1-[(22S)-4-methoxy-2,12-diazahexacyclo[14.3.2.19,12.01,9.03,8.016,22]docosa-3(8),4,6-trien-2-yl]ethanone

Details

• Internal ID: f3517c1a-21fe-476b-839d-35c34d8bfa1c
• Taxonomy: Alkaloids and derivatives > Aspidospermatan-type alkaloids
• IUPAC Name: 1-[(22S)-4-methoxy-2,12-diazahexacyclo[14.3.2.19,12.01,9.03,8.016,22]docosa-3(8),4,6-trien-2-yl]ethanone
• SMILES (Canonical): CC(=O)N1C2=C(C=CC=C2OC)C34C15CCCC6(C3N(CCC6)CC4)CC5
• SMILES (Isomeric): CC(=O)N1C2=C(C=CC=C2OC)C34C15CCCC6([C@@H]3N(CCC6)CC4)CC5
• InChI: InChI=1S/C23H30N2O2/c1-16(26)25-19-17(6-3-7-18(19)27-2)23-13-15-24-14-5-9-21(20(23)24)8-4-10-22(23,25)12-11-21/h3,6-7,20H,4-5,8-15H2,1-2H3/t20-,21?,22?,23?/m0/s1
• InChI Key: QUJGDBXRYRHXEW-LEISRSHCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₀N₂O₂
• Molecular Weight: 366.50 g/mol
• Exact Mass: 366.230728204 g/mol
• Topological Polar Surface Area (TPSA): 32.80 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.87
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9740	97.40%
Caco-2	+	0.7361	73.61%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7113	71.13%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9379	93.79%
OATP1B3 inhibitior	+	0.9497	94.97%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	+	0.7250	72.50%
BSEP inhibitior	+	0.7795	77.95%
P-glycoprotein inhibitior	-	0.6361	63.61%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6641	66.41%
CYP2C9 substrate	-	0.8176	81.76%
CYP2D6 substrate	+	0.4404	44.04%
CYP3A4 inhibition	+	0.8882	88.82%
CYP2C9 inhibition	-	0.8547	85.47%
CYP2C19 inhibition	-	0.6672	66.72%
CYP2D6 inhibition	-	0.5447	54.47%
CYP1A2 inhibition	-	0.5929	59.29%
CYP2C8 inhibition	-	0.6977	69.77%
CYP inhibitory promiscuity	+	0.5000	50.00%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6822	68.22%
Eye corrosion	-	0.9879	98.79%
Eye irritation	-	0.9776	97.76%
Skin irritation	-	0.8161	81.61%
Skin corrosion	-	0.9351	93.51%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8043	80.43%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.5171	51.71%
skin sensitisation	-	0.8626	86.26%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	-	0.6628	66.28%
Acute Oral Toxicity (c)	III	0.5258	52.58%
Estrogen receptor binding	+	0.5307	53.07%
Androgen receptor binding	+	0.7221	72.21%
Thyroid receptor binding	+	0.5667	56.67%
Glucocorticoid receptor binding	-	0.5300	53.00%
Aromatase binding	-	0.5735	57.35%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.9091	90.91%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5903	59.03%
Fish aquatic toxicity	-	0.4144	41.44%

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	98.53%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.80%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.51%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.39%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.10%	97.25%
CHEMBL4208	P20618	Proteasome component C5	88.45%	90.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.91%	91.11%
CHEMBL5028	O14672	ADAM10	85.23%	97.50%
CHEMBL2535	P11166	Glucose transporter	83.98%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.20%	94.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.58%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.34%	95.89%

Plants that contains it

• Aspidosperma pyrifolium

Cross-Links

• PubChem: 162820734
• LOTUS: LTS0159583
• wikiData: Q105228220