2-[28-(2,3-dihydroxy-2-methylpropyl)-18-hydroxy-23-methyl-15,21,24,26,29,32,35-heptaoxo-31-(propan-2-yl)-12-thia-10,16,22,25,27,30,33,36-octaazapentacyclo[12.11.11.03,11.04,9.016,20]hexatriaconta-3(11),4,6,8-tetraen-34-yl]-2-hydroxy-N-{2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]ethyl}acetamide

• ChemBase ID: 153093
• Molecular Formular: C45H57N13O15S
• Molecular Mass: 1052.07718
• Monoisotopic Mass: 1051.38177919
• SMILES: CC1C(=O)NC2Cc3c4ccccc4[nH]c3SCC(C(=O)N3CC(CC3C(=O)N1)O)NC(=O)C(NC(=O)C(NC(=O)C(NC2=O)CC(C)(CO)O)C(C)C)C(C(=O)NCCNc1ccc(c2c1non2)[N+](=O)[O-])O
• Canonical SMILES: OCC(CC1NC(=O)C2NC(=O)C(C)NC(=O)C3CC(CN3C(=O)C(CSc3c(C2)c2ccccc2[nH]3)NC(=O)C(NC(=O)C(NC1=O)C(C)C)C(C(=O)NCCNc1ccc(c2c1non2)[N+](=O)[O-])O)O)(O)C
• InChI: InChI=1S/C45H57N13O15S/c1-19(2)31-40(66)54-34(35(61)42(68)47-12-11-46-25-9-10-29(58(71)72)33-32(25)55-73-56-33)41(67)51-28-17-74-43-23(22-7-5-6-8-24(22)52-43)14-26(37(63)50-27(38(64)53-31)15-45(4,70)18-59)49-36(62)20(3)48-39(65)30-13-21(60)16-57(30)44(28)69/h5-10,19-21,26-28,30-31,34-35,46,52,59-61,70H,11-18H2,1-4H3,(H,47,68)(H,48,65)(H,49,62)(H,50,63)(H,51,67)(H,53,64)(H,54,66)
• InChIKey: VLODDNGPYAXAPW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[28-(2,3-dihydroxy-2-methylpropyl)-18-hydroxy-23-methyl-15,21,24,26,29,32,35-heptaoxo-31-(propan-2-yl)-12-thia-10,16,22,25,27,30,33,36-octaazapentacyclo[12.11.11.0^3,^1^1.0^4,^9.0^1^6,^2^0]hexatriaconta-3(11),4,6,8-tetraen-34-yl]-2-hydroxy-N-{2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]ethyl}acetamide
• IUPAC Traditional name: 2-[28-(2,3-dihydroxy-2-methylpropyl)-18-hydroxy-31-isopropyl-23-methyl-15,21,24,26,29,32,35-heptaoxo-12-thia-10,16,22,25,27,30,33,36-octaazapentacyclo[12.11.11.0^3,^1^1.0^4,^9.0^1^6,^2^0]hexatriaconta-3(11),4,6,8-tetraen-34-yl]-2-hydroxy-N-{2-[(7-nitro-2,1,3-benzoxadiazol-4-yl)amino]ethyl}acetamide
• Synonyms: N-(7-Nitrobenz-2-oxa-1,3-diazol-4-yl)phallacidin; NBD phallacidin; N-(7-Nitrobenzofurazan-4-yl)phallacidin

Database IDs

• CAS Number: 73413-78-2
• PubChem SID: 162247233
• PubChem CID: 4682184

CALCULATED PROPERTIES

• Acid pKa: 10.05232
• H Acceptors: 17
• H Donor: 13
• LogD (pH = 5.5): -4.771042
• LogD (pH = 7.4): -4.7718883
• Log P: -4.7710314
• Molar Refractivity: 259.0743 cm^3
• Polarizability: 101.2805 Å^3
• Polar Surface Area: 417.49 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Fluorescence: λex 464 nm; λem 536 nm in methanol

Safety Information

• 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
• Safety Statements: 28-36/37-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330
• 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

• Suitability: suitable for fluorescence
• Empirical Formula (Hill Notation): C45H57N13O15S

DETAILS

Sigma Aldrich - 11451

Other Notes
Probe for actin: In situ localization of actin filaments1; staining of F-actin2
Reconstitution
Reconstitution in 1.5 mL methanol will yield a ~6.6 μM stock solution. This stock solution is sufficient for 300 applications (dying of formaldehyde-fixed cells).