1-[(9R,21S)-4-hydroxy-2,12-diazahexacyclo[14.2.2.19,12.01,9.03,8.016,21]henicosa-3(8),4,6-trien-2-yl]ethanone

Details

• Internal ID: 5fbede91-507e-43e3-a6da-e85b9ccab46a
• Taxonomy: Alkaloids and derivatives > Aspidofractine alkaloids
• IUPAC Name: 1-[(9R,21S)-4-hydroxy-2,12-diazahexacyclo[14.2.2.19,12.01,9.03,8.016,21]henicosa-3(8),4,6-trien-2-yl]ethanone
• SMILES (Canonical): CC(=O)N1C2=C(C=CC=C2O)C34C15CCC6(C3N(CCC6)CC4)CC5
• SMILES (Isomeric): CC(=O)N1C2=C(C=CC=C2O)[C@@]34C15CCC6([C@@H]3N(CCC6)CC4)CC5
• InChI: InChI=1S/C21H26N2O2/c1-14(24)23-17-15(4-2-5-16(17)25)21-11-13-22-12-3-6-19(18(21)22)7-9-20(21,23)10-8-19/h2,4-5,18,25H,3,6-13H2,1H3/t18-,19?,20?,21+/m0/s1
• InChI Key: OPMCYTBHMYQBKH-GKYDQMIMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆N₂O₂
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.199428076 g/mol
• Topological Polar Surface Area (TPSA): 43.80 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 3.18
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9846	98.46%
Caco-2	+	0.6476	64.76%
Blood Brain Barrier	+	0.8817	88.17%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7447	74.47%
OATP2B1 inhibitior	-	0.8604	86.04%
OATP1B1 inhibitior	+	0.9287	92.87%
OATP1B3 inhibitior	+	0.9493	94.93%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	+	0.6750	67.50%
BSEP inhibitior	-	0.5645	56.45%
P-glycoprotein inhibitior	-	0.8760	87.60%
P-glycoprotein substrate	-	0.5315	53.15%
CYP3A4 substrate	+	0.6152	61.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3931	39.31%
CYP3A4 inhibition	+	0.8001	80.01%
CYP2C9 inhibition	-	0.8735	87.35%
CYP2C19 inhibition	-	0.6903	69.03%
CYP2D6 inhibition	+	0.5329	53.29%
CYP1A2 inhibition	+	0.5543	55.43%
CYP2C8 inhibition	-	0.8188	81.88%
CYP inhibitory promiscuity	+	0.5976	59.76%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6516	65.16%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9614	96.14%
Skin irritation	-	0.8076	80.76%
Skin corrosion	-	0.9224	92.24%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5325	53.25%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.7052	70.52%
skin sensitisation	-	0.8515	85.15%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.6179	61.79%
Acute Oral Toxicity (c)	III	0.4697	46.97%
Estrogen receptor binding	-	0.4853	48.53%
Androgen receptor binding	+	0.7415	74.15%
Thyroid receptor binding	+	0.5891	58.91%
Glucocorticoid receptor binding	+	0.5689	56.89%
Aromatase binding	-	0.5635	56.35%
PPAR gamma	+	0.6868	68.68%
Honey bee toxicity	-	0.9462	94.62%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6051	60.51%
Fish aquatic toxicity	-	0.4619	46.19%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.74%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.44%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.32%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.61%	91.11%
CHEMBL4208	P20618	Proteasome component C5	85.54%	90.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.03%	93.03%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.85%	86.33%
CHEMBL5028	O14672	ADAM10	83.49%	97.50%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.19%	90.71%
CHEMBL233	P35372	Mu opioid receptor	82.03%	97.93%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.56%	93.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.33%	97.25%

Plants that contains it

• Aspidosperma pyrifolium

Cross-Links

• PubChem: 22215835
• LOTUS: LTS0238254
• wikiData: Q104394995