Compound: methacycline
SMILES: O=C1c2c(O)cccc2C(=C)[C@@H]3C1=C(O)[C@]4(O)C(=O)C(=C(O)[C@H]([C@@H]4[C@H]3O)N(C)C)C(=O)N
InChIKey: MHIGBKBJSQVXNH-IWVLMIASSA-N
Synonyms: methacycline, Metacycline, 914-00-1, Rondomycin, Methylenecycline, Tri-methacycline, Methacyclinum, Metaciclina, Metacyclinum, 6-Methylene-5-hydroxytetracycline, 6-Methylene-5-oxytetracycline, GS-2876, 6-Methyleneoxytetracycline, 6-Deoxy-6-demethyl-6-methylene-5-oxytetracycline, Bialatan, 6-Demethyl-6-deoxy-5-hydroxy-6-methylenetetracycline, Methacycline base, (4S,4aR,5S,5aR,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylidene-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide, Physiomycine, Metacycline (INN), Metacycline [INN], Methacycline amphoteric, MOTC, Methacycline (USAN), CHEBI:6805, IR235I7C5P, 4-(Dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-2-naphthacenecarboxamide, Oxytetracycline, 6-methylene-, METHACYCLINE [USAN], (4S,4aR,5S,5aR,12aR)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methylidene-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide, (4S,4aR,5S,5aR,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-1,4,4a,5,5a,6,11,12a-octahydrotetracene-2-carboxamide, Metacyclinum [INN-Latin], Methacycline [USAN:BAN], Metaciclina [INN-Spanish], CHEBI:6806, GS 2876, HSDB 3118, EINECS 213-017-5, UNII-IR235I7C5P, Spectrum_000381, (4S,4aR,5S,5aR,12aS)-4-(dimethylamino)-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide, Prestwick0_000964, Prestwick1_000964, Prestwick2_000964, Prestwick3_000964, Spectrum2_001398, Spectrum3_000917, Spectrum4_001016, Spectrum5_001576, METHACYCLINE [MI], Doxycycline EP Impurity B, METHACYCLINE [HSDB], SCHEMBL4014, SCHEMBL4015, METHACYCLINE [VANDF], BSPBio_000967, DOXYCYCLINE IMPURITY B, KBioGR_001511, KBioSS_000861, METACYCLINE [WHO-DD], METHACYCLINE [MART.], 2-Naphthacenecarboxamide, 4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, (4S-(4alpha,4aalpha,5alpha,5aalpha,12aalpha))-, 914-00-1(free base), DivK1c_000591, SPBio_001416, SPBio_002888, BPBio1_001065, CHEMBL249837, orb2802244, DTXSID2023272, SCHEMBL19555132, SCHEMBL29376851, SCHEMBL29537520, GTPL13618, KBio1_000591, KBio2_000861, KBio2_003429, KBio2_005997, KBio3_001894, Doxycycline hyclate EP impurity B, NINDS_000591, XIYOPDCBBDCGOE-IWVLMIASSA-N, KUC106428N, 2-NAPHTHACENECARBOXAMIDE, 4-(DIMETHYLAMINO)-1,4,4A,5,5A,6,11,12A-OCTAHYDRO-3,5,10,12,12A-PENTAHYDROXY-6-METHYLENE-1,11-DIOXO-, (4S-(4.ALPHA.,4A.ALPHA.,5.ALPHA.,5A.ALPHA.,12A.ALPHA.))-, KSC-12-231A, BDBM50103629, BDBM50565697, EBC-27111, AKOS015961140, DB00931, IDI1_000591, NCGC00179358-01, NCGC00179358-03, NCGC00179358-05, NCGC00179358-06, NCGC00179358-10, AC-13213, SBI-0051637.P002, AB00514707, CS-0643519, NS00011900, C07654, D04972, G76918, AB00053593-03, AB00053593_04, AB00053593_05, EN300-7481364, DOXYCYCLINE HYCLATE IMPURITY B [EP IMPURITY], Q2365033, DOXYCYCLINE MONOHYDRATE IMPURITY B [EP IMPURITY], 2-Naphthacenecarboxamide,4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,5,10,12,12a-pentahydroxy-6-methylene-1,11-dioxo-, (4S,4aR,5S,5aR,12aS)-
Theoretical properties:
molecular_formula: C22H22N2O8
molecular_weight: 442.4 g/mol
exact_mass: 442.13761566 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 6
hydrogen_bond_acceptor_count: 9
rotatable_bond_count: 2
heavy_atom_count: 32
topological_polar_surface_area: 182 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Methacycline is a tetracycline that is the 6-methylene analogue of oxytetracycline, obtained by formal dehydration at position 6. It has a role as an antibacterial drug. It is a tertiary alpha-hydroxy ketone, a primary carboxamide and a member of tetracyclines.
chebi: A tetracycline that is the 6-methylene analogue of oxytetracycline, obtained by formal dehydration at position 6.
chembl: METHACYCLINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Metacycline or methacycline is a tetracycline antibiotic. It is used as a precursor in the industrial synthesis of doxycycline hyclate.
It has been found to act as an agonist of the human pregnane X receptor ligand-binding domain and to induce CYP3A4 expression in vitro.