(2S,3S,4S,5R,6S)-6-{[(1S,5R,13R,14S,17R)-14-(acetyloxy)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-10-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 159374
• Molecular Formular: C25H29NO10
• Molecular Mass: 503.49846
• Monoisotopic Mass: 503.17914613
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@H]4[C@@]3([C@H]([C@H](C=C4)OC(=O)C)O2)CCN1C)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O
• Canonical SMILES: CC(=O)O[C@H]1C=C[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C25H29NO10/c1-10(27)33-15-6-4-12-13-9-11-3-5-14(20-16(11)25(12,22(15)35-20)7-8-26(13)2)34-24-19(30)17(28)18(29)21(36-24)23(31)32/h3-6,12-13,15,17-19,21-22,24,28-30H,7-9H2,1-2H3,(H,31,32)/t12-,13+,15-,17-,18-,19+,21-,22-,24+,25-/m0/s1
• InChIKey: YVGOKLDIYZEHHQ-DSPHSEFCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-{[(1S,5R,13R,14S,17R)-14-(acetyloxy)-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]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-{[(1S,5R,13R,14S,17R)-14-(acetyloxy)-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]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (5α,6α)-6-(Acetyloxy)-7,8-didehydro-4,5-epoxy-17-methylmorphinan-3-yl β-D-Glucopyranosiduronic Acid; 6-Acetylmorphine 3-Glucuronide; Morphine 6-Acetate 3-Glucuronide; 6-Acetylmorphine 3-O-β-D-Glucuronide

Database IDs

• CAS Number: 62299-26-7
• PubChem SID: 162253509
• PubChem CID: 71312957

CALCULATED PROPERTIES

• Acid pKa: 2.65812
• H Acceptors: 10
• H Donor: 4
• LogD (pH = 5.5): -3.040997
• LogD (pH = 7.4): -3.0469224
• Log P: -3.0408218
• Molar Refractivity: 121.2857 cm^3
• Polarizability: 48.27294 Å^3
• Polar Surface Area: 155.22 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A186905

6-Acetylmorphine 3-O-β-D-Glucuronide is the glucuronide conjugate of 6-Acetyl Morphine (A186900 and a metabolite of Heroin (H281180).

REFERENCES

• Yeh, S.Y. et al.: J. Pharmac. Sci., 66, 201 (1977)
• Crews, B. et al.: Therap. Drug. Mon., 31, 749 (1977)