(1S,5R,13R,14S,17R)-14-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-10-yl acetate

• ChemBase ID: 125402
• Molecular Formular: C19H21NO4
• Molecular Mass: 327.37434
• Monoisotopic Mass: 327.14705816
• SMILES: CC(=O)Oc1c2c3c(C[C@@H]4[C@H]5[C@]3(CCN4C)[C@@H](O2)[C@H](C=C5)O)cc1
• Canonical SMILES: CC(=O)Oc1ccc2c3c1O[C@@H]1[C@@]43CCN([C@H](C2)[C@@H]4C=C[C@@H]1O)C
• InChI: InChI=1S/C19H21NO4/c1-10(21)23-15-6-3-11-9-13-12-4-5-14(22)18-19(12,7-8-20(13)2)16(11)17(15)24-18/h3-6,12-14,18,22H,7-9H2,1-2H3/t12-,13+,14-,18-,19-/m0/s1
• InChIKey: GMLREHXYJDLZOU-LEPYJNQMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14S,17R)-14-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraen-10-yl acetate
• IUPAC Traditional name: 3-monoacetylmorphine
• Synonyms: 3-Acetylmorphine; O(3)-monoacetylmorphine; 3-Monoacetylmorphine

Database IDs

• CAS Number: 5140-28-3
• PubChem SID: 162219752
• PubChem CID: 5462504
• Chemspider ID: 4575431
• Wikipedia Title: 3-Monoacetylmorphine

CALCULATED PROPERTIES

• Acid pKa: 13.782737
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -2.1511943
• LogD (pH = 7.4): -0.6206974
• Log P: 1.1078836
• Molar Refractivity: 89.2739 cm^3
• Polarizability: 34.53174 Å^3
• Polar Surface Area: 59.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Admin Routes: Intravenous
• Legal Status: Class A (UK); S9 (Australia); Schedule I (US)