(5R,8S,11R,12R,15S,18S,19S,22R)-15-(3-carbamimidamidopropyl)-8-[(4-hydroxyphenyl)methyl]-18-[(5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,5,12,19-tetramethyl-2-methylidene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid

• ChemBase ID: 154448
• Molecular Formular: C52H72N10O13
• Molecular Mass: 1045.18728
• Monoisotopic Mass: 1044.52803241
• 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)Cc1ccc(cc1)O)C(=O)O)C)CCCNC(=N)N)/C=C/C(=C\[C@H](C)[C@H](Cc1ccccc1)OC)/C
• Canonical SMILES: CO[C@H]([C@H](/C=C(\C=C\[C@@H]1NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](C)[C@@H](NC(=O)[C@H](Cc2ccc(cc2)O)NC(=O)[C@H](NC(=O)C(=C)N(C(=O)CC[C@H](NC(=O)[C@H]1C)C(=O)O)C)C)C(=O)O)/C)C)Cc1ccccc1
• InChI: InChI=1S/C52H72N10O13/c1-28(25-29(2)41(75-8)27-34-13-10-9-11-14-34)16-21-37-30(3)44(65)59-39(50(71)72)22-23-42(64)62(7)33(6)47(68)56-32(5)46(67)60-40(26-35-17-19-36(63)20-18-35)49(70)61-43(51(73)74)31(4)45(66)58-38(48(69)57-37)15-12-24-55-52(53)54/h9-11,13-14,16-21,25,29-32,37-41,43,63H,6,12,15,22-24,26-27H2,1-5,7-8H3,(H,56,68)(H,57,69)(H,58,66)(H,59,65)(H,60,67)(H,61,70)(H,71,72)(H,73,74)(H4,53,54,55)/t29-,30-,31+,32+,37-,38-,39+,40-,41-,43+/m0/s1
• InChIKey: OWHASZQTEFAUJC-NOEZPATISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R,8S,11R,12R,15S,18S,19S,22R)-15-(3-carbamimidamidopropyl)-8-[(4-hydroxyphenyl)methyl]-18-[(5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,5,12,19-tetramethyl-2-methylidene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid
• IUPAC Traditional name: (5R,8S,11R,12R,15S,18S,19S,22R)-15-(3-carbamimidamidopropyl)-8-[(4-hydroxyphenyl)methyl]-18-[(5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,5,12,19-tetramethyl-2-methylidene-3,6,9,13,16,20,25-heptaoxo-1,4,7,10,14,17,21-heptaazacyclopentacosane-11,22-dicarboxylic acid
• Synonyms: Microcystin YR from Microcystis aeruginosa

Database IDs

• CAS Number: 101064-48-6
• MDL Number: MFCD00236437
• PubChem SID: 162248587; 24896901
• PubChem CID: 71311866

CALCULATED PROPERTIES

• Acid pKa: 3.0606902
• H Acceptors: 16
• H Donor: 12
• LogD (pH = 5.5): -2.8138323
• LogD (pH = 7.4): -4.3045073
• Log P: -1.2787741
• Molar Refractivity: 286.5008 cm^3
• Polarizability: 106.03055 Å^3
• Polar Surface Area: 360.87 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble; ethanol: soluble; methanol: soluble2 mg/mL ((further dilute to 10% (v/v) methanol))
• Apperance: white powder

Safety Information

• RTECS: GT4010000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 26/27/28-36/37/38-43
• Safety Statements: 26-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H315-H317-H319-H330-H335
• GHS Precautionary statements: P260-P264-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 1
• Storage Temperature: -20°C

Product Information

• Empirical Formula (Hill Notation): C52H72N10O13

DETAILS

Sigma Aldrich - M4069

Biochem/physiol Actions
Microcystin YR inhibits protein phosphatase type 2A and protein phosphatase type 1. Toxicity to undifferentiated cells was seen by inhibition of neutral red uptake, >80% at 100 μM, after 48 h.1