) and lower SAM levels in pyrazole hepatocytes had shown an increased amount of cell apoptosis when compared to control hepatocytes.\nIn a 2015 study on the role of N6-methyladenosine (m6A) demethylation on adipogenesis, researchers treated porcine adipocytes with increasing concentrations of cycloleucine. The researchers measured mRNA concentration of m6A using the dot blot method, and the results showed that cycloleucine increased adipocyte growth by blocking methylation by inhibiting m6A levels relative to the control adipocytes.\nA 2022 study showed that cycloleucine inhibits porcine oocyte and embryo development. Researchers cultured porcine oocytes and isolated cumulus cells from their cumulus cell complexes, after which the cells were cultured in vitro with cycloleucine in increasing concentrations. The samples were monitored under fluorescence microscopy, with the results showing positive relationship between cycloleucine concentration and decreased viability and survival rate for oocytes."}