Benzylmorphine

Details

• Internal ID: 5f3a8733-6157-481a-a871-d3f755f40e31
• Taxonomy: Alkaloids and derivatives > Morphinans
• IUPAC Name: (4R,4aR,7S,7aR,12bS)-3-methyl-9-phenylmethoxy-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
• InChI: InChI=1S/C24H25NO3/c1-25-12-11-24-17-8-9-19(26)23(24)28-22-20(27-14-15-5-3-2-4-6-15)10-7-16(21(22)24)13-18(17)25/h2-10,17-19,23,26H,11-14H2,1H3/t17-,18+,19-,23-,24-/m0/s1
• InChI Key: RDJGWRFTDZZXSM-RNWLQCGYSA-N
• Popularity: 38 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₅NO₃
• Molecular Weight: 375.50 g/mol
• Exact Mass: 375.18344366 g/mol
• Topological Polar Surface Area (TPSA): 41.90 Ų
• XlogP: 2.60
• Atomic LogP (AlogP): 3.07
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• O3-Benzylmorphine
• Morphine, benzyl-
• 14297-87-1
• Peronine
• EINECS 238-230-0
• UNII-83C78V3OL9
• 83C78V3OL9
• 3-Benzyloxy-4,5alpha-epoxy-17-methyl-7-morphinen-6alpha-ol
• BENZYLMORPHINE [MI]
• IDS-NB-002
• DTXSID30162246
• Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-17-methyl-3-(phenylmethoxy)-, (5-alpha,6-alpha)-
• Morphinan-6-alpha-ol, 3-(benzyloxy)-7,8-didehydro-4,5-alpha-epoxy-17-methyl-
• (4R,4aR,7S,7aR,12bS)-3-methyl-9-phenylmethoxy-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
• Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-17-methyl-3-(phenylmethoxy)-, (5.alpha.,6.alpha.)-
• Morphinan-6.alpha.-ol, 3-(benzyloxy)-7,8-didehydro-4,5.alpha.-epxoy-17-methyl-
• (1S,5R,13R,14S,17R)-10-(benzyloxy)-4-methyl-12-oxa-4-azapentacyclo(9.6.1.01,13.0?,1?.0?,1?)octadeca-7(18),8,10,15-tetraen-14-ol
• (1S,5R,13R,14S,17R)-10-(benzyloxy)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.0?,1?.0?,1?]octadeca-7(18),8,10,15-tetraen-14-ol
• (4R,4aR,7S,7aR,12bS)-3-methyl-9-phenylmethoxy-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinolin-7-ol
• RefChem:118956
• 7,8-Didehydro-4,5-epoxy-17-methyl-3-(phenylmethoxy)morphinan-6-ol
• DTXCID4084737
• Morphinan-6-.alpha.-ol, 3-(benzyloxy)-7,8-didehydro-4,5-.alpha.-epoxy-17-methyl-
• Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-17-methyl-3-(phenylmethoxy)-, (5alpha,6alpha)-
• Morphinan-6alpha-ol, 3-(benzyloxy)-7,8-didehydro-4,5alpha-epxoy-17-methyl-
• 238-230-0
• Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-17-methyl-3-(phenylmethoxy)-, (5-alpha,6-alpha)-(9CI)
• 3-BENZYLMORPHINE
• RDJGWRFTDZZXSM-UHFFFAOYSA-N
• 3-O-Benzylmorphine
• DEA No. 9052
• benzylmorphin
• SCHEMBL24880
• SCHEMBL29359245
• RDJGWRFTDZZXSM-RNWLQCGYSA-N
• DB01573
• NS00024648
• Q4083783
• MORPHINAN-6-ALPHA-OL, 3-(BENZYLOXY)-7,8-DIDEHYDRO-4,5-ALPHA- EPOXY-17-METHYL-
• Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-17-methyl-3-(phenylmethoxy)-, (5a,6a)-; Morphinan-6a-ol, 3-(benzyloxy)-7,8-didehydro-4,5a-epoxy-17-methyl- (8CI); Benzylmorphine; O3-Benzylmorphine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9764	97.64%
Caco-2	+	0.5176	51.76%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.8429	84.29%
Subcellular localzation	Mitochondria	0.5504	55.04%
OATP2B1 inhibitior	-	0.8585	85.85%
OATP1B1 inhibitior	+	0.9129	91.29%
OATP1B3 inhibitior	+	0.9506	95.06%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.8785	87.85%
P-glycoprotein inhibitior	+	0.7918	79.18%
P-glycoprotein substrate	+	0.7535	75.35%
CYP3A4 substrate	+	0.7761	77.61%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.7047	70.47%
CYP3A4 inhibition	-	0.8889	88.89%
CYP2C9 inhibition	-	0.9054	90.54%
CYP2C19 inhibition	-	0.8224	82.24%
CYP2D6 inhibition	+	0.6622	66.22%
CYP1A2 inhibition	-	0.7559	75.59%
CYP2C8 inhibition	-	0.8802	88.02%
CYP inhibitory promiscuity	-	0.7001	70.01%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6460	64.60%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9799	97.99%
Skin irritation	-	0.7811	78.11%
Skin corrosion	-	0.9386	93.86%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7323	73.23%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.7159	71.59%
skin sensitisation	-	0.8319	83.19%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.8419	84.19%
Acute Oral Toxicity (c)	III	0.6789	67.89%
Estrogen receptor binding	+	0.5766	57.66%
Androgen receptor binding	-	0.6122	61.22%
Thyroid receptor binding	+	0.5454	54.54%
Glucocorticoid receptor binding	+	0.5919	59.19%
Aromatase binding	-	0.6376	63.76%
PPAR gamma	+	0.6375	63.75%
Honey bee toxicity	-	0.7331	73.31%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.8997	89.97%

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	99.62%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.55%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.74%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.50%	95.56%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	84.47%	85.83%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.44%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.44%	95.89%
CHEMBL1914	P06276	Butyrylcholinesterase	82.40%	95.00%
CHEMBL2581	P07339	Cathepsin D	81.47%	98.95%
CHEMBL4208	P20618	Proteasome component C5	81.42%	90.00%
CHEMBL3891	P07384	Calpain 1	81.09%	93.04%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.50%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.29%	85.14%
CHEMBL2319	P06870	Kallikrein 1	80.21%	90.95%

Plants that contains it

• Papaver somniferum

Cross-Links

• PubChem: 5362507
• NPASS: NPC44953
• LOTUS: LTS0102197
• wikiData: Q4083783