Microcystin-LR (MCYST-LR) - Moligand™, ~10ug/ml in Methanol/Water(1/1) , CAS No.101043-37-2

CAS: 101043-37-2 Cat. No.: M299661 Molecular Weight: 995.17 EC Number: 621-323-9

GRADE & PURITY Moligand™, ~10ug/ml in Methanol/Water(1/1)

Synonyms

Cyanoginosin LR | Toxin-LR | Toxin I (Microcystis aeruginosa)

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Product introduction：

Microcystins are toxic molecules produced by cyanobacterial blooms due to water eutrophication. Microcystin-LR proves to be a potent inhibitor of type 1 (IC50=1.7 nM) and type 2A (IC50= 0.04 nM) protein phosphatases. Microcystin-LR inhibits the activity of both type 1 and type 2A phosphatases >10-fold more potently than okadaic acid under the same conditions. Type 2A protein phosphatases in dilute mammalian cell extracts are found to be completely inhibited by 0.5 nM microcystin-LR while type 1 protein phosphatases are only slightly affected at this concentration.

Application：

Microcystin-LR may be used as an analytical reference standard for the determination of the analyte in surface water samples using high-performance liquid chromatography coupled to tandem mass spectrometry with electrospray ionization source (HPLC-ESI-MS/MS).

Specifications

Synonyms

Cyanoginosin LR | Toxin-LR | Toxin I (Microcystis aeruginosa)

Specifications & Purity

Moligand™, ~10ug/ml in Methanol/Water(1/1)

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Names and Identifiers

• Canonical Smiles: CC1C(NC(=O)C(NC(=O)C(C(NC(=O)C(NC(=O)C(NC(=O)C(=C)N(C(=O)CCC(NC1=O)C(=O)O)C)C)CC(C)C)C(=O)O)C)CCCN=C(N)N)C=CC(=CC(C)C(CC2=CC=CC=C2)OC)C
• 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
• InChIKey: ZYZCGGRZINLQBL-GWRQVWKTSA-N
• 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
• Isomeric 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
• WGK Germany: WGK 2
• Alternate CAS: 101043-37-2
• NSC Number: 733608
• MeSH Entry Terms: cyanoginosin LR;cyanoginosin-lr;cyclo(2,3-didehydro-n-methylalanyl-D-alanyl-l-leucyl-erythro-3-methyl-D-beta-aspartyl-l-arginyl-(2S,3S,4E,6E,8S,9S)-4,5,6,7-tetradehydro-9-methoxy-2,6,8-trimethyl-10-phenyl-3-aminodecanoyl-d-gamma-glutamyl);cyclo(Ala-Leu-MA
• Molecular Weight: 995.17
• Reaxy-Rn: 30146673
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=30146673&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Peptidomimetics
      • Subclass Hybrid peptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Peptidomimetics
• Subclass: Hybrid peptides
• Intermediate Tree Nodes: Not available
• Direct Parent: Hybrid peptides
• Alternative Parents: Oligopeptides Macrolactams Beta amino acids and derivatives Alpha amino acids and derivatives Benzene and substituted derivatives Dicarboxylic acids and derivatives Tertiary carboxylic acid amides Secondary carboxylic acid amides Guanidines Lactams Dialkyl ethers Carboxylic acids Carboximidamides Azacyclic compounds Propargyl-type 1,3-dipolar organic compounds Organic oxides Carbonyl compounds Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Cyclic hybrid peptide - Alpha-oligopeptide - Macrolactam - Beta amino acid or derivatives - Alpha-amino acid or derivatives - Monocyclic benzene moiety - Dicarboxylic acid or derivatives - Benzenoid - Tertiary carboxylic acid amide - Carboxamide group - Guanidine - Lactam - Secondary carboxylic acid amide - Carboxylic acid derivative - Carboxylic acid - Dialkyl ether - Ether - Azacycle - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Carboximidamide - Hydrocarbon derivative - Organopnictogen compound - Carbonyl group - Organic oxide - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Organic oxygen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
• External Descriptors: Microcystins

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

PPM1A Tchem Protein phosphatase 1A (1 Activities)

Discover Target: PPM1A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PTPN1 Tchem Tyrosine-protein phosphatase non-receptor type 1 (2 Activities)

Discover Target: PTPN1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PPP2R5A Tchem Serine/threonine-protein phosphatase 2A 56 kDa regulatory subunit alpha isoform (1 Activities)

Discover Target: PPP2R5A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PPP2R2A Tchem Serine/threonine-protein phosphatase 2A 55 kDa regulatory subunit B alpha isoform (1 Activities)

Discover Target: PPP2R2A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PPP1CC Tchem Serine/threonine-protein phosphatase PP1-gamma catalytic subunit (10 Activities)

Discover Target: PPP1CC

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PPP2R5A Tchem Serine/threonine protein phosphatase 2A, 56 kDa regulatory subunit, alpha isoform (8 Activities)

Discover Target: PPP2R5A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PPM1A Tchem Protein phosphatase 2C alpha (38 Activities)

Discover Target: PPM1A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PPP2R2A Tchem Serine/threonine protein phosphatase 2A, 55 kDa regulatory subunit B, alpha isoform (8 Activities)

Discover Target: PPP2R2A

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PPP1CC Tchem Serine/threonine protein phosphatase PP1-gamma catalytic subunit (63 Activities)

Discover Target: PPP1CC

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

A549 (127892 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HCT-116 (91556 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1A2 Tchem Solute carrier organic anion transporter family member 1A2 (104 Activities)

Discover Target: SLCO1A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO2B1 Tchem Solute carrier organic anion transporter family member 2B1 (580 Activities)

Discover Target: SLCO2B1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

Discover Target: Ptpn1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Serine-threonine protein phosphatase 2A regulatory subunit (96 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mus musculus (284745 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NIH3T3 (5395 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slco1a1 Solute carrier organic anion transporter family member 1A1 (265 Activities)

Discover Target: Slco1a1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slco1a4 Solute carrier organic anion transporter family member 1A4 (114 Activities)

Discover Target: Slco1a4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slco1b2 Solute carrier organic anion transporter family member 1B2 (36 Activities)

Discover Target: Slco1b2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: heat sensitive
• Molecular Weight: 995.200 g/mol
• XLogP3: 2.300
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 15
• Exact Mass: 994.549 Da
• Monoisotopic Mass: 994.549 Da
• Topological Polar Surface Area: 343.000 Ų
• Heavy Atom Count: 71
• Formal Charge: 0
• Complexity: 2000.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 10
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 2
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 2
• Covalently-Bonded Unit Count: 1