(1R,10R,11S,12S,14R,19S,23R,25R)-1,10,11,12,14,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosan-22-yl 3,4-dimethoxybenzoate

• ChemBase ID: 132997
• Molecular Formular: C36H51NO11
• Molecular Mass: 673.79024
• Monoisotopic Mass: 673.34621146
• SMILES: CC1CCC2[C@@]([C@]3([C@H](C[C@]4(C5CCC6[C@]7([C@]5(C[C@]4(C3CN2C1)O)O[C@@]6(C(CC7)OC(=O)c1ccc(c(c1)OC)OC)O)C)O)O)O)(C)O
• Canonical SMILES: COc1ccc(cc1OC)C(=O)OC1CC[C@]2(C3[C@]1(O)O[C@]12C[C@@]2([C@@](C1CC3)(O)C[C@@H]([C@]1(C2CN2CC(C)CCC2[C@@]1(C)O)O)O)O)C
• InChI: InChI=1S/C36H51NO11/c1-19-6-11-26-31(3,40)35(43)25(17-37(26)16-19)33(42)18-34-24(32(33,41)15-27(35)38)10-9-23-30(34,2)13-12-28(36(23,44)48-34)47-29(39)20-7-8-21(45-4)22(14-20)46-5/h7-8,14,19,23-28,38,40-44H,6,9-13,15-18H2,1-5H3/t19?,23?,24?,25?,26?,27-,28?,30-,31+,32+,33+,34+,35-,36-/m0/s1
• InChIKey: FVECELJHCSPHKY-FCSYLLAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,10R,11S,12S,14R,19S,23R,25R)-1,10,11,12,14,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^2,^1^1.0^4,^9.0^1^5,^2^5.0^1^8,^2^3.0^1^9,^2^5]hexacosan-22-yl 3,4-dimethoxybenzoate; (1R,10R,11S,12S,14R,19S,23S,25R)-1,10,11,12,14,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^2,^1^1.0^4,^9.0^1^5,^2^5.0^1^8,^2^3.0^1^9,^2^5]hexacosan-22-yl 3,4-dimethoxybenzoate
• IUPAC Traditional name: (1R,10R,11S,12S,14R,19S,23R,25R)-1,10,11,12,14,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^2,^1^1.0^4,^9.0^1^5,^2^5.0^1^8,^2^3.0^1^9,^2^5]hexacosan-22-yl 3,4-dimethoxybenzoate; (1R,10R,11S,12S,14R,19S,23S,25R)-1,10,11,12,14,23-hexahydroxy-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.0^2,^1^1.0^4,^9.0^1^5,^2^5.0^1^8,^2^3.0^1^9,^2^5]hexacosan-22-yl 3,4-dimethoxybenzoate
• Synonyms: 3-Veratroylveracevine; Veratridine

Database IDs

• CAS Number: 71-62-5
• EC Number: 200-758-4
• MDL Number: MFCD00082515
• Beilstein Number: 78875
• PubChem SID: 162227274; 24900756
• PubChem CID: 6610253

CALCULATED PROPERTIES

• Acid pKa: 10.876727
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -2.2446074
• LogD (pH = 7.4): -0.5609655
• Log P: 0.82686615
• Molar Refractivity: 170.5108 cm^3
• Polarizability: 68.63466 Å^3
• Polar Surface Area: 178.61 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: ethanol: soluble50 mg/mL; ethanol: soluble50 mg/mL, clear, yellow
• Apperance: white to off-white powder

Safety Information

• RTECS: YX5600000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1
• Risk Statements: 26/27/28-36/37/38-48/20-52/53-62
• Safety Statements: 26-28-36/37-45-61
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H315-H319-H330-H335-H361-H373-H412
• GHS Precautionary statements: P260-P264-P273-P280-P284-P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges; 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 1544 6.1/PG 1
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC); ≥90% (TLC)
• Impurities: ≤5% solvents
• Empirical Formula (Hill Notation): C36H51NO11

DETAILS

Sigma Aldrich - V5754

Biochem/physiol Actions
Opens voltage-dependent Na+ channels and prevents their inactivation. This, in turn, opens voltage-activated calcium channels, thus increasing intracellular calcium content and inducing neurotransmitter release. Alkaloid neurotoxin which depolarizes excitable tissue; used to increase membrane sodium permeability. Veratridine is cytotoxic to chromaffin cells in vitro.

Sigma Aldrich - V109

Biochem/physiol Actions
Opens voltage-dependent Na+ channels and prevents their inactivation. This, in turn, opens voltage-activated calcium channels, thus increasing intracellular calcium content and inducing neurotransmitter release. Alkaloid neurotoxin which depolarizes excitable tissue; used to increase membrane sodium permeability. Veratridine is cytotoxic to chromaffin cells in vitro.

Sigma Aldrich - 94838

Biochem/physiol Actions
Opens voltage-dependent Na+ channels and prevents their inactivation. This, in turn, opens voltage-activated calcium channels, thus increasing intracellular calcium content and inducing neurotransmitter release. Alkaloid neurotoxin which depolarizes excitable tissue; used to increase membrane sodium permeability. Veratridine is cytotoxic to chromaffin cells in vitro.