Nalorphine

Details

• Internal ID: b3ca8761-af39-4d7d-b5ba-7bb752ad335f
• Taxonomy: Alkaloids and derivatives > Morphinans
• IUPAC Name: (4R,4aR,7S,7aR,12bS)-3-prop-2-enyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
• InChI: InChI=1S/C19H21NO3/c1-2-8-20-9-7-19-12-4-6-15(22)18(19)23-17-14(21)5-3-11(16(17)19)10-13(12)20/h2-6,12-13,15,18,21-22H,1,7-10H2/t12-,13+,15-,18-,19-/m0/s1
• InChI Key: UIQMVEYFGZJHCZ-SSTWWWIQSA-N
• Popularity: 2,387 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₁NO₃
• Molecular Weight: 311.40 g/mol
• Exact Mass: 311.15214353 g/mol
• Topological Polar Surface Area (TPSA): 52.90 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.75
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• Nalorfina
• N-Allylnormorphine
• 62-67-9
• Nalorphinum
• Allylnormorphine
• Nalorphine serb
• Normorphine, N-allyl-
• N-Allyl-N-desmethylmorphine
• U59WB2WRY2
• NANM
• N-Allyl-7,8-dehydro-4,5-epoxy-3,6-dihydroxymorphinan
• DTXSID3023348
• Morphinan-3,6-alpha-diol, 17-allyl-7,8-didehydro-4,5-alpha-epoxy-
• Morphinan-3,6-diol, 7,8-didehydro-4,5-epoxy-17-(2-propenyl)-, (5alpha,6alpha)-
• (-)-Nalorphine
• (1S,5R,13R,14S,17R)-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo(9.6.1.0^(1,13).0^(5,17).0^(7,18))octadeca-7(18),8,10,15-tetraene-10,14-diol
• (1S,5R,13R,14S,17R)-4-(prop-2-en-1-yl)-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraene-10,14-diol
• (4R,4aR,7S,7aR,12bS)-3-allyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinoline-7,9-diol
• (4R,4aR,7S,7aR,12bS)-3-allyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
• (4R,4aR,7S,7aR,12bS)-3-prop-2-enyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinoline-7,9-diol
• (4R,4aR,7S,7aR,12bS)-3-prop-2-enyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol
• Hydrobromide, Nalorphine
• Hydrochloride, Nalorphine
• RefChem:164455
• DTXCID303348
• V03AB02
• 200-546-1
• Allorphine
• Nalorphinium
• Anthorphine
• Antorfin
• Antorphin
• Antorphine
• Nalorphin
• Anarcon
• Nallin
• Norfin
• Acetorfin
• CHEBI:7458
• Nalorphine (INN)
• DEA No. 9400
• NALORPHINE [INN]
• Acetorfin [Czech]
• Nalorfina [DCIT]
• Nalorphine [INN:BAN]
• Nalorphinum [INN-Latin]
• HSDB 3278
• NCGC00168255-01
• EINECS 200-546-1
• UNII-U59WB2WRY2
• N-allyl-normorphine
• Nalorphine serb (TN)
• NALORPHINE [MI]
• 7,8-Didehydro-4,5-epoxy-17-(2-propenyl)morphinan-3,6-diol
• NALORPHINE [HSDB]
• NALORPHINE [MART.]
• NALORPHINE [WHO-DD]
• SCHEMBL38920
• CHEMBL415284
• GTPL1629
• BDBM50367061
• PDSP2_001572
• DB11490
• NS00008614
• D08247
• Q2622916
• (5alpha,6alpha)-17-prop-2-en-1-yl-7,8-didehydro-4,5-epoxymorphinan-3,6-diol
• MORPHINAN-3,6-DIOL, 7,8-DIDEHYDRO-4,5-EPOXY-17-(2-PROPENYL)-(5.ALPHA.,6.ALPHA.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9561	95.61%
Caco-2	+	0.6452	64.52%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6734	67.34%
OATP2B1 inhibitior	-	0.8615	86.15%
OATP1B1 inhibitior	+	0.9293	92.93%
OATP1B3 inhibitior	+	0.9486	94.86%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.8742	87.42%
P-glycoprotein inhibitior	-	0.8290	82.90%
P-glycoprotein substrate	+	0.7948	79.48%
CYP3A4 substrate	+	0.6866	68.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.6725	67.25%
CYP3A4 inhibition	-	0.8521	85.21%
CYP2C9 inhibition	-	0.9068	90.68%
CYP2C19 inhibition	-	0.8442	84.42%
CYP2D6 inhibition	-	0.6001	60.01%
CYP1A2 inhibition	-	0.5841	58.41%
CYP2C8 inhibition	-	0.8838	88.38%
CYP inhibitory promiscuity	-	0.6184	61.84%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5835	58.35%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9779	97.79%
Skin irritation	-	0.7492	74.92%
Skin corrosion	-	0.9126	91.26%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6528	65.28%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.7625	76.25%
skin sensitisation	-	0.7556	75.56%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8371	83.71%
Acute Oral Toxicity (c)	III	0.5530	55.30%
Estrogen receptor binding	-	0.6700	67.00%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	+	0.6238	62.38%
Glucocorticoid receptor binding	+	0.5758	57.58%
Aromatase binding	-	0.6702	67.02%
PPAR gamma	+	0.6551	65.51%
Honey bee toxicity	-	0.7234	72.34%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.8096	80.96%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL236	P41143	Delta opioid receptor	120 nM; 120 nM	Ki; Ki	via Super-PRED; PMID: 19027293
CHEMBL237	P41145	Kappa opioid receptor	2 nM; 0.38 nM; 0.38 nM	Ki; Ki; Ki	PMID: 26390077; via Super-PRED; PMID: 19027293
CHEMBL233	P35372	Mu opioid receptor	0.36 nM; 0.19 nM; 0.19 nM	Ki; Ki; Ki	PMID: 26390077; via Super-PRED; PMID: 19027293
CHEMBL287	Q99720	Sigma opioid receptor	735 nM; 1800 nM; 2850 nM; 4000 nM; 48 nM; 93 nM; 625 nM	IC50; IC50; IC50; IC50; IC50; IC50; IC50	PMID: 1469697; PMID: 1469697; PMID: 1469697; PMID: 1469697; PMID: 1469697; PMID: 1469697; PMID: 1469697

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.04%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.95%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	94.83%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.21%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.73%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.61%	95.56%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.02%	90.24%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.90%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.29%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.13%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.07%	100.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.25%	91.03%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	81.91%	89.62%
CHEMBL238	Q01959	Dopamine transporter	81.14%	95.88%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	80.57%	98.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.29%	93.04%

Plants that contains it

• Papaver somniferum

Cross-Links

• PubChem: 5284595
• NPASS: NPC243483
• ChEMBL: CHEMBL415284
• LOTUS: LTS0175846
• wikiData: Q2622916