methyl (1S,9S,16S,18S,21R)-12-oxido-2-aza-12-azoniahexacyclo[14.2.2.19,12.01,9.03,8.016,21]henicosa-3,5,7-triene-18-carboxylate

Details

• Internal ID: c65501fc-4dc9-4bdb-ad70-a5bc53ea0bf1
• Taxonomy: Alkaloids and derivatives > Aspidofractine alkaloids
• IUPAC Name: methyl (1S,9S,16S,18S,21R)-12-oxido-2-aza-12-azoniahexacyclo[14.2.2.19,12.01,9.03,8.016,21]henicosa-3,5,7-triene-18-carboxylate
• SMILES (Canonical): COC(=O)C1CC23CCC[N+]4(C2C5(C1(CC3)NC6=CC=CC=C65)CC4)[O-]
• SMILES (Isomeric): COC(=O)[C@H]1C[C@@]23CCC[N+]4([C@H]2[C@]5([C@@]1(CC3)NC6=CC=CC=C65)CC4)[O-]
• InChI: InChI=1S/C21H26N2O3/c1-26-17(24)15-13-19-7-4-11-23(25)12-10-20(18(19)23)14-5-2-3-6-16(14)22-21(15,20)9-8-19/h2-3,5-6,15,18,22H,4,7-13H2,1H3/t15-,18-,19+,20+,21+,23?/m1/s1
• InChI Key: KWXHCCIXBUPHTG-KSDLINPOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆N₂O₃
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.19434270 g/mol
• Topological Polar Surface Area (TPSA): 56.40 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.94
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7029	70.29%
Caco-2	+	0.6526	65.26%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Lysosomes	0.4975	49.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8943	89.43%
OATP1B3 inhibitior	+	0.9370	93.70%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.5969	59.69%
P-glycoprotein inhibitior	-	0.8246	82.46%
P-glycoprotein substrate	-	0.5375	53.75%
CYP3A4 substrate	+	0.6441	64.41%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.7852	78.52%
CYP3A4 inhibition	-	0.7050	70.50%
CYP2C9 inhibition	-	0.8316	83.16%
CYP2C19 inhibition	-	0.8165	81.65%
CYP2D6 inhibition	-	0.7128	71.28%
CYP1A2 inhibition	-	0.7208	72.08%
CYP2C8 inhibition	+	0.4545	45.45%
CYP inhibitory promiscuity	-	0.9215	92.15%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5665	56.65%
Eye corrosion	-	0.9813	98.13%
Eye irritation	-	0.9842	98.42%
Skin irritation	-	0.7662	76.62%
Skin corrosion	-	0.9290	92.90%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4056	40.56%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.8402	84.02%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.5929	59.29%
Acute Oral Toxicity (c)	III	0.5455	54.55%
Estrogen receptor binding	+	0.6803	68.03%
Androgen receptor binding	+	0.7501	75.01%
Thyroid receptor binding	+	0.5790	57.90%
Glucocorticoid receptor binding	+	0.6229	62.29%
Aromatase binding	+	0.6645	66.45%
PPAR gamma	-	0.5304	53.04%
Honey bee toxicity	-	0.8917	89.17%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5700	57.00%
Fish aquatic toxicity	+	0.8003	80.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.92%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.92%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.46%	95.56%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.92%	93.03%
CHEMBL4040	P28482	MAP kinase ERK2	85.13%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.93%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.61%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.69%	99.23%
CHEMBL2581	P07339	Cathepsin D	83.40%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.16%	94.45%

Plants that contains it

• Kopsia hainanensis
• Pleiocarpa pycnantha

Cross-Links

• PubChem: 163188227
• LOTUS: LTS0253444
• wikiData: Q105147202