(1S,17S,18S,19S)-5,7-dioxa-12-azapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-2(10),3,8,15-tetraene-17,18-diol hydrochloride

• ChemBase ID: 118999
• Molecular Formular: C16H18ClNO4
• Molecular Mass: 323.77142
• Monoisotopic Mass: 323.09243574
• SMILES: [C@H]12c3c(CN4[C@@H]1C(=C[C@@H]([C@H]2O)O)CC4)cc1c(c3)OCO1.Cl
• Canonical SMILES: O[C@H]1C=C2CCN3[C@H]2[C@@H]([C@@H]1O)c1cc2OCOc2cc1C3.Cl
• InChI: InChI=1S/C16H17NO4.ClH/c18-11-3-8-1-2-17-6-9-4-12-13(21-7-20-12)5-10(9)14(15(8)17)16(11)19;/h3-5,11,14-16,18-19H,1-2,6-7H2;1H/t11-,14-,15+,16+;/m0./s1
• InChIKey: VUVNTYCHKZBOMV-NVJKKXITSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,17S,18S,19S)-5,7-dioxa-12-azapentacyclo[10.6.1.0^2,^1^0.0^4,^8.0^1^5,^1^9]nonadeca-2(10),3,8,15-tetraene-17,18-diol hydrochloride; (1S,17S,18S,19S)-5,7-dioxa-12-azapentacyclo[10.6.1.0^2,^1^0.0^4,^8.0^1^5,^1^9]nonadeca-2,4(8),9,15-tetraene-17,18-diol hydrochloride
• IUPAC Traditional name: lycorine hydrochloride
• Synonyms: (1S,2S,3a1S,12bS)-2,3a1,4,5,7,12b-hexahydro-1H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-1,2-diol hydrochloride; Lycorine hydrochloride

Database IDs

• CAS Number: 2188-68-3
• MDL Number: MFCD00243111
• PubChem SID: 162107246; 24896395
• PubChem CID: 164943

CALCULATED PROPERTIES

• Acid pKa: 13.459855
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -2.21449
• LogD (pH = 7.4): -0.46332246
• Log P: 0.16233382
• Molar Refractivity: 76.1816 cm^3
• Polarizability: 29.64153 Å^3
• Polar Surface Area: 62.16 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: powder

Safety Information

• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (TLC)
• Salt Data: HCl
• Empirical Formula (Hill Notation): C16H17NO4 · HCl

DETAILS

Sigma Aldrich - L5139

Caution
Protect from light.
Biochem/physiol Actions
A selective inhibitor of peptidyl transferase center (PTC). In HL-60 (leukemia) cells, lycorine arrests the cell cycle at G2/M and induces apoptosis by a caspase-mediated pathway.1