(13R,15S,16S,18R)-15-ethyl-11-methyl-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-4(12),5,7,9-tetraen-13-ol

Details

• Internal ID: 528e216c-44c1-481a-a5d2-0b462b66caaa
• Taxonomy: Alkaloids and derivatives > Quebrachamine alkaloids
• IUPAC Name: (13R,15S,16S,18R)-15-ethyl-11-methyl-17-oxa-1,11-diazapentacyclo[13.4.1.04,12.05,10.016,18]icosa-4(12),5,7,9-tetraen-13-ol
• InChI: InChI=1S/C20H26N2O2/c1-3-20-10-16(23)18-14(13-6-4-5-7-15(13)21(18)2)8-9-22(12-20)11-17-19(20)24-17/h4-7,16-17,19,23H,3,8-12H2,1-2H3/t16-,17-,19-,20+/m1/s1
• InChI Key: XXXZUQSJLJCVOM-LFGUQSLTSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₆N₂O₂
• Molecular Weight: 326.40 g/mol
• Exact Mass: 326.199428076 g/mol
• Topological Polar Surface Area (TPSA): 40.90 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.64
• 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	+	0.9609	96.09%
Caco-2	+	0.8837	88.37%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Lysosomes	0.6175	61.75%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9231	92.31%
OATP1B3 inhibitior	+	0.9458	94.58%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.7836	78.36%
P-glycoprotein inhibitior	-	0.6792	67.92%
P-glycoprotein substrate	+	0.6092	60.92%
CYP3A4 substrate	+	0.6617	66.17%
CYP2C9 substrate	-	0.8075	80.75%
CYP2D6 substrate	+	0.4607	46.07%
CYP3A4 inhibition	-	0.8244	82.44%
CYP2C9 inhibition	-	0.9076	90.76%
CYP2C19 inhibition	-	0.8059	80.59%
CYP2D6 inhibition	-	0.6468	64.68%
CYP1A2 inhibition	-	0.8467	84.67%
CYP2C8 inhibition	-	0.7901	79.01%
CYP inhibitory promiscuity	-	0.9107	91.07%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6798	67.98%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9959	99.59%
Skin irritation	-	0.8055	80.55%
Skin corrosion	-	0.9248	92.48%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8331	83.31%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.5836	58.36%
skin sensitisation	-	0.8314	83.14%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.7917	79.17%
Acute Oral Toxicity (c)	III	0.5733	57.33%
Estrogen receptor binding	+	0.5832	58.32%
Androgen receptor binding	+	0.5311	53.11%
Thyroid receptor binding	+	0.7023	70.23%
Glucocorticoid receptor binding	+	0.6091	60.91%
Aromatase binding	+	0.5245	52.45%
PPAR gamma	-	0.4898	48.98%
Honey bee toxicity	-	0.9232	92.32%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	-	0.6787	67.87%

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	98.67%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.09%	97.25%
CHEMBL3192	Q9BY41	Histone deacetylase 8	96.09%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.38%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.05%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.27%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.50%	89.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.00%	91.11%
CHEMBL2581	P07339	Cathepsin D	84.33%	98.95%
CHEMBL255	P29275	Adenosine A2b receptor	81.91%	98.59%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	81.57%	93.65%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.92%	90.08%

Plants that contains it

• Tabernaemontana divaricata

Cross-Links

• PubChem: 11759202
• LOTUS: LTS0130379
• wikiData: Q105344277