Dihydrocodeine

Details

• Internal ID: 25ccc82e-89f1-4b88-8a6e-0af16703927f
• Taxonomy: Alkaloids and derivatives > Morphinans
• IUPAC Name: (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
• SMILES (Canonical): CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(CC4)O
• SMILES (Isomeric): CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](CC4)O
• InChI: InChI=1S/C18H23NO3/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/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
• InChI Key: RBOXVHNMENFORY-DNJOTXNNSA-N
• Popularity: 2,016 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₃NO₃
• Molecular Weight: 301.40 g/mol
• Exact Mass: 301.16779360 g/mol
• Topological Polar Surface Area (TPSA): 41.90 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.73
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• Codhydrine
• Dehacodin
• Novicondin
• Rapacodin
• Dihydroneopine
• Hydrocodeine
• Hydrocodin
• 8,14-Dihydroneopine
• 125-28-0
• Cohydrin
• (-)-Dihydrocodeine
• Didrate
• Dihydrin
• Nadeine
• Novicodin
• Paracodine
• Parzone
• alpha-Hydrocodol
• 6alpha-Hydrocodol
• 6-alpha-Hydrocodol
• 7,8-Dihydrocodeine
• Paracodin
• Drocode
• Dihydrocodeine [INN]
• Dihydrokodein [Czech]
• Diidrocodeina [DCIT]
• Dihidrocodeina
• Dihydrocodeinum
• Dihydrokodein
• Diidrocodeina
• Remedacen
• Codeine, 7,8-dihydro-
• DH-codeine
• Dihydrocodeine [INN:BAN]
• .alpha.-Hydrocodol
• Dihydrocodeinum [INN-Latin]
• Dihidrocodeina [INN-Spanish]
• EINECS 204-732-3
• NSC 231319
• UNII-N9I9HDB855
• N9I9HDB855
• DEA No. 9120
• parzone bitartrate
• IDS-ND-008(SECT.2)
• 6-Hydroxy-3-methoxy-N-methyl-4,5-epoxymorphinan
• 3-Methoxy-12-methyl-5,6,7,7a,8,9-hexahydro-4aH-8,9c-iminoethanophenanthro(4,5-bcd)furan-5-ol
• NSC-231319
• Dihydrocodeine (INN)
• Morphinan-6alpha-ol, 4,5alpha-epoxy-3-methoxy-17-methyl-
• Morphinan-6-alpha-ol, 4,5-alpha-epoxy-3-methoxy-17-methyl-
• Morphinan-6-ol, 4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)-
• paramol 118
• dihydrocodein
• Paracodeine
• Dicogesic
• Remedacen (TN)
• Dihydrocodeine (oral)
• D0T6RC
• DIHYDROCODEINE [MI]
• CHEMBL1595
• SCHEMBL24607
• 4,5.alpha.-Epoxy-3-methoxy-17-methylmorphinan-6.alpha.-ol
• DIHYDROCODEINE [VANDF]
• DIHYDROCODEINE [MART.]
• GTPL7594
• DIHYDROCODEINE [WHO-DD]
• Dihydrocodeine (oral), Shionogi
• DTXSID5022936
• CHEBI:135276
• RBOXVHNMENFORY-DNJOTXNNSA-N
• (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
• DB01551
• LS-91966
• OC1CCC2C3Cc4ccc(OC)c5OC1C2(CCN3C)c45
• D07831
• S-8115
• Q377270
• MORPHINAN-6-OL, 4,5-EPOXY-3-METHOXY-17-METHYL-
• Morphinan-6-ol, 4,5-epoxy-3-methoxy-17-methyl-, (5?,6?)-
• (5-alpha,6-alpha)-4,5-Epoxy-3-methoxy-17-methylmorphinan-6-ol
• (5alpha,6alpha)-17-methyl-3-(methyloxy)-4,5-epoxymorphinan-6-ol
• Morfinan-6-ol, 4,5-epoxi-3-metoxi-17-metil-, (5alfa, 6alfa)-
• HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE IMPURITY B [EP IMPURITY]
• (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
• (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9890	98.90%
Caco-2	+	0.9354	93.54%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Lysosomes	0.6301	63.01%
OATP2B1 inhibitior	-	0.8607	86.07%
OATP1B1 inhibitior	+	0.9266	92.66%
OATP1B3 inhibitior	+	0.9355	93.55%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.8365	83.65%
P-glycoprotein inhibitior	-	0.9324	93.24%
P-glycoprotein substrate	+	0.7891	78.91%
CYP3A4 substrate	+	0.7979	79.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.7901	79.01%
CYP3A4 inhibition	-	0.8114	81.14%
CYP2C9 inhibition	-	0.9074	90.74%
CYP2C19 inhibition	-	0.7689	76.89%
CYP2D6 inhibition	+	0.7395	73.95%
CYP1A2 inhibition	-	0.8554	85.54%
CYP2C8 inhibition	-	0.9490	94.90%
CYP inhibitory promiscuity	-	0.9570	95.70%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6907	69.07%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9914	99.14%
Skin irritation	-	0.8023	80.23%
Skin corrosion	-	0.9380	93.80%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4681	46.81%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.8421	84.21%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.8448	84.48%
Acute Oral Toxicity (c)	II	0.7196	71.96%
Estrogen receptor binding	-	0.8683	86.83%
Androgen receptor binding	-	0.7350	73.50%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5540	55.40%
Aromatase binding	-	0.8289	82.89%
PPAR gamma	-	0.6083	60.83%
Honey bee toxicity	-	0.8418	84.18%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	-	0.4142	41.42%

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	95.10%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.35%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.22%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.51%	92.94%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.34%	89.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.27%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.26%	94.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	85.51%	91.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.32%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.40%	100.00%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	83.14%	98.00%
CHEMBL5203	P33316	dUTP pyrophosphatase	82.95%	99.18%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.91%	95.89%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	82.40%	95.78%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	81.89%	85.83%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.90%	100.00%

Plants that contains it

• Aloe microstigma
• Chrozophora plicata
• Papaver somniferum

Cross-Links

• PubChem: 5284543
• NPASS: NPC67346
• LOTUS: LTS0136293
• wikiData: Q377270