(5R,6S,9S,12S,13S,16R)-9-(3-carbamimidamidopropyl)-2-ethylidene-12-[(5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,6,13-trimethyl-3,7,10,14,19-pentaoxo-1,4,8,11,15-pentaazacyclononadecane-5,16-dicarboxylic acid

• ChemBase ID: 155573
• Molecular Formular: C41H60N8O10
• Molecular Mass: 824.9627
• Monoisotopic Mass: 824.44324016
• SMILES: C/C=C\1/C(=O)N[C@@H]([C@@H](C(=O)N[C@H](C(=O)N[C@H]([C@@H](C(=O)N[C@@H](CCC(=O)N1C)C(=O)O)C)/C=C/C(=C/[C@H](C)[C@H](Cc1ccccc1)OC)/C)CCCNC(=N)N)C)C(=O)O
• 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(=C/C)/N(C(=O)CC[C@H](NC(=O)[C@H]1C)C(=O)O)C)C(=O)O)\C)C)Cc1ccccc1
• InChI: InChI=1S/C41H60N8O10/c1-8-31-38(54)48-34(40(57)58)26(5)36(52)46-29(15-12-20-44-41(42)43)37(53)45-28(25(4)35(51)47-30(39(55)56)18-19-33(50)49(31)6)17-16-23(2)21-24(3)32(59-7)22-27-13-10-9-11-14-27/h8-11,13-14,16-17,21,24-26,28-30,32,34H,12,15,18-20,22H2,1-7H3,(H,45,53)(H,46,52)(H,47,51)(H,48,54)(H,55,56)(H,57,58)(H4,42,43,44)/t24-,25-,26-,28-,29-,30+,32-,34+/m0/s1
• InChIKey: IXBQSRWSVIBXNC-YBOPQVMDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R,6S,9S,12S,13S,16R)-9-(3-carbamimidamidopropyl)-2-ethylidene-12-[(5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,6,13-trimethyl-3,7,10,14,19-pentaoxo-1,4,8,11,15-pentaazacyclononadecane-5,16-dicarboxylic acid
• IUPAC Traditional name: (5R,6S,9S,12S,13S,16R)-9-(3-carbamimidamidopropyl)-2-ethylidene-12-[(5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,6,13-trimethyl-3,7,10,14,19-pentaoxo-1,4,8,11,15-pentaazacyclononadecane-5,16-dicarboxylic acid
• Synonyms: 1,4,8,11,15-Pentaazacyclononadecane, cyclic peptide; Nodularin; Cyclo[(2S,3S,4E,6E,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6-decadienoyl-D-γ-glutamyl-(2Z)-2-(methylamino)-2-butenoyl-(3S)-3-methyl-Dβ-aspartyl-L-arginyl); Nodularin solution; 节球毒素; 环[(2S,3S,4E,6E,8S,9S)-3-氨基-9-甲氧基-2,6,8-三甲基-10-苯基-4,6-癸二烯酰基-D-γ-谷氨酰基-(2Z)-2-(甲氨基)-2-丁烯酰基-(3S)-3-甲基-Dβ-天冬氨酰-L-精氨酰); 节球毒素 溶液

Database IDs

• CAS Number: 118399-22-7
• EC Number: 200-659-6
• MDL Number: MFCD16659855
• PubChem SID: 162249711
• PubChem CID: 14217092

CALCULATED PROPERTIES

• Acid pKa: 3.1089077
• H Acceptors: 13
• H Donor: 9
• LogD (pH = 5.5): -2.6592486
• LogD (pH = 7.4): -4.174611
• Log P: -1.183689
• Molar Refractivity: 230.9796 cm^3
• Polarizability: 84.15833 Å^3
• Polar Surface Area: 282.44 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: methanol: soluble2 mg/mL (Further dilute to 10% (v/v) methanol. Store solutions at -20°C for up to six months.)
• Flash Point: 11 °C; 51.8 °F

Safety Information

• RTECS: GU2294250
• European Hazard Symbols: Flammable (F); Toxic (T); Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 1; 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 11-23/24/25-39/23/24/25; 26/27/28-36/37/38-43
• Safety Statements: 26-36/37/39-45; 7-16-36/37-45
• GHS Pictograms: GHS02; GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H301 + H311 + H331-H370; H300 +H310 + H330-H315-H317-H319-H335
• GHS Precautionary statements: P210-P260-P280-P301 + P310-P311; P260-P264-P280-P284-P301 + P310-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: -20°C; 2-8°C

Product Information

• Concentration: 10 μg/mL in methanol
• Grade: analytical standard, for environmental analysis
• Empirical Formula (Hill Notation): C41H60N8O10

DETAILS

Sigma Aldrich - N5148

Biochem/physiol Actions
Potent inhibitor of protein phosphatases types 1 and 2A. Tumor promoter in experimental animal model.1; at higher doses, causes massive liver hemorrhage. Tumor-promoting effect is due to increasing oxidative stress, as evidenced by reduced levels of glutathione and appearance of oxidative damage in DNA bases.2