[(1S,2S,4S,9S,10R)-14-oxo-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecan-4-yl] (E,3R)-3-hydroxyoct-5-enoate

Details

• Internal ID: 4f183a7a-c2af-4d5c-b02e-a8e14e230f5a
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Sparteine, lupanine, and related alkaloids
• IUPAC Name: [(1S,2S,4S,9S,10R)-14-oxo-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecan-4-yl] (E,3R)-3-hydroxyoct-5-enoate
• SMILES (Canonical): CCC=CCC(CC(=O)OC1CCN2CC3CC(C2C1)CN4C3CCCC4=O)O
• SMILES (Isomeric): CC/C=C/C[C@H](CC(=O)O[C@H]1CCN2C[C@@H]3C[C@H]([C@@H]2C1)CN4[C@@H]3CCCC4=O)O
• InChI: InChI=1S/C23H36N2O4/c1-2-3-4-6-18(26)12-23(28)29-19-9-10-24-14-16-11-17(21(24)13-19)15-25-20(16)7-5-8-22(25)27/h3-4,16-21,26H,2,5-15H2,1H3/b4-3+/t16-,17-,18+,19-,20+,21-/m0/s1
• InChI Key: COEBHSNHYKFGAA-DMFCBCPGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₆N₂O₄
• Molecular Weight: 404.50 g/mol
• Exact Mass: 404.26750763 g/mol
• Topological Polar Surface Area (TPSA): 70.10 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.50
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9447	94.47%
Caco-2	-	0.5746	57.46%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7106	71.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8688	86.88%
OATP1B3 inhibitior	+	0.9378	93.78%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.8028	80.28%
P-glycoprotein inhibitior	-	0.5241	52.41%
P-glycoprotein substrate	+	0.6325	63.25%
CYP3A4 substrate	+	0.6472	64.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7410	74.10%
CYP3A4 inhibition	-	0.8463	84.63%
CYP2C9 inhibition	-	0.9190	91.90%
CYP2C19 inhibition	-	0.8593	85.93%
CYP2D6 inhibition	-	0.9326	93.26%
CYP1A2 inhibition	-	0.8888	88.88%
CYP2C8 inhibition	-	0.7925	79.25%
CYP inhibitory promiscuity	-	0.8586	85.86%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5591	55.91%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9270	92.70%
Skin irritation	-	0.8169	81.69%
Skin corrosion	-	0.9469	94.69%
Ames mutagenesis	-	0.7419	74.19%
Human Ether-a-go-go-Related Gene inhibition	-	0.3622	36.22%
Micronuclear	+	0.7200	72.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8851	88.51%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.6952	69.52%
Acute Oral Toxicity (c)	III	0.7186	71.86%
Estrogen receptor binding	+	0.5641	56.41%
Androgen receptor binding	+	0.5477	54.77%
Thyroid receptor binding	-	0.6175	61.75%
Glucocorticoid receptor binding	+	0.5916	59.16%
Aromatase binding	-	0.5872	58.72%
PPAR gamma	-	0.5753	57.53%
Honey bee toxicity	-	0.8993	89.93%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.5985	59.85%

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	98.75%	96.09%
CHEMBL2581	P07339	Cathepsin D	97.03%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.05%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.94%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.93%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.86%	97.09%
CHEMBL321	P14780	Matrix metalloproteinase 9	90.29%	92.12%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.25%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	87.40%	91.19%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.83%	96.47%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	86.07%	98.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.14%	99.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	84.96%	95.50%
CHEMBL4588	P22894	Matrix metalloproteinase 8	84.41%	94.66%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	84.27%	91.43%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	83.99%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.80%	95.89%
CHEMBL5255	O00206	Toll-like receptor 4	83.63%	92.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.96%	94.33%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.37%	100.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.28%	90.08%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.83%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.62%	86.33%

Plants that contains it

• Genista pilosa

Cross-Links

• PubChem: 15939892
• LOTUS: LTS0044410
• wikiData: Q105102983