Norcodeine

Details

• Internal ID: a63dfc57-253f-4556-bacc-d2be2a273d77
• Taxonomy: Alkaloids and derivatives > Morphinans
• IUPAC Name: (4R,4aR,7S,7aR,12bS)-9-methoxy-1,2,3,4,4a,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
• SMILES (Canonical): COC1=C2C3=C(CC4C5C3(CCN4)C(O2)C(C=C5)O)C=C1
• SMILES (Isomeric): COC1=C2C3=C(C[C@@H]4[C@H]5[C@]3(CCN4)[C@@H](O2)[C@H](C=C5)O)C=C1
• InChI: InChI=1S/C17H19NO3/c1-20-13-5-2-9-8-11-10-3-4-12(19)16-17(10,6-7-18-11)14(9)15(13)21-16/h2-5,10-12,16,18-19H,6-8H2,1H3/t10-,11+,12-,16-,17-/m0/s1
• InChI Key: HKOIXWVRNLGFOR-KOFBORESSA-N
• Popularity: 242 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₉NO₃
• Molecular Weight: 285.34 g/mol
• Exact Mass: 285.13649347 g/mol
• Topological Polar Surface Area (TPSA): 50.70 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.16
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• N-Desmethylcodeine
• Norcodeina
• 467-15-2
• N-Demethylcodeine
• Norcodeinum
• (-)-N-Norcodeine
• Normorphine 3-methyl ether
• 3-o-methylnormorphine
• 32W9P3T4ML
• DTXSID8046327
• IDS-NN-005(SECT.2)
• DTXCID6026327
• CHEBI:80579
• (4R,4aR,7S,7aR,12bS)-9-methoxy-1,2,3,4,4a,7,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
• (4R,4aR,7S,7aR,12bS)-9-methoxy-1,2,3,4,4a,7,7a,13-octahydro-4,12-methanobenzofuro(3,2-e)isoquinolin-7-ol
• RefChem:166579
• (4R,12bS)-9-methoxy-1,2,3,4,4a,7,7a,13-octahydro-4,12-methanobenzofuro(3,2-e)isoquinoline-7-ol
• (4R,4aR,7S,7aR,12bS)-9-methoxy-1,2,3,4,4a,7,7a,13-octahydro-4,12-methanobenzofuro(3,2-e)isoquinoline-7-ol
• 207-388-2
• (-)-Norcodeine
• Norcodeine [INN:BAN]
• Norcodeinum [INN-Latin]
• Norcodeina [INN-Spanish]
• UNII-32W9P3T4ML
• NCGC00163182-01
• EINECS 207-388-2
• NORCODEINE [MI]
• NORCODEINE [INN]
• SCHEMBL120270
• Norcodeine, 1mg/ml in Methanol
• CHEMBL1908321
• SCHEMBL29776979
• HKOIXWVRNLGFOR-KOFBORESSA-N
• 7,8-Didehydro-4,5-alpha-epoxy-3-methoxymorphinan-6-alpha-ol
• BDBM224030
• Norcodeine 1.0 mg/ml in Methanol
• Norcodeine (stereochemistry defined)
• Tox21_112027
• NCGC00186625-01
• AS-17006
• CAS-467-15-2
• NS00009228
• CODEINE MONOHYDRATE IMPURITY H [EP IMPURITY]
• Q4327388
• 3-methoxy-7,8-didehydro-4,5alpha-epoxymorphinan-6alpha-ol
• CODEINE HYDROCHLORIDE DIHYDRATE IMPURITY H [EP IMPURITY]
• CODEINE PHOSPHATE HEMIHYDRATE IMPURITY H [EP IMPURITY]
• Morphinan-6-alpha-ol, 7,8-didehydro-4,5-alpha-epoxy-3-methoxy-
• Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-, (5-alpha,6-alpha)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9943	99.43%
Caco-2	+	0.6917	69.17%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6252	62.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9258	92.58%
OATP1B3 inhibitior	+	0.9565	95.65%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.7914	79.14%
P-glycoprotein inhibitior	-	0.8947	89.47%
P-glycoprotein substrate	+	0.5372	53.72%
CYP3A4 substrate	+	0.5817	58.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.6390	63.90%
CYP3A4 inhibition	-	0.8234	82.34%
CYP2C9 inhibition	-	0.8586	85.86%
CYP2C19 inhibition	-	0.7452	74.52%
CYP2D6 inhibition	+	0.5881	58.81%
CYP1A2 inhibition	-	0.7611	76.11%
CYP2C8 inhibition	-	0.8314	83.14%
CYP inhibitory promiscuity	-	0.5501	55.01%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5685	56.85%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9949	99.49%
Skin irritation	-	0.7194	71.94%
Skin corrosion	-	0.9207	92.07%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6889	68.89%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.6284	62.84%
skin sensitisation	-	0.6074	60.74%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.5518	55.18%
Acute Oral Toxicity (c)	II	0.5114	51.14%
Estrogen receptor binding	-	0.7925	79.25%
Androgen receptor binding	-	0.7219	72.19%
Thyroid receptor binding	+	0.5802	58.02%
Glucocorticoid receptor binding	-	0.6207	62.07%
Aromatase binding	-	0.8299	82.99%
PPAR gamma	-	0.6197	61.97%
Honey bee toxicity	-	0.7296	72.96%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	-	0.6672	66.72%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293224	P10636	Microtubule-associated protein tau	79.4 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.69%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.57%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.66%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.42%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.48%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.22%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.32%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.56%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.93%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.90%	97.14%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	81.87%	96.39%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	81.00%	89.05%
CHEMBL2535	P11166	Glucose transporter	80.78%	98.75%

Plants that contains it

• Papaver somniferum

Cross-Links

• PubChem: 9925873
• NPASS: NPC157958