2-[34-(butan-2-yl)-13-(3,4-dihydroxybutan-2-yl)-8,22-dihydroxy-2,5,11,14,27,30,33,36,39-nonaoxo-27λ4-thia-3,6,12,15,25,29,32,35,38-nonaazapentacyclo[14.12.11.06,10.018,26.019,24]nonatriaconta-18(26),19,21,23-tetraen-4-yl]acetic acid

• ChemBase ID: 132326
• Molecular Formular: C39H53N9O15S
• Molecular Mass: 919.95442
• Monoisotopic Mass: 919.33818304
• SMILES: CCC(C)C1C(=O)NCC(=O)NC2CS(=O)c3c(c4ccc(cc4[nH]3)O)CC(C(=O)NCC(=O)N1)NC(=O)C(NC(=O)C1CC(CN1C(=O)C(NC2=O)CC(=O)O)O)C(C)C(CO)O
• Canonical SMILES: OCC(C(C1NC(=O)C2CC(CN2C(=O)C(CC(=O)O)NC(=O)C2CS(=O)c3c(CC(NC1=O)C(=O)NCC(=O)NC(C(CC)C)C(=O)NCC(=O)N2)c1ccc(cc1[nH]3)O)O)C)O
• InChI: InChI=1S/C39H53N9O15S/c1-4-16(2)31-36(60)41-11-28(53)42-25-15-64(63)38-21(20-6-5-18(50)7-22(20)45-38)9-23(33(57)40-12-29(54)46-31)43-37(61)32(17(3)27(52)14-49)47-35(59)26-8-19(51)13-48(26)39(62)24(10-30(55)56)44-34(25)58/h5-7,16-17,19,23-27,31-32,45,49-52H,4,8-15H2,1-3H3,(H,40,57)(H,41,60)(H,42,53)(H,43,61)(H,44,58)(H,46,54)(H,47,59)(H,55,56)
• InChIKey: IEQCUEXVAPAFMQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[34-(butan-2-yl)-13-(3,4-dihydroxybutan-2-yl)-8,22-dihydroxy-2,5,11,14,27,30,33,36,39-nonaoxo-27λ^4-thia-3,6,12,15,25,29,32,35,38-nonaazapentacyclo[14.12.11.0^6,^1^0.0^1^8,^2^6.0^1^9,^2^4]nonatriaconta-18(26),19,21,23-tetraen-4-yl]acetic acid
• IUPAC Traditional name: β-amanitin
• Synonyms: β-Amanitin from Amanita phalloides

Database IDs

• CAS Number: 21150-22-1
• EC Number: 244-244-8
• MDL Number: MFCD00151212
• PubChem SID: 162226603; 24890528
• PubChem CID: 2276

CALCULATED PROPERTIES

• Acid pKa: 3.646986
• H Acceptors: 15
• H Donor: 13
• LogD (pH = 5.5): -8.704401
• LogD (pH = 7.4): -10.184677
• Log P: -6.854337
• Molar Refractivity: 219.4847 cm^3
• Polarizability: 87.1496 Å^3
• Polar Surface Area: 375.09 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: NJ8324000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 26/27/28
• Safety Statements: 7-28-36/37/39-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• GHS Precautionary statements: P260-P264-P280-P284-P302 + P350-P310
• RID/ADR: UN 3462 6.1/PG 1
• Storage Temperature: -20°C

Product Information

• Purity: ~90% (HPLC)

DETAILS

Sigma Aldrich - A1304

Biochem/physiol Actions
Toxic constituent of the mushroom, Amanita phalloides, inhibits eukaryotic RNA polymerase II and III, but not RNA polymerase I or bacterial RNA polymerase. Inhibits mammalian protein synthesis.