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ascomycin

AlkaPlorer ID: AK016302

Synonym: 'ASCOMYCIN', 'SMR000127507', 'Ascomycin', 'FR 900520', 'FK520', 'MLS000517271', 'FR-900520', 'Immunomycin', 'Changchuanmycin', 'FR 520', 'MLSMR', 'FK 520', 'L 683590', 'ascomycin', 'ascomycin (major)'

IUPAC Name: (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-17-ethyl-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone

Structure

SMILES: CC[C@@H]1/C=C(\C)C[C@H](C)C[C@H](OC)[C@H]2O[C@@](O)(C(=O)C(=O)N3CCCC[C@H]3C(=O)O[C@H](/C(C)=C/[C@@H]3CC[C@@H](O)[C@H](OC)C3)[C@H](C)[C@@H](O)CC1=O)[C@H](C)C[C@@H]2OC

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InChI: InChI=1S/C43H69NO12/c1-10-30-18-24(2)17-25(3)19-36(53-8)39-37(54-9)21-27(5)43(51,56-39)40(48)41(49)44-16-12-11-13-31(44)42(50)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-32(45)35(22-29)52-7/h18,20,25,27-33,35-39,45-46,51H,10-17,19,21-23H2,1-9H3/b24-18+,26-20+/t25-,27+,28+,29-,30+,31-,32+,33-,35+,36-,37-,38+,39+,43+/m0/s1

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InChIKey: ZDQSOHOQTUFQEM-NURRSENYSA-N

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Properties Information

Molecule Weight: 792.0200000000002

TPSA？: 178.35999999999996

MolLogP？: 4.472900000000004

Number of H-Donors: 3

Number of H-Acceptors: 12

RingCount: 4

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Cryptococcus neoformans Cryptococcus neoformans FICI 0.5 None 10.1021/acs.jnatprod.9b00144
Homo sapiens DNA-(apurinic or apyrimidinic site) lyase Potency 15848.9 nM None
Homo sapiens FK506-binding protein 1A EC50 1.6 nM 10.1016/S0960-894X(01)80264-X
Homo sapiens FK506-binding protein 1A EC50 1.6 nM 10.1016/S0960-894X(01)80265-1
Homo sapiens FK506-binding protein 1A EC50 1.6 nM 10.1016/s0960-894x(98)00397-7
Homo sapiens FK506-binding protein 1A EC50 1.6 nM 10.1016/s0960-894x(99)00335-2
Homo sapiens FK506-binding protein 1A IC50 2.1 nM 10.1021/jm960066y
Homo sapiens FK506-binding protein 1A IC50 2.1 nM 10.1021/jm980252z
Homo sapiens FK506-binding protein 1A rIC50 0.9 None 10.1016/s0960-894x(98)00702-1
Homo sapiens FK506-binding protein 1A Selectivity 8.4 None 10.1021/jm960066y
Homo sapiens FK506 binding protein 4 IC50 8000.0 nM 10.1021/jm9903139
Homo sapiens Histone deacetylase 6 Inhibition -0.72 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 23.94 % 10.6019/CHEMBL4808148
Homo sapiens Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 Potency 3981.1 nM None
Homo sapiens Homo sapiens IC50 0.25 nM 10.1016/s0960-894x(98)00145-0
Homo sapiens Homo sapiens IC50 0.25 nM 10.1021/jm960066y
Homo sapiens Homo sapiens IC50 0.26 nM 10.1021/jm980252z
Homo sapiens Homo sapiens IC50 2.06 nM 10.1016/s0960-894x(98)00145-0
Homo sapiens Liver microsome T1/2 0.04 hr 10.1039/C2MD20266B
Homo sapiens Regulator of G-protein signaling 4 Potency 474.4 nM None
Homo sapiens Thyroid hormone receptor beta-1 Potency 39.8 nM None
Mus musculus Murine T-cell line IC50 0.69 nM 10.1016/0960-894X(95)00161-L
Mus musculus Mus musculus IC50 0.69 nM 10.1016/S0960-894X(01)80265-1
Mus musculus Mus musculus IC50 0.69 nM 10.1016/s0960-894x(99)00335-2
Mus musculus Mus musculus rIC50 1.9 None 10.1016/s0960-894x(98)00702-1
Mus musculus Nuclear receptor ROR-gamma Potency 6309.6 nM None
Rattus norvegicus Rattus norvegicus ED50 0.3 mpk/d 10.1021/jm960066y
Rattus norvegicus Rattus norvegicus ED50 0.31 mg.kg-1 10.1016/s0960-894x(98)00145-0
Rattus norvegicus Rattus norvegicus ED50 0.32 mg kg-1 day-1 10.1021/jm980252z
None ADMET T1/2 0.29 hr 10.1039/C2MD20266B
None No relevant target LogD6.5 3.98 None 10.1016/s0960-894x(98)00145-0
None No relevant target LogD7.4 4.22 None 10.1016/s0960-894x(98)00145-0
None No relevant target Solubility 1.6 ug.mL-1 10.1016/s0960-894x(98)00145-0
None No relevant target Solubility 4.2 ug.mL-1 10.1016/s0960-894x(98)00145-0
None No relevant target Solubility 40200.0 nM 10.1039/C2MD20266B
None T-cell IC50 0.69 nM 10.1016/S0960-894X(01)80264-X
None T-cell IC50 0.69 nM 10.1016/S0960-894X(01)81248-8
None T-cell IC50 0.69 nM 10.1016/S0960-894X(97)00409-5
None T-cell IC50 0.69 nM 10.1016/s0960-894x(98)00397-7
None Unchecked IC50 0.205 nM 10.1039/C2MD20266B
None Unchecked Potency 15848.9 nM None
None Unchecked Potency 28183.8 nM None
None Unchecked Potency 35481.3 nM None
None Unchecked rIC50 1.7 None 10.1016/s0960-894x(98)00702-1

Metabolism Information