(1R,9R,10S)-3,6-dihydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraene-8,13-dione

Details

• Internal ID: d2116c35-e599-4a18-b1bb-7cc6a49d940d
• Taxonomy: Alkaloids and derivatives > Morphinans
• IUPAC Name: (1R,9R,10S)-3,6-dihydroxy-4,12-dimethoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,11-tetraene-8,13-dione
• SMILES (Canonical): CN1CCC23CC(=O)C(=CC2C1C(=O)C4=C3C(=C(C=C4O)OC)O)OC
• SMILES (Isomeric): CN1CC[C@@]23CC(=O)C(=C[C@@H]2[C@@H]1C(=O)C4=C3C(=C(C=C4O)OC)O)OC
• InChI: InChI=1S/C19H21NO6/c1-20-5-4-19-8-11(22)12(25-2)6-9(19)16(20)18(24)14-10(21)7-13(26-3)17(23)15(14)19/h6-7,9,16,21,23H,4-5,8H2,1-3H3/t9-,16-,19-/m1/s1
• InChI Key: MUBFHGMAWFRQOZ-JCICBKHFSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₁NO₆
• Molecular Weight: 359.40 g/mol
• Exact Mass: 359.13688739 g/mol
• Topological Polar Surface Area (TPSA): 96.30 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.36
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8083	80.83%
Caco-2	+	0.7054	70.54%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.5579	55.79%
OATP2B1 inhibitior	-	0.8587	85.87%
OATP1B1 inhibitior	+	0.9086	90.86%
OATP1B3 inhibitior	+	0.9359	93.59%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7000	70.00%
BSEP inhibitior	-	0.5674	56.74%
P-glycoprotein inhibitior	-	0.8152	81.52%
P-glycoprotein substrate	-	0.5163	51.63%
CYP3A4 substrate	+	0.6556	65.56%
CYP2C9 substrate	-	0.8247	82.47%
CYP2D6 substrate	-	0.6961	69.61%
CYP3A4 inhibition	-	0.8855	88.55%
CYP2C9 inhibition	-	0.9012	90.12%
CYP2C19 inhibition	-	0.8943	89.43%
CYP2D6 inhibition	-	0.6843	68.43%
CYP1A2 inhibition	-	0.5597	55.97%
CYP2C8 inhibition	-	0.8261	82.61%
CYP inhibitory promiscuity	-	0.9426	94.26%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5811	58.11%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.8978	89.78%
Skin irritation	-	0.7618	76.18%
Skin corrosion	-	0.9353	93.53%
Ames mutagenesis	-	0.7354	73.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.8134	81.34%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	-	0.6211	62.11%
skin sensitisation	-	0.8628	86.28%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.7838	78.38%
Acute Oral Toxicity (c)	III	0.6265	62.65%
Estrogen receptor binding	-	0.6320	63.20%
Androgen receptor binding	+	0.5757	57.57%
Thyroid receptor binding	-	0.5806	58.06%
Glucocorticoid receptor binding	+	0.7684	76.84%
Aromatase binding	-	0.6392	63.92%
PPAR gamma	-	0.5872	58.72%
Honey bee toxicity	-	0.8307	83.07%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.8542	85.42%

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	98.52%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.50%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.37%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.36%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.06%	94.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	91.73%	91.03%
CHEMBL4208	P20618	Proteasome component C5	91.54%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.43%	95.89%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	90.81%	93.40%
CHEMBL2581	P07339	Cathepsin D	90.56%	98.95%
CHEMBL2535	P11166	Glucose transporter	89.30%	98.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.19%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.07%	90.71%
CHEMBL1937	Q92769	Histone deacetylase 2	87.23%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.22%	94.45%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.94%	93.03%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.23%	92.94%
CHEMBL2056	P21728	Dopamine D1 receptor	85.11%	91.00%
CHEMBL5203	P33316	dUTP pyrophosphatase	84.46%	99.18%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	83.88%	100.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.26%	93.99%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	81.80%	94.42%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.57%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.18%	93.04%
CHEMBL261	P00915	Carbonic anhydrase I	80.13%	96.76%

Plants that contains it

• Sinomenium acutum

Cross-Links

• PubChem: 53348539
• LOTUS: LTS0014425
• wikiData: Q105172038