(1S,4S,5R,6S,8R,9R,10S,13S,16S)-8,9,16-trihydroxy-11-(hydroxymethyl)-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.12,5.01,10.03,8.013,17]nonadecan-4-yl acetate

• ChemBase ID: 155633
• Molecular Formular: C24H37NO8
• Molecular Mass: 467.55248
• Monoisotopic Mass: 467.25191715
• SMILES: CC(=O)O[C@H]1[C@@H]2CC3C1[C@](C[C@@H]2OC)([C@]1(CC2[C@@]43[C@@H]1N(C[C@@]2(CC[C@@H]4O)COC)CO)O)O
• Canonical SMILES: COC[C@]12CC[C@@H]([C@@]34C2C[C@]([C@H]3N(C1)CO)(O)[C@@]1(C2C4C[C@@H]([C@@H]2OC(=O)C)[C@H](C1)OC)O)O
• InChI: InChI=1S/C24H37NO8/c1-12(27)33-19-13-6-14-18(19)22(29,7-15(13)32-3)23(30)8-16-21(10-31-2)5-4-17(28)24(14,16)20(23)25(9-21)11-26/h13-20,26,28-30H,4-11H2,1-3H3/t13-,14?,15+,16?,17+,18?,19+,20-,21+,22-,23-,24-/m1/s1
• InChIKey: NIKWMQWPEFMBIP-FVZLDLTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,5R,6S,8R,9R,10S,13S,16S)-8,9,16-trihydroxy-11-(hydroxymethyl)-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^2,^5.0^1,^1^0.0^3,^8.0^1^3,^1^7]nonadecan-4-yl acetate
• IUPAC Traditional name: (1S,4S,5R,6S,8R,9R,10S,13S,16S)-8,9,16-trihydroxy-11-(hydroxymethyl)-6-methoxy-13-(methoxymethyl)-11-azahexacyclo[7.7.2.1^2,^5.0^1,^1^0.0^3,^8.0^1^3,^1^7]nonadecan-4-yl acetate
• Synonyms: 14-Acetylvirescenine from Delphinium sp.

Database IDs

• MDL Number: MFCD00274515
• PubChem SID: 24891091; 162249771
• PubChem CID: 16218945

CALCULATED PROPERTIES

• Acid pKa: 12.849854
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -4.576837
• LogD (pH = 7.4): -2.829254
• Log P: -2.219997
• Molar Refractivity: 115.0328 cm^3
• Polarizability: 46.851433 Å^3
• Polar Surface Area: 128.92 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: white powder

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99% (TLC)
• Empirical Formula (Hill Notation): C25H39NO7

DETAILS

Sigma Aldrich - A6472

Biochem/physiol Actions
Blocks the propagation of the action potential at the nicotinic cholinoreceptors of vegetative ganglia and neuro-muscular junctions. Hypotensive and curare-like action, I.V. and orally.
Warning
Protect from light.
Application
14-Acetylvirescenine blocks action potential propagation at the nicotinic receptors of vegetative ganglia and neuromuscular junctions. 14-Acetylvirescenine is hypotensive with curare-like activity.