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microcystin-LR

AlkaPlorer ID: AK002613

Synonym: '(6Z)-Adda5MC-LR'

IUPAC Name: (5R,8S,11R,12S,15S,18S,19S,22R)-15-[3-(diaminomethylideneamino)propyl]-18-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dienyl]-1,5,12,19-tetramethyl-2-methylidene-8-(2-methylpropyl)-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptazacyclopentacosane-11,22-dicarboxylic acid

Structure

SMILES: C=C1C(=O)N[C@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(=O)O)[C@H](C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](/C=C/C(C)=C/[C@H](C)[C@H](CC2=CC=CC=C2)OC)[C@H](C)C(=O)N[C@@H](C(=O)O)CCC(=O)N1C

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InChI: InChI=1S/C49H74N10O12/c1-26(2)23-37-46(66)58-40(48(69)70)30(6)42(62)55-35(17-14-22-52-49(50)51)45(65)54-34(19-18-27(3)24-28(4)38(71-10)25-33-15-12-11-13-16-33)29(5)41(61)56-36(47(67)68)20-21-39(60)59(9)32(8)44(64)53-31(7)43(63)57-37/h11-13,15-16,18-19,24,26,28-31,34-38,40H,8,14,17,20-23,25H2,1-7,9-10H3,(H,53,64)(H,54,65)(H,55,62)(H,56,61)(H,57,63)(H,58,66)(H,67,68)(H,69,70)(H4,50,51,52)/b19-18+,27-24+/t28-,29-,30-,31+,34-,35-,36+,37-,38-,40+/m0/s1

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InChIKey: ZYZCGGRZINLQBL-GWRQVWKTSA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Microcystis aeruginosa Microcystis Microcystaceae Chroococcales Cyanophyceae Cyanobacteriota None Bacteria

