(-)-trans-Xylopinine N-oxide

Details

• Internal ID: 69b7862d-95de-4526-b9b5-882a221d0697
• Taxonomy: Alkaloids and derivatives > Protoberberine alkaloids and derivatives
• IUPAC Name: (13aR)-2,3,10,11-tetramethoxy-7-oxido-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinolin-7-ium
• SMILES (Canonical): COC1=C(C=C2C3CC4=CC(=C(C=C4C[N+]3(CCC2=C1)[O-])OC)OC)OC
• SMILES (Isomeric): COC1=C(C=C2[C@H]3CC4=CC(=C(C=C4C[N+]3(CCC2=C1)[O-])OC)OC)OC
• InChI: InChI=1S/C21H25NO5/c1-24-18-8-13-5-6-22(23)12-15-10-20(26-3)19(25-2)9-14(15)7-17(22)16(13)11-21(18)27-4/h8-11,17H,5-7,12H2,1-4H3/t17-,22?/m1/s1
• InChI Key: LXCFBJWUHSPRJQ-PLEWWHCXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₅NO₅
• Molecular Weight: 371.40 g/mol
• Exact Mass: 371.17327290 g/mol
• Topological Polar Surface Area (TPSA): 55.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 3.39
• H-Bond Acceptor: 5
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

• (-)-trans-Xylopinine N-oxide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6839	68.39%
Caco-2	+	0.7376	73.76%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.4727	47.27%
OATP2B1 inhibitior	-	0.8617	86.17%
OATP1B1 inhibitior	+	0.9228	92.28%
OATP1B3 inhibitior	+	0.9432	94.32%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	+	0.6250	62.50%
BSEP inhibitior	-	0.5330	53.30%
P-glycoprotein inhibitior	+	0.7551	75.51%
P-glycoprotein substrate	-	0.6692	66.92%
CYP3A4 substrate	+	0.5334	53.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6720	67.20%
CYP3A4 inhibition	-	0.6426	64.26%
CYP2C9 inhibition	-	0.8484	84.84%
CYP2C19 inhibition	-	0.7427	74.27%
CYP2D6 inhibition	-	0.7154	71.54%
CYP1A2 inhibition	-	0.8525	85.25%
CYP2C8 inhibition	+	0.4514	45.14%
CYP inhibitory promiscuity	-	0.9155	91.55%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8615	86.15%
Carcinogenicity (trinary)	Non-required	0.5408	54.08%
Eye corrosion	-	0.9833	98.33%
Eye irritation	-	0.8324	83.24%
Skin irritation	-	0.7785	77.85%
Skin corrosion	-	0.9354	93.54%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8124	81.24%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.8632	86.32%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6604	66.04%
Acute Oral Toxicity (c)	III	0.6172	61.72%
Estrogen receptor binding	+	0.8907	89.07%
Androgen receptor binding	-	0.5567	55.67%
Thyroid receptor binding	+	0.7273	72.73%
Glucocorticoid receptor binding	+	0.6213	62.13%
Aromatase binding	-	0.5633	56.33%
PPAR gamma	+	0.5689	56.89%
Honey bee toxicity	-	0.7697	76.97%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.7300	73.00%
Fish aquatic toxicity	+	0.6401	64.01%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	96.83%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.78%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.73%	92.94%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.61%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.85%	86.33%
CHEMBL3192	Q9BY41	Histone deacetylase 8	89.91%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.79%	95.89%
CHEMBL2581	P07339	Cathepsin D	85.60%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.84%	99.17%
CHEMBL2535	P11166	Glucose transporter	82.75%	98.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.66%	95.56%
CHEMBL2056	P21728	Dopamine D1 receptor	81.79%	91.00%
CHEMBL217	P14416	Dopamine D2 receptor	81.57%	95.62%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.87%	89.62%

Plants that contains it

• Stephania suberosa

Cross-Links

• PubChem: 163184420
• LOTUS: LTS0029977
• wikiData: Q105158764