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]acetamide

• ChemBase ID: 134142
• Molecular Formular: C39H54N10O14S
• Molecular Mass: 918.96966
• Monoisotopic Mass: 918.35416746
• 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)N)O)C(C)C(CO)O
• Canonical SMILES: OCC(C(C1NC(=O)C2CC(CN2C(=O)C(CC(=O)N)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/C39H54N10O14S/c1-4-16(2)31-36(60)42-11-29(55)43-25-15-64(63)38-21(20-6-5-18(51)7-22(20)46-38)9-23(33(57)41-12-30(56)47-31)44-37(61)32(17(3)27(53)14-50)48-35(59)26-8-19(52)13-49(26)39(62)24(10-28(40)54)45-34(25)58/h5-7,16-17,19,23-27,31-32,46,50-53H,4,8-15H2,1-3H3,(H2,40,54)(H,41,57)(H,42,60)(H,43,55)(H,44,61)(H,45,58)(H,47,56)(H,48,59)
• InChIKey: CIORWBWIBBPXCG-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]acetamide
• IUPAC Traditional name: α-amanitin
• Synonyms: α-Amanitin

Database IDs

• CAS Number: 23109-05-9
• EC Number: 245-432-2
• MDL Number: MFCD00215842
• Beilstein Number: 1071138
• PubChem SID: 24890639; 162228419
• PubChem CID: 2100

CALCULATED PROPERTIES

• Acid pKa: 9.375075
• H Acceptors: 14
• H Donor: 13
• LogD (pH = 5.5): -7.6613355
• LogD (pH = 7.4): -7.6657
• Log P: -7.6612797
• Molar Refractivity: 221.3069 cm^3
• Polarizability: 87.80125 Å^3
• Polar Surface Area: 380.88 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble1.0 mg/mL
• Apperance: white to light yellow powder
• Melting Point: 254-255 °C(lit.)
• Absorption Wavelength: ε1M/310 nm, H2O 13,500

Safety Information

• RTECS: BD6195000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 3462
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 26/27/28-33
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330-H373
• 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; Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 3462 6.1/PG 2
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥90% (HPLC); ≥95.0% (HPLC)
• Biological Source: from Amanita phalloides
• Empirical Formula (Hill Notation): C39H54N10O14S

DETAILS

Sigma Aldrich - A2263

Amino Acid Sequence
Asn-Hyp-Hyi-Trp-Gly-Ile-Gly-Cys [Bridge: 4-8]
Caution
When stored frozen in the dark, retained samples were found to be greater than 99% by HPLC after two years.
Reconstitution
Store a 1 mg/ml aqueous stock solution frozen at -20°C. It does not degrade with repeated freeze-thaw cycles. Dilute into the appropriate buffer immediately prior to use. Product is destroyed by concentrated acid or base.
Biochem/physiol Actions
The major toxic constituent of the mushroom, Amanita phalloides, inhibits eukaryotic RNA polymerase II and III, but does not inhibit RNA polymerase I or bacterial RNA polymerase. Inhibits mammalian protein synthesis.

Sigma Aldrich - 06422

Amino Acid Sequence
Asn-Hyp-Hyi-Trp-Gly-Ile-Gly-Cys [Bridge: 4-8]
Biochem/physiol Actions
The major toxic constituent of the mushroom, Amanita phalloides, inhibits eukaryotic RNA polymerase II and III, but does not inhibit RNA polymerase I or bacterial RNA polymerase. Inhibits mammalian protein synthesis.