Details of the Drug

General Information of Drug (ID: DMTMLRN)

Drug Name
MICROCYSTIN-LR
Synonyms
Akerstox; Microcystin-a; 5-L-Argininecyanoginosin LA; Toxin I (Microcystis aeruginosa); Cyanoginosin LA, 5-L-arginine-; Toxin T 17 (Microcystis aeruginosa); BRN 4779759; Toxin, blue green alga, Microcystis aeruginosa; AC1O5MXK; DTXSID00424146; 128657-50-1; LS-55782
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 4 Molecular Weight (mw) 995.2
Logarithm of the Partition Coefficient (xlogp) 2.3
Rotatable Bond Count (rotbonds) 15
Hydrogen Bond Donor Count (hbonddonor) 10
Hydrogen Bond Acceptor Count (hbondacc) 13
Chemical Identifiers
Formula
C49H74N10O12
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
Canonical SMILES
C[C@H]1[C@@H](NC(=O)[C@@H](NC(=O)[C@H]([C@@H](NC(=O)[C@@H](NC(=O)[C@H](NC(=O)C(=C)N(C(=O)CC[C@@H](NC1=O)C(=O)O)C)C)CC(C)C)C(=O)O)C)CCCN=C(N)N)/C=C/C(=C/[C@H](C)[C@H](CC2=CC=CC=C2)OC)/C
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
InChIKey
ZYZCGGRZINLQBL-GWRQVWKTSA-N
Cross-matching ID
PubChem CID
445434
ChEBI ID
CHEBI:6925
CAS Number
101043-37-2
TTD ID
D0O1BJ
VARIDT ID
DR01417

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Serine/threonine PP1-alpha (PPP1CA) TTFLH0E PP1A_HUMAN Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
3-phosphoinositide-dependent protein kinase 1 (PDPK1) OTT09ZVP PDPK1_HUMAN Post-Translational Modifications [3]
Adipogenesis regulatory factor (ADIRF) OTTJP8D4 ADIRF_HUMAN Gene/Protein Processing [4]
Apoptosis regulator BAX (BAX) OTAW0V4V BAX_HUMAN Gene/Protein Processing [5]
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [6]
Arginine/serine-rich protein PNISR (PNISR) OTUM02FW PNISR_HUMAN Gene/Protein Processing [7]
Aromatase (CYP19A1) OTZ6XF74 CP19A_HUMAN Gene/Protein Processing [8]
ATP-binding cassette sub-family C member 2 (ABCC2) OTJSIGV5 MRP2_HUMAN Regulation of Drug Effects [9]
Baculoviral IAP repeat-containing protein 3 (BIRC3) OT3E95KB BIRC3_HUMAN Gene/Protein Processing [5]
Bcl2-associated agonist of cell death (BAD) OT63ERYM BAD_HUMAN Post-Translational Modifications [10]
Beta-galactosidase (GLB1) OTB0TKAG BGAL_HUMAN Gene/Protein Processing [11]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4735).
2 Serine-threonine protein phosphatase inhibitors: development of potential therapeutic strategies. J Med Chem. 2002 Mar 14;45(6):1151-75.
3 p53 Plays an important role in cell fate determination after exposure to microcystin-LR. Environ Health Perspect. 2010 Sep;118(9):1292-8. doi: 10.1289/ehp.1001899. Epub 2010 Apr 26.
4 Gene expression network regulated by DNA methylation and microRNA during microcystin-leucine arginine induced malignant transformation in human hepatocyte L02 cells. Toxicol Lett. 2018 Jun 1;289:42-53. doi: 10.1016/j.toxlet.2018.03.003. Epub 2018 Mar 5.
5 Toxic effects of microcystin-LR on the HepG2 cell line under hypoxic and normoxic conditions. J Appl Toxicol. 2013 Oct;33(10):1180-6. doi: 10.1002/jat.2749. Epub 2012 Apr 27.
6 Alteration of proteins expression in apoptotic FL cells induced by MCLR. Environ Toxicol. 2008 Aug;23(4):451-8. doi: 10.1002/tox.20355.
7 Cytotoxic Effects of Environmental Toxins on Human Glial Cells. Neurotox Res. 2017 Feb;31(2):245-258. doi: 10.1007/s12640-016-9678-5. Epub 2016 Oct 29.
8 Effects of Cyanobacterial Harmful Algal Bloom Toxin Microcystin-LR on Gonadotropin-Dependent Ovarian Follicle Maturation and Ovulation in Mice. Environ Health Perspect. 2023 Jun;131(6):67010. doi: 10.1289/EHP12034. Epub 2023 Jun 21.
9 Human MRP2 exports MC-LR but not the glutathione conjugate. Chem Biol Interact. 2019 Sep 25;311:108761. doi: 10.1016/j.cbi.2019.108761. Epub 2019 Jul 23.
10 Microcystin-LR promotes proliferation by activating Akt/S6K1 pathway and disordering apoptosis and cell cycle associated proteins phosphorylation in HL7702 cells. Toxicol Lett. 2016 Jan 5;240(1):214-25. doi: 10.1016/j.toxlet.2015.10.015. Epub 2015 Oct 23.
11 MC-LR-induced interaction between M2 macrophage and biliary epithelial cell promotes biliary epithelial cell proliferation and migration through regulating STAT3. Cell Biol Toxicol. 2021 Dec;37(6):935-949. doi: 10.1007/s10565-020-09575-9. Epub 2021 Jan 21.