Hydrocodone

Details

• Internal ID: 8dcb0a19-27f2-43fd-9e46-f147a90833b9
• Taxonomy: Alkaloids and derivatives > Morphinans
• IUPAC Name: (4R,4aR,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• InChI: InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-12,17H,4-5,7-9H2,1-2H3/t11-,12+,17-,18-/m0/s1
• InChI Key: LLPOLZWFYMWNKH-CMKMFDCUSA-N
• Popularity: 4,088 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₁NO₃
• Molecular Weight: 299.40 g/mol
• Exact Mass: 299.15214353 g/mol
• Topological Polar Surface Area (TPSA): 38.80 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.93
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

• Dihydrocodeinone
• Hydrocodon
• Hydrocone
• Hydroconum
• Multacodin
• Bekadid
• hidrocodona
• Idrocodone
• (-)-Dihydrocodeinone
• 125-29-1
• DICO
• Hydrocodonum
• 4,5-alpha-Epoxy-3-methoxy-17-methylmorphinan-6-one
• 6-Oxo-3-methoxy-N-methyl-4,5-epoxymorphinan
• 6YKS4Y3WQ7
• CHEBI:5779
• NSC-19044
• DTXSID8023131
• Morphinan-6-one, 4,5alpha-epoxy-3-methoxy-17-methyl-
• Morphinan-6-one, 4,5-alpha-epoxy-3-methoxy-17-methyl-
• Morphinan-6-one, 4,5-epoxy-3-methoxy-17-methyl-, (5alpha)-
• (4R,4aR,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one
• Hydrocodeinonebitartrate
• (1S,5R,13R,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo(9.6.1.0^(1,13).0^(5,17).0^(7,18))octadeca-7(18),8,10-trien-14-one
• (1S,5R,13R,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-one
• (4R,4aR,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro(3,2-e)isoquinolin-7-one
• (4R,4aR,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro(3,2-e)isoquinoline-7-one
• (4R,4aR,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one
• RefChem:5891
• DTXCID803131
• R05DA03
• Hydrocodone Tartrate (1:1), Hydrate (2:5)
• (1S,5R,13R,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo(9.6.1.01,13.05,17.07,18)octadeca-7(18),8,10-trien-14-one
• 204-733-9
• Codinovo
• Idrocodone [DCIT]
• Hydrocodonum [INN-Latin]
• Hidrocodona [INN-Spanish]
• Dicodid
• Codeinone, dihydro-
• Hydrocodone (INN)
• 4,5alpha-Epoxy-3-methoxy-17-methylmorphinan-6-one
• HYDROCODONE [INN]
• NSC 19044
• Hydrocodone [INN:BAN]
• Hydrocodone polistirex
• HSDB 3097
• NCGC00159317-02
• EINECS 204-733-9
• 4,5.alpha.-Epoxy-3-methoxy-17-methylmorphinan-6-one
• UNII-6YKS4Y3WQ7
• BRN 0094193
• opioid1
• DEA No. 9193
• HYDROCODONE-
• HYDROCODONE [MI]
• HYDROCODONE [HSDB]
• HYDROCODONE [VANDF]
• SCHEMBL2987
• CHEMBL1457
• HYDROCODONE [WHO-DD]
• 4-27-00-03580 (Beilstein Handbook Reference)
• 3-methoxy-17-methyl-4,5alpha-epoxymorphinan-6-one
• Hydrocodone polistirex [USAN]
• Morphinan-6-one, 4,5-epoxy-3-methoxy-17-methyl-, (5.alpha.)-
• GTPL7081
• SCHEMBL29392417
• Hydrocodone, 1mg/ml in Methanol
• HYDROCODONE CII [USP-RS]
• (5alpha)-17-methyl-3-(methyloxy)-4,5-epoxymorphinan-6-one
• Hydrocodone 0.1 mg/ml in Methanol
• Hydrocodone 1.0 mg/ml in Methanol
• BDBM50386689
• Hydrocodone (1.0mg/mL in Methanol)
• DB00956
• NCGC00159317-03
• DB-243593
• NS00009201
• C08024
• D08045
• Q411441
• 17-methyl-4,5alpha-epoxy-3-methoxymorphinan-6-one
• 4,5alpha-epoxy-3-methoxy-17-methyl-morphinan-6-one
• Morphinan-6-one,5.alpha.-epoxy-3-methoxy-17-methyl-
• OXYCODONE HYDROCHLORIDE IMPURITY E [EP IMPURITY]
• OXYCODONE HYDROCHLORIDE, HYDROCODONE- [USP IMPURITY]
• Morphinan-6-one,5-epoxy-3-methoxy-17-methyl-, (5.alpha.)-
• (5.ALPHA.)-3-METHOXY-17-METHYL-4,5-EPOXYMORPHINAN-6-ONE
• DIHYDROCODEINE HYDROGEN TARTRATE IMPURITY C [EP IMPURITY]
• WLN: T B6566 B6/CO 4ABBC R BX FV HO PN GHT&&TTJ JO1 P1
• 4aH-8,5-bcd]furan-5-(6H)-one, 7,7a,8,9-tetrahydro-3-methoxy-12-methyl-
• 50678-79-0

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9904	99.04%
Caco-2	+	0.8977	89.77%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Lysosomes	0.4837	48.37%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.9241	92.41%
OATP1B3 inhibitior	+	0.9505	95.05%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.7028	70.28%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	+	0.8175	81.75%
CYP3A4 substrate	+	0.7328	73.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.7047	70.47%
CYP3A4 inhibition	-	0.7625	76.25%
CYP2C9 inhibition	-	0.9412	94.12%
CYP2C19 inhibition	-	0.8402	84.02%
CYP2D6 inhibition	+	0.6629	66.29%
CYP1A2 inhibition	-	0.8207	82.07%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.8675	86.75%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6651	66.51%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9827	98.27%
Skin irritation	-	0.8307	83.07%
Skin corrosion	-	0.9438	94.38%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6483	64.83%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.9250	92.50%
skin sensitisation	-	0.8395	83.95%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8530	85.30%
Acute Oral Toxicity (c)	II	0.5090	50.90%
Estrogen receptor binding	-	0.8071	80.71%
Androgen receptor binding	-	0.8512	85.12%
Thyroid receptor binding	-	0.6643	66.43%
Glucocorticoid receptor binding	+	0.6335	63.35%
Aromatase binding	-	0.7422	74.22%
PPAR gamma	-	0.4863	48.63%
Honey bee toxicity	-	0.7362	73.62%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.7529	75.29%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL237	P41145	Kappa opioid receptor	260 nM; 260 nM	Ki; Ki	PMID: 22439881; via Super-PRED
CHEMBL233	P35372	Mu opioid receptor	9.5 nM; 9.5 nM	Ki; Ki	PMID: 22439881; via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	8912.5 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.06%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.88%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	94.55%	95.89%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.87%	93.40%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.17%	97.25%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.69%	94.00%
CHEMBL217	P14416	Dopamine D2 receptor	89.34%	95.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.22%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.81%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.56%	86.33%
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	85.46%	96.86%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.55%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.76%	97.14%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.66%	93.99%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	83.37%	98.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.97%	90.71%
CHEMBL1902	P62942	FK506-binding protein 1A	80.87%	97.05%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	80.66%	90.95%

Plants that contains it

• Croton cortesianus
• Papaver somniferum

Cross-Links

• PubChem: 5284569
• NPASS: NPC115906
• ChEMBL: CHEMBL1457
• LOTUS: LTS0051765
• wikiData: Q104987777