(1R,2R,9R,17S)-7,13-Diazatetracyclo[7.7.1.02,7.013,17]heptadec-4-en-6-one

Details

• Internal ID: 7bbd3c5a-969a-47d1-a026-3447e9717d14
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Matrine alkaloids
• IUPAC Name: (1R,2R,9R,17S)-7,13-diazatetracyclo[7.7.1.02,7.013,17]heptadec-4-en-6-one
• SMILES (Canonical): C1CC2CN3C(CC=CC3=O)C4C2N(C1)CCC4
• SMILES (Isomeric): C1C[C@@H]2CN3[C@H](CC=CC3=O)[C@@H]4[C@H]2N(C1)CCC4
• InChI: InChI=1S/C15H22N2O/c18-14-7-1-6-13-12-5-3-9-16-8-2-4-11(15(12)16)10-17(13)14/h1,7,11-13,15H,2-6,8-10H2/t11-,12-,13-,15+/m1/s1
• InChI Key: AAGFPTSOPGCENQ-BHPKHCPMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂N₂O
• Molecular Weight: 246.35 g/mol
• Exact Mass: 246.173213330 g/mol
• Topological Polar Surface Area (TPSA): 23.60 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.65
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• (1R,2R,9R,17S)-7,13-Diazatetracyclo[7.7.1.02,7.013,17]heptadec-4-en-6-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9885	98.85%
Caco-2	+	0.9200	92.00%
Blood Brain Barrier	+	0.9750	97.50%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.5101	51.01%
OATP2B1 inhibitior	-	0.8585	85.85%
OATP1B1 inhibitior	+	0.9421	94.21%
OATP1B3 inhibitior	+	0.9518	95.18%
MATE1 inhibitior	-	0.9209	92.09%
OCT2 inhibitior	+	0.8250	82.50%
BSEP inhibitior	-	0.7512	75.12%
P-glycoprotein inhibitior	-	0.9482	94.82%
P-glycoprotein substrate	-	0.7438	74.38%
CYP3A4 substrate	+	0.5118	51.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7702	77.02%
CYP3A4 inhibition	-	0.9310	93.10%
CYP2C9 inhibition	-	0.9005	90.05%
CYP2C19 inhibition	-	0.7025	70.25%
CYP2D6 inhibition	-	0.9136	91.36%
CYP1A2 inhibition	-	0.7062	70.62%
CYP2C8 inhibition	-	0.9514	95.14%
CYP inhibitory promiscuity	-	0.6415	64.15%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6175	61.75%
Eye corrosion	-	0.9027	90.27%
Eye irritation	-	0.7012	70.12%
Skin irritation	-	0.6244	62.44%
Skin corrosion	-	0.8953	89.53%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6629	66.29%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.7625	76.25%
skin sensitisation	-	0.8751	87.51%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6956	69.56%
Acute Oral Toxicity (c)	II	0.7391	73.91%
Estrogen receptor binding	-	0.8079	80.79%
Androgen receptor binding	-	0.5385	53.85%
Thyroid receptor binding	-	0.6787	67.87%
Glucocorticoid receptor binding	-	0.6222	62.22%
Aromatase binding	-	0.8303	83.03%
PPAR gamma	-	0.6799	67.99%
Honey bee toxicity	-	0.8822	88.22%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	-	0.7681	76.81%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	90.68%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.87%	93.40%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.19%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.12%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.71%	95.56%
CHEMBL3384	Q16512	Protein kinase N1	86.16%	80.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.79%	95.89%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	83.94%	90.24%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.77%	97.25%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.41%	93.04%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.80%	93.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.67%	100.00%
CHEMBL264	Q9Y5N1	Histamine H3 receptor	80.10%	91.43%

Plants that contains it

• Asimina parviflora
• Atraphaxis spinosa
• Baccharis neglecta
• Centaurea cuneifolia subsp. cuneifolia
• Chondrodendron tomentosum
• Clerodendrum bungei
• Diospyros ebenum
• Embelia parviflora
• Embelia schimperi
• Ephedra sinica
• Epilobium hirsutum
• Erysimum leptophyllum
• Erythrina melanacantha
• Esenbeckia leiocarpa
• Euphorbia jolkinii
• Faramea multiflora
• Gymnocalycium schickendantzii
• Haplophyllum obtusifolium
• Helichrysum tenuifolium
• Hypericum styphelioides
• Linnaea chinensis
• Lythrum salicaria
• Monsonia senegalensis
• Myrica rubra
• Onopordum acanthium
• Pancratium sickenbergeri
• Pinalia anomala
• Piper regnellii
• Plathymenia reticulata
• Pteridium esculentum
• Simarouba glauca
• Sophora flavescens
• Stenocereus laevigatus
• Syzygium polycephaloides
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 21763818
• NPASS: NPC120699
• LOTUS: LTS0195595
• wikiData: Q104907902