(1S,9R,16R,18S,21S)-2,12-diazahexacyclo[14.2.2.19,12.01,9.03,8.016,21]henicosa-3,5,7-trien-18-ol

Details

• Internal ID: b649eb79-ce10-4fdd-9727-d0f57f98a6d4
• Taxonomy: Alkaloids and derivatives > Aspidofractine alkaloids
• IUPAC Name: (1S,9R,16R,18S,21S)-2,12-diazahexacyclo[14.2.2.19,12.01,9.03,8.016,21]henicosa-3,5,7-trien-18-ol
• SMILES (Canonical): C1CC23CCC4(C(C2)O)C5(C3N(C1)CC5)C6=CC=CC=C6N4
• SMILES (Isomeric): C1C[C@@]23CC[C@@]4([C@H](C2)O)[C@@]5([C@H]3N(C1)CC5)C6=CC=CC=C6N4
• InChI: InChI=1S/C19H24N2O/c22-15-12-17-6-3-10-21-11-9-18(16(17)21)13-4-1-2-5-14(13)20-19(15,18)8-7-17/h1-2,4-5,15-16,20,22H,3,6-12H2/t15-,16-,17+,18+,19+/m0/s1
• InChI Key: ZEEUPFDTVPGHSL-NTZUZEMLSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₄N₂O
• Molecular Weight: 296.40 g/mol
• Exact Mass: 296.188863393 g/mol
• Topological Polar Surface Area (TPSA): 35.50 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.50
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9719	97.19%
Caco-2	+	0.7482	74.82%
Blood Brain Barrier	+	0.9257	92.57%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6595	65.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9285	92.85%
OATP1B3 inhibitior	+	0.9511	95.11%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	-	0.6795	67.95%
P-glycoprotein inhibitior	-	0.9616	96.16%
P-glycoprotein substrate	-	0.5996	59.96%
CYP3A4 substrate	+	0.5568	55.68%
CYP2C9 substrate	+	0.5735	57.35%
CYP2D6 substrate	+	0.6260	62.60%
CYP3A4 inhibition	-	0.9380	93.80%
CYP2C9 inhibition	-	0.8992	89.92%
CYP2C19 inhibition	-	0.8825	88.25%
CYP2D6 inhibition	+	0.6427	64.27%
CYP1A2 inhibition	-	0.7154	71.54%
CYP2C8 inhibition	-	0.8524	85.24%
CYP inhibitory promiscuity	-	0.9076	90.76%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6588	65.88%
Eye corrosion	-	0.9826	98.26%
Eye irritation	-	0.9942	99.42%
Skin irritation	-	0.6978	69.78%
Skin corrosion	-	0.8472	84.72%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6466	64.66%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	+	0.5293	52.93%
skin sensitisation	-	0.8199	81.99%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.7552	75.52%
Acute Oral Toxicity (c)	III	0.5388	53.88%
Estrogen receptor binding	+	0.5473	54.73%
Androgen receptor binding	+	0.7351	73.51%
Thyroid receptor binding	+	0.5874	58.74%
Glucocorticoid receptor binding	-	0.6499	64.99%
Aromatase binding	+	0.5355	53.55%
PPAR gamma	+	0.5580	55.80%
Honey bee toxicity	-	0.8972	89.72%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	-	0.7764	77.64%

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	91.91%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.24%	95.56%
CHEMBL4208	P20618	Proteasome component C5	89.48%	90.00%
CHEMBL2581	P07339	Cathepsin D	89.25%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.86%	91.11%
CHEMBL3155	P34969	Serotonin 7 (5-HT7) receptor	84.60%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.32%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.40%	93.03%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.21%	94.62%
CHEMBL238	Q01959	Dopamine transporter	82.11%	95.88%
CHEMBL221	P23219	Cyclooxygenase-1	81.71%	90.17%
CHEMBL5805	Q9NR97	Toll-like receptor 8	80.83%	96.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.63%	97.09%

Plants that contains it

• Kopsia arborea

Cross-Links

• PubChem: 163099490
• LOTUS: LTS0251453
• wikiData: Q105373161