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

Details

• Internal ID: cf2c667d-94c9-49ef-8f5c-0a8a06afd679
• Taxonomy: Alkaloids and derivatives > Aspidofractine alkaloids
• IUPAC Name: (1R,9R,16R,18S,21S)-2,12-diazahexacyclo[14.2.2.19,12.01,9.03,8.016,21]henicosa-3,5,7-triene-18-carboxylic acid
• SMILES (Canonical): C1CC23CCC4(C(C2)C(=O)O)C5(C3N(C1)CC5)C6=CC=CC=C6N4
• SMILES (Isomeric): C1C[C@@]23CC[C@@]4([C@H](C2)C(=O)O)[C@@]5([C@H]3N(C1)CC5)C6=CC=CC=C6N4
• InChI: InChI=1S/C20H24N2O2/c23-16(24)14-12-18-6-3-10-22-11-9-19(17(18)22)13-4-1-2-5-15(13)21-20(14,19)8-7-18/h1-2,4-5,14,17,21H,3,6-12H2,(H,23,24)/t14-,17+,18-,19-,20-/m1/s1
• InChI Key: AZPTZMIACWMVSO-PBOLBBRVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄N₂O₂
• Molecular Weight: 324.40 g/mol
• Exact Mass: 324.183778013 g/mol
• Topological Polar Surface Area (TPSA): 52.60 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 2.84
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9390	93.90%
Caco-2	+	0.6160	61.60%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.6200	62.00%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.9233	92.33%
OATP1B3 inhibitior	+	0.9453	94.53%
MATE1 inhibitior	-	0.8809	88.09%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.7045	70.45%
P-glycoprotein inhibitior	-	0.9241	92.41%
P-glycoprotein substrate	-	0.6785	67.85%
CYP3A4 substrate	+	0.5786	57.86%
CYP2C9 substrate	-	0.7752	77.52%
CYP2D6 substrate	+	0.4236	42.36%
CYP3A4 inhibition	-	0.8628	86.28%
CYP2C9 inhibition	-	0.9085	90.85%
CYP2C19 inhibition	-	0.9162	91.62%
CYP2D6 inhibition	-	0.7604	76.04%
CYP1A2 inhibition	-	0.6827	68.27%
CYP2C8 inhibition	-	0.8537	85.37%
CYP inhibitory promiscuity	-	0.9236	92.36%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6735	67.35%
Eye corrosion	-	0.9873	98.73%
Eye irritation	-	0.9882	98.82%
Skin irritation	-	0.7367	73.67%
Skin corrosion	-	0.9342	93.42%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5807	58.07%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8547	85.47%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.6442	64.42%
Acute Oral Toxicity (c)	III	0.4661	46.61%
Estrogen receptor binding	-	0.5532	55.32%
Androgen receptor binding	+	0.7438	74.38%
Thyroid receptor binding	-	0.5951	59.51%
Glucocorticoid receptor binding	-	0.5000	50.00%
Aromatase binding	+	0.6101	61.01%
PPAR gamma	+	0.5374	53.74%
Honey bee toxicity	-	0.9186	91.86%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.6999	69.99%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4208	P20618	Proteasome component C5	91.62%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.96%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.94%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.45%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.95%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.23%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.17%	99.23%
CHEMBL5028	O14672	ADAM10	82.81%	97.50%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.01%	93.03%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.21%	100.00%

Plants that contains it

• Kopsia hainanensis

Cross-Links

• PubChem: 162924422
• LOTUS: LTS0207401
• wikiData: Q104921859