6-Acetylmorphine

Details

• Internal ID: 4c01e94d-7c95-4b8a-8705-791edc867582
• Taxonomy: Alkaloids and derivatives > Morphinans
• IUPAC Name: [(4R,4aR,7S,7aR,12bS)-9-hydroxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] acetate
• InChI: InChI=1S/C19H21NO4/c1-10(21)23-15-6-4-12-13-9-11-3-5-14(22)17-16(11)19(12,18(15)24-17)7-8-20(13)2/h3-6,12-13,15,18,22H,7-9H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1
• InChI Key: JJGYGPZNTOPXGV-SSTWWWIQSA-N
• Popularity: 399 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.40 g/mol
• Exact Mass: 327.14705815 g/mol
• Topological Polar Surface Area (TPSA): 59.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.77
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 6-O-Monoacetylmorphine
• 2784-73-8
• 6-MAM
• 6-O-Acetylmorphine
• M5E47P1ZCH
• DTXSID60182154
• 6-Monoacetylmorphine
• morphine-6-acetate
• 6-MAM cpd
• 6-(0-acetyl)morphine
• RefChem:540029
• DTXCID70104645
• ((4R,4aR,7S,7aR,12bS)-9-hydroxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinoline-7-yl) acetate
• Monoacetylmorphine
• O(sup 6)-Monoacetylmorphine
• Morphine 6-acetate
• 6-Acetyl Morphine
• O6-Monoacetylmorphine
• CHEBI:2168
• 7,8-Didehydro-4,5alpha-epoxy-17-methylmorphinan-3,6alpha-diol 6-acetate
• Morphinan-3,6-alpha-diol, 7,8-didehydro-4,5-alpha-epoxy-17-methyl-, 6-acetate
• Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl-, (5alpha,6alpha)-, 6-acetate
• 6-Acetyl Morphine (1.0mg/ml in Acetonitrile)
• 6-Acetyl Morphine (100 ug/mL in Acetonitrile)
• UNII-M5E47P1ZCH
• O6-Acetylmorphine
• 6-monoaceylmorphine
• Heroin-M 6-MAM
• CHEMBL592009
• SCHEMBL7940016
• SCHEMBL27832558
• Morphine 6-acetate (6CI,7CI)
• BDBM224020
• Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl- (5.alpha.,6.alpha.)-, 6-acetate
• PD017203
• 6-Acetylmorphine 0.1 mg/ml in Acetonitrile
• 6-Acetylmorphine 1.0 mg/ml in Acetonitrile
• NS00000049
• Q2406967
• morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl-, 6-acetate, (5alpha,6alpha)-
• Morphinan-3,6alpha-diol, 7,8-didehydro-4,5alpha-epoxy-17-methyl-, 6-acetate (8CI)
• [(4R,4aR,7S,7aR,12bS)-9-hydroxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] acetate
• YMorphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-methyl- (5alpha,6alpha)-, 6-acetate (9CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9722	97.22%
Caco-2	+	0.7522	75.22%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	-	0.9286	92.86%
Subcellular localzation	Mitochondria	0.4983	49.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9277	92.77%
OATP1B3 inhibitior	+	0.9375	93.75%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.6836	68.36%
P-glycoprotein inhibitior	-	0.6950	69.50%
P-glycoprotein substrate	+	0.8424	84.24%
CYP3A4 substrate	+	0.7492	74.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3586	35.86%
CYP3A4 inhibition	-	0.8160	81.60%
CYP2C9 inhibition	-	0.8846	88.46%
CYP2C19 inhibition	-	0.8197	81.97%
CYP2D6 inhibition	+	0.5901	59.01%
CYP1A2 inhibition	-	0.7958	79.58%
CYP2C8 inhibition	-	0.9464	94.64%
CYP inhibitory promiscuity	-	0.8366	83.66%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6494	64.94%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9761	97.61%
Skin irritation	-	0.7930	79.30%
Skin corrosion	-	0.9478	94.78%
Ames mutagenesis	-	0.7254	72.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6525	65.25%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	-	0.8375	83.75%
skin sensitisation	-	0.8214	82.14%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.6786	67.86%
Acute Oral Toxicity (c)	III	0.6652	66.52%
Estrogen receptor binding	-	0.5000	50.00%
Androgen receptor binding	-	0.7219	72.19%
Thyroid receptor binding	+	0.6024	60.24%
Glucocorticoid receptor binding	+	0.5546	55.46%
Aromatase binding	-	0.7537	75.37%
PPAR gamma	-	0.4911	49.11%
Honey bee toxicity	-	0.7415	74.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6150	61.50%
Fish aquatic toxicity	+	0.9541	95.41%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.37%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.53%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.60%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.16%	95.56%
CHEMBL236	P41143	Delta opioid receptor	90.25%	99.35%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.37%	95.89%
CHEMBL217	P14416	Dopamine D2 receptor	86.72%	95.62%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.42%	97.25%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.24%	93.04%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.12%	86.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.77%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.68%	91.19%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.04%	99.23%
CHEMBL233	P35372	Mu opioid receptor	82.14%	97.93%
CHEMBL5028	O14672	ADAM10	81.22%	97.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.14%	94.00%

Plants that contains it

• Papaver somniferum

Cross-Links

• PubChem: 5462507
• NPASS: NPC43726