Thebacon

Details

• Internal ID: 55eb69a5-95d3-45eb-bd8e-387a298fd08f
• Taxonomy: Alkaloids and derivatives > Morphinans
• IUPAC Name: [(4R,4aR,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] acetate
• InChI: InChI=1S/C20H23NO4/c1-11(22)24-16-7-5-13-14-10-12-4-6-15(23-3)18-17(12)20(13,19(16)25-18)8-9-21(14)2/h4,6-7,13-14,19H,5,8-10H2,1-3H3/t13-,14+,19-,20-/m0/s1
• InChI Key: RRJQTGHQFYTZOW-ILWKUFEGSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₃NO₄
• Molecular Weight: 341.40 g/mol
• Exact Mass: 341.16270821 g/mol
• Topological Polar Surface Area (TPSA): 48.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.42
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 2

Synonyms

• Tebacon
• Thebacone
• Acetyldihydrocodeinone
• Acedikon
• Tebacona
• Tebacone
• Thebaconum
• Acedikon [Czech]
• Tebacone [DCIT]
• Acetyldihydrokodeinon
• Acetyldemethyldihydrothebaine
• Dihydrocodeinone enol acetate
• DEA No. 9315
• Tebacona [INN-Spanish]
• Thebacone [INN-French]
• Thebaconum [INN-Latin]
• Thebacon [INN:BAN:DCF]
• Acedicon
• Thebacon (INN)
• Acetyldihydrokodeinon [Czech]
• UNII-520D430GDK
• IDS-NT-001
• 466-90-0
• 520D430GDK
• THEBACON [INN]
• THEBACON [MI]
• Thebaine, demethyldihydro-, acetate
• EINECS 207-377-2
• THEBACON [WHO-DD]
• NSC 117860
• NSC-117860
• BRN 0056871
• DTXSID90891944
• 4-27-00-02218 (Beilstein Handbook Reference)
• Demethyldihydrothebaine, acetate
• Acetyldihydrochodeinone
• Tebacona (INN-Spanish)
• Thebacone (INN-French)
• Thebaconum (INN-Latin)
• Demethyldihydrothebaine acetate (ester)
• MORPHINAN-6-OL, 6,7-DIDEHYDRO-4,5-alpha-EPOXY-3-METHOXY-17-METHYL-, ACETATE
• Morphinan-6-ol, 6,7-didehydro-4,5-epoxy-3-methoxy-17-methyl-, 6-acetate, (5.alpha.)-
• Morphinan-6-ol, 6,7-didehydro-4,5-epoxy-3-methoxy-17-methyl-, acetate (ester), (5alpha)-
• Morphinan-6-ol, 6,7-didehydro-4,5alpha-epoxy-3-methoxy-17-methyl-, acetate (ester)
• ((4R,4aR,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinolin-7-yl) acetate
• (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-7,9,11(18),14-tetraen-14-yl acetate
• (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-7,9,11(18),14-tetraen-14-yl acetate
• [(4R,4aR,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl] acetate
• 10-Methoxy-4-methyl-12-oxa-4-azapentacyclo(9.6.1.0,.0,.0,)octadeca-7(18),8,10,14-tetraen-14-yl acetic acid
• 10-Methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0,.0,.0,]octadeca-7(18),8,10,14-tetraen-14-yl acetic acid
• Thebaine, demethyldihydro-, acetate (ester)
• RefChem:189142
• 3-Methoxy-N-methyl-4,5-epoxymorphin-6-en-6-yl acetate
• Morphinan-6-ol, 6,7-didehydro-4,5-epoxy-3-methoxy-17-methyl-, acetate, (5.alpha.)-
• Morphinan-6-ol, 6,7-didehydro-4,5.alpha.-epoxy-3-methoxy-17-methyl-, acetate (ester)
• Morphinan-6-ol, 6,7-didehydro-4,5.alpha.-epoxy-3-methoxy-17-methyl-,acetate
• DTXCID601031456
• Morphinan-6-ol, 6,7-didehydro-4,5-epoxy-3-methoxy-17-methyl-, acetate (ester), (5.alpha.)-
• Morphinan-6-ol, 6,7-didehydro-4,5alpha-epoxy-3-methoxy-17-methyl-,acetate
• Morphinan-6-ol, 6,7-didehydro-4,5-epoxy-3-methoxy-17-methyl-, acetate, (5alpha)-
• Morphinan-6-ol, 6,7-didehydro-4,5alpha-epoxy-3-methoxy-17-methyl-, acetate (ester) (8CI)
• 207-377-2
