(2R,4R,5R)-2-{[(1S,4S,6R)-4,6-diamino-3-{[(2S)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol

• ChemBase ID: 177777
• Molecular Formular: C19H37N5O7
• Molecular Mass: 447.52638
• Monoisotopic Mass: 447.26929855
• SMILES: [C@@]1([C@@H](C([C@H](OC1)O[C@H]1[C@@H](C[C@@H](C(C1O)O[C@@H]1C(CC=C(O1)CN)N)N)N)O)NC)(O)C
• Canonical SMILES: NCC1=CCC([C@H](O1)OC1[C@@H](N)C[C@H]([C@@H](C1O)O[C@H]1OC[C@]([C@@H](C1O)NC)(C)O)N)N
• InChI: InChI=1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9?,10-,11+,12?,13?,14?,15-,16+,17+,18+,19-/m0/s1
• InChIKey: URWAJWIAIPFPJE-KPLNNWMXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4R,5R)-2-{[(1S,4S,6R)-4,6-diamino-3-{[(2S)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol
• IUPAC Traditional name: (2R,4R,5R)-2-{[(1S,4S,6R)-4,6-diamino-3-{[(2S)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy}-2-hydroxycyclohexyl]oxy}-5-methyl-4-(methylamino)oxane-3,5-diol
• Synonyms: (9α,13α,14α)-7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one Hydrochloride; 7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methyl-9α,13α,14α-morphinan-6-one Hydrochloride; (9α,13α,14α)- 7,8-Didehydro-4-hydroxy-3,7-dimethoxy-17-methylmorphinan-6-one Hydrochloride; Cucoline Hydrochloride; NSC 76021; Sinomenin Hydrochloride; Sinomenine Hydrochloride

Database IDs

• CAS Number: 6080-33-7
• PubChem SID: 164233687
• PubChem CID: 71752202

CALCULATED PROPERTIES

• Acid pKa: 12.548462
• H Acceptors: 12
• H Donor: 8
• LogD (pH = 5.5): -18.497313
• LogD (pH = 7.4): -11.9235935
• Log P: -4.3185678
• Molar Refractivity: 110.3207 cm^3
• Polarizability: 45.65683 Å^3
• Polar Surface Area: 213.72 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: >235°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - S487500

Sinomenine is an optical isomer of Methoxythebainone. Sinomenine was extracted from root of Sinomenium acutum. Sinomenine has anti-inflammatory and analgesic effect.

REFERENCES

• Kitasato, O., et al.: Arch. Exp. Med., 6, 259 (1925)
• Lodge, D., et al.: Eur. J. Pharmacol., 26, 277 (1925)