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
CHEMBL444092
CAS Number
101043-37-2
TTD ID
D0O1BJ
VARIDT ID
DR01417
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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
Adipogenesis regulatory factor (ADIRF) OTTJP8D4 ADIRF_HUMAN Gene/Protein Processing [3]
Arginine/serine-rich protein PNISR (PNISR) OTUM02FW PNISR_HUMAN Gene/Protein Processing [4]
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 [6]
BH3-like motif-containing cell death inducer (BLID) OT479VJV BLID_HUMAN Gene/Protein Processing [3]
Bone morphogenetic protein 5 (BMP5) OTC0Y6E0 BMP5_HUMAN Gene/Protein Processing [3]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Gene/Protein Processing [7]
Cadherin-1 (CDH1) OTFJMXPM CADH1_HUMAN Gene/Protein Processing [8]
cAMP-dependent protein kinase type II-beta regulatory subunit (PRKAR2B) OTZEXEFH KAP3_HUMAN Post-Translational Modifications [3]
Catenin beta-1 (CTNNB1) OTZ932A3 CTNB1_HUMAN Post-Translational Modifications [9]
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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 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.
4 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.
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 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.
7 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.
8 Microcystin-LR promotes epithelial-mesenchymal transition in colorectal cancer cells through PI3-K/AKT and SMAD2. Toxicol Lett. 2017 Jan 4;265:53-60. doi: 10.1016/j.toxlet.2016.11.004. Epub 2016 Nov 14.
9 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.