13-Hydroxy-17-oxolupanine

Details

• Internal ID: bc403c6a-7acc-406e-bf55-8a9c1fce01be
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Sparteine, lupanine, and related alkaloids
• IUPAC Name: 13-hydroxy-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecane-6,17-dione
• SMILES (Canonical): C1CC2C3CN4CC(CCC4C(C3=O)CN2C(=O)C1)O
• SMILES (Isomeric): C1CC2C3CN4CC(CCC4C(C3=O)CN2C(=O)C1)O
• InChI: InChI=1S/C15H22N2O3/c18-9-4-5-12-11-8-17-13(2-1-3-14(17)19)10(15(11)20)7-16(12)6-9/h9-13,18H,1-8H2
• InChI Key: GDHIGJBIQZNHST-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂N₂O₃
• Molecular Weight: 278.35 g/mol
• Exact Mass: 278.16304257 g/mol
• Topological Polar Surface Area (TPSA): 60.90 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 0.02
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

• GDHIGJBIQZNHST-UHFFFAOYSA-N

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9460	94.60%
Caco-2	+	0.5771	57.71%
Blood Brain Barrier	+	0.6316	63.16%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8504	85.04%
OATP2B1 inhibitior	-	0.8556	85.56%
OATP1B1 inhibitior	+	0.9136	91.36%
OATP1B3 inhibitior	+	0.9465	94.65%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5750	57.50%
BSEP inhibitior	-	0.7821	78.21%
P-glycoprotein inhibitior	-	0.9330	93.30%
P-glycoprotein substrate	-	0.8131	81.31%
CYP3A4 substrate	+	0.5346	53.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4019	40.19%
CYP3A4 inhibition	-	0.9349	93.49%
CYP2C9 inhibition	-	0.9624	96.24%
CYP2C19 inhibition	-	0.8370	83.70%
CYP2D6 inhibition	-	0.9135	91.35%
CYP1A2 inhibition	-	0.9249	92.49%
CYP2C8 inhibition	-	0.9698	96.98%
CYP inhibitory promiscuity	-	0.9763	97.63%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6660	66.60%
Eye corrosion	-	0.9822	98.22%
Eye irritation	-	0.8796	87.96%
Skin irritation	-	0.7712	77.12%
Skin corrosion	-	0.9172	91.72%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6668	66.68%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.6783	67.83%
skin sensitisation	-	0.9075	90.75%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.4637	46.37%
Acute Oral Toxicity (c)	III	0.5715	57.15%
Estrogen receptor binding	+	0.5855	58.55%
Androgen receptor binding	+	0.6192	61.92%
Thyroid receptor binding	-	0.6297	62.97%
Glucocorticoid receptor binding	-	0.5726	57.26%
Aromatase binding	-	0.7491	74.91%
PPAR gamma	-	0.7372	73.72%
Honey bee toxicity	-	0.9029	90.29%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	-	0.9421	94.21%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	91.38%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.47%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.35%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.70%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.60%	96.09%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	85.21%	93.03%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.91%	90.71%
CHEMBL1902	P62942	FK506-binding protein 1A	83.39%	97.05%
CHEMBL1978	P11511	Cytochrome P450 19A1	83.05%	91.76%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.43%	90.08%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	81.49%	90.24%
CHEMBL217	P14416	Dopamine D2 receptor	81.29%	95.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.39%	95.89%

Plants that contains it

• Lupinus linearis

Cross-Links

• PubChem: 6430122
• LOTUS: LTS0048758
• wikiData: Q104253366