Properties Information

Molecule Weight: 995.189

TPSA？: 340.64

MolLogP？: 0.8280700000000023

Number of H-Donors: 11

Number of H-Acceptors: 11

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Gallus gallus Serine-threonine protein phosphatase 2A regulatory subunit IC50 0.1 nM 10.1021/jm010066k
Gallus gallus Serine-threonine protein phosphatase 2A regulatory subunit IC50 3.0 nM 10.1016/s0960-894x(03)00589-4
Homo sapiens A549 EC50 35000.0 nM 10.1021/acs.jnatprod.7b00986
Homo sapiens HCT-116 EC50 35000.0 nM 10.1021/acs.jnatprod.7b00986
Homo sapiens Protein phosphatase 2C alpha IC50 3.0 nM 10.1016/s0960-894x(03)00589-4
Homo sapiens Protein phosphatase 2C alpha Ratio 1.0 None 10.1016/s0960-894x(03)00589-4
Homo sapiens Protein-tyrosine phosphatase 1B IC50 0.1 nM 10.1016/S0960-894X(00)80281-4
Homo sapiens Protein-tyrosine phosphatase 1B IC50 1.17 nM 10.1021/jm960873x
Homo sapiens Serine/threonine protein phosphatase 2A, 55 kDa regulatory subunit B, alpha isoform IC50 0.065 nM 10.1021/jm960873x
Homo sapiens Serine/threonine protein phosphatase 2A, 56 kDa regulatory subunit, alpha isoform IC50 0.1 nM 10.1016/S0960-894X(00)80281-4
Homo sapiens Serine/threonine-protein phosphatase 5 IC50 1.0 nM 10.1021/acs.jmedchem.1c00631
Homo sapiens Serine/threonine protein phosphatase PP1-gamma catalytic subunit IC50 0.01 nM 10.1021/jm010066k
Homo sapiens Serine/threonine protein phosphatase PP1-gamma catalytic subunit IC50 0.02 nM 10.1021/jm010066k
Homo sapiens Serine/threonine protein phosphatase PP1-gamma catalytic subunit IC50 0.56 nM 10.1021/jm010066k
Homo sapiens Serine/threonine protein phosphatase PP1-gamma catalytic subunit IC50 0.8 nM 10.1021/jm010066k
Homo sapiens Serine/threonine protein phosphatase PP1-gamma catalytic subunit IC50 1.9 nM 10.1021/jm010066k
Homo sapiens Serine/threonine protein phosphatase PP1-gamma catalytic subunit IC50 29.0 nM 10.1021/jm010066k
Homo sapiens Serine/threonine protein phosphatase PP1-gamma catalytic subunit IC50 35.0 nM 10.1021/jm010066k
Homo sapiens Serine/threonine protein phosphatase PP1-gamma catalytic subunit IC50 200.0 nM 10.1021/jm010066k
Homo sapiens Solute carrier organic anion transporter family member 1A2 Km 20000.0 nM 10.1016/j.taap.2004.08.012
Homo sapiens Solute carrier organic anion transporter family member 1B1 Km 12400.0 nM 10.1016/j.taap.2004.08.012
Homo sapiens Solute carrier organic anion transporter family member 1B3 Km 12400.0 nM 10.1016/j.taap.2004.08.012
Homo sapiens Solute carrier organic anion transporter family member 2B1 Activity nan None 10.1016/j.taap.2004.08.012
Mus musculus Mus musculus DOSE 1.0 mg.kg-1 10.1016/S0960-894X(00)80281-4
Mus musculus Mus musculus ED50 1.3 nM 10.1016/S0960-894X(00)80281-4
Mus musculus Mus musculus ED50 8.0 nM 10.1016/S0960-894X(00)80281-4
Mus musculus Mus musculus ED50 68.0 nM 10.1016/S0960-894X(00)80281-4
Mus musculus NIH3T3 Activity nan None 10.1021/jm900502e
Rattus norvegicus Hepatocyte Activity nan None 10.1021/jm900502e
Rattus norvegicus Hepatocyte LC50 270.0 nM 10.1021/jm900502e
Rattus norvegicus Solute carrier organic anion transporter family member 1A1 Activity nan None 10.1016/j.taap.2004.08.012
Rattus norvegicus Solute carrier organic anion transporter family member 1A4 Activity nan None 10.1016/j.taap.2004.08.012
Rattus norvegicus Solute carrier organic anion transporter family member 1B2 Activity nan None 10.1016/j.taap.2004.08.012
None Hepatotoxicity Hepatotoxicity nan None 10.1021/tx1000865
None Hepatotoxicity Hepatotoxicity nan None 10.1124/dmd.110.035113
None No relevant target LogD -8.5 None 10.1021/jm900502e
None No relevant target LogD -7.4 None 10.1021/jm900502e
None Unchecked ED50 0.32 nM 10.1016/S0960-894X(00)80388-1
None Unchecked ED50 0.44 nM 10.1016/S0960-894X(00)80388-1
None Unchecked ED50 0.8 nM 10.1016/S0960-894X(00)80388-1
None Unchecked ED50 5.2 nM 10.1016/S0960-894X(00)80388-1
None Unchecked ED50 7.8 nM 10.1016/S0960-894X(00)80388-1
None Unchecked IC50 0.008 nM 10.1021/jm010066k
None Unchecked IC50 0.1 nM 10.1021/acs.jmedchem.1c00631
None Unchecked IC50 0.1 nM 10.1021/jm010066k
None Unchecked IC50 0.15 nM 10.1021/acs.jmedchem.1c00631
None Unchecked IC50 1.0 nM 10.1021/jm010066k
None Unchecked IC50 10.0 nM 10.1021/acs.jmedchem.1c00631
None Unchecked IC50 200.0 nM 10.1021/acs.jmedchem.1c00631
None Unchecked IC50 200000.0 nM 10.1016/0960-894X(96)00378-2
None Unchecked IC50 nan None 10.1021/jm010066k
None Unchecked Inhibition nan % 10.1016/j.bmc.2012.04.046
None Unchecked Inhibition nan % None

Metabolism Information