• MORPHINAN-6-OL, 6,7-DIDEHYDRO-4,5-EPOXY-3-METHOXY-17-METHYL-, 6-ACETATE, (5ALPHA)-
• Morphinan-6-ol, 6,7-didehydro-4,5-epoxy-3-methoxy-17-methyl-, acetate (ester), (5alpha)-(9CI)
• (9-methoxy-3-methyl-2,4,4a,5,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinolin-7-yl) acetate
• (9-methoxy-3-methyl-2,4,4a,5,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-yl) acetate
• RRJQTGHQFYTZOW-UHFFFAOYSA-N
• Thebacetyl
• SCHEMBL25766
• CHEMBL2104751
• SCHEMBL29632752
• CHEBI:135449
• RRJQTGHQFYTZOW-ILWKUFEGSA-N
• DB13458
• D07386
• Q2787672
• Thebacon; Morphinan-6-ol, 6,7-didehydro-4,5-epoxy-3-methoxy-17-methyl-, 6-acetate, (5a)-; Morphinan-6-ol, 6,7-didehydro-4,5-epoxy-3-methoxy-17-methyl-, acetate (ester), (5a)- (9CI); Morphinan-6-ol, 6,7-didehydro-4,5a-epoxy-3-methoxy-17-methyl-, acetate (ester) (8CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9721	97.21%
Caco-2	+	0.8260	82.60%
Blood Brain Barrier	+	1.0000	100.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.4104	41.04%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9081	90.81%
OATP1B3 inhibitior	+	0.9354	93.54%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.6500	65.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	-	0.5412	54.12%
P-glycoprotein substrate	+	0.7138	71.38%
CYP3A4 substrate	+	0.7281	72.81%
CYP2C9 substrate	-	0.7954	79.54%
CYP2D6 substrate	+	0.4156	41.56%
CYP3A4 inhibition	-	0.7301	73.01%
CYP2C9 inhibition	-	0.8903	89.03%
CYP2C19 inhibition	-	0.8443	84.43%
CYP2D6 inhibition	+	0.6162	61.62%
CYP1A2 inhibition	-	0.7900	79.00%
CYP2C8 inhibition	-	0.9281	92.81%
CYP inhibitory promiscuity	-	0.7398	73.98%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5982	59.82%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9911	99.11%
Skin irritation	-	0.7940	79.40%
Skin corrosion	-	0.9400	94.00%
Ames mutagenesis	-	0.7154	71.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7376	73.76%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.8374	83.74%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.7375	73.75%
Acute Oral Toxicity (c)	III	0.5715	57.15%
Estrogen receptor binding	+	0.5401	54.01%
Androgen receptor binding	-	0.6719	67.19%
Thyroid receptor binding	-	0.5103	51.03%
Glucocorticoid receptor binding	+	0.5681	56.81%
Aromatase binding	-	0.7028	70.28%
PPAR gamma	-	0.5201	52.01%
Honey bee toxicity	-	0.6453	64.53%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9757	97.57%

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	99.66%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.29%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.12%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.36%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.37%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.34%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.57%	94.00%
CHEMBL217	P14416	Dopamine D2 receptor	85.68%	95.62%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	85.35%	90.95%
CHEMBL340	P08684	Cytochrome P450 3A4	84.32%	91.19%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	84.07%	89.05%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.01%	89.50%

Plants that contains it

• Papaver somniferum

Cross-Links

• PubChem: 11508377
• NPASS: NPC70075