(1R,2R,5S,9S,17S)-5-hydroxy-13-oxido-7-aza-13-azoniatetracyclo[7.7.1.02,7.013,17]heptadecan-6-one

Details

• Internal ID: 18fafd75-9ef0-42cb-a4df-8a17a666c7ca
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Matrine alkaloids
• IUPAC Name: (1R,2R,5S,9S,17S)-5-hydroxy-13-oxido-7-aza-13-azoniatetracyclo[7.7.1.02,7.013,17]heptadecan-6-one
• SMILES (Canonical): C1CC2CN3C(CCC(C3=O)O)C4C2[N+](C1)(CCC4)[O-]
• SMILES (Isomeric): C1C[C@H]2CN3[C@H](CC[C@@H](C3=O)O)[C@@H]4[C@H]2[N+](C1)(CCC4)[O-]
• InChI: InChI=1S/C15H24N2O3/c18-13-6-5-12-11-4-2-8-17(20)7-1-3-10(14(11)17)9-16(12)15(13)19/h10-14,18H,1-9H2/t10-,11+,12+,13-,14-,17?/m0/s1
• InChI Key: NXUSOOFNXQATTQ-NUEVAWMNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₄N₂O₃
• Molecular Weight: 280.36 g/mol
• Exact Mass: 280.17869263 g/mol
• Topological Polar Surface Area (TPSA): 58.60 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.86
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5755	57.55%
Caco-2	+	0.5108	51.08%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.6524	65.24%
OATP2B1 inhibitior	-	0.8543	85.43%
OATP1B1 inhibitior	+	0.9203	92.03%
OATP1B3 inhibitior	+	0.9412	94.12%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.9031	90.31%
P-glycoprotein inhibitior	-	0.9522	95.22%
P-glycoprotein substrate	-	0.7660	76.60%
CYP3A4 substrate	+	0.5124	51.24%
CYP2C9 substrate	-	0.7965	79.65%
CYP2D6 substrate	-	0.8284	82.84%
CYP3A4 inhibition	-	0.8449	84.49%
CYP2C9 inhibition	-	0.8757	87.57%
CYP2C19 inhibition	-	0.8119	81.19%
CYP2D6 inhibition	-	0.8464	84.64%
CYP1A2 inhibition	-	0.8417	84.17%
CYP2C8 inhibition	-	0.9369	93.69%
CYP inhibitory promiscuity	-	0.9610	96.10%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.4905	49.05%
Eye corrosion	-	0.9796	97.96%
Eye irritation	-	0.8202	82.02%
Skin irritation	-	0.7420	74.20%
Skin corrosion	-	0.9098	90.98%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6019	60.19%
Micronuclear	+	0.6800	68.00%
Hepatotoxicity	+	0.6750	67.50%
skin sensitisation	-	0.8406	84.06%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5823	58.23%
Acute Oral Toxicity (c)	III	0.6039	60.39%
Estrogen receptor binding	+	0.7011	70.11%
Androgen receptor binding	+	0.6721	67.21%
Thyroid receptor binding	-	0.5276	52.76%
Glucocorticoid receptor binding	-	0.4651	46.51%
Aromatase binding	-	0.7943	79.43%
PPAR gamma	-	0.7851	78.51%
Honey bee toxicity	-	0.9235	92.35%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	-	0.8820	88.20%

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	91.68%	83.82%
CHEMBL2581	P07339	Cathepsin D	90.18%	98.95%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	88.23%	93.03%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.17%	92.94%
CHEMBL1978	P11511	Cytochrome P450 19A1	86.67%	91.76%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.63%	95.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.27%	93.04%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.21%	97.09%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	86.11%	94.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.56%	99.23%
CHEMBL1902	P62942	FK506-binding protein 1A	85.22%	97.05%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.13%	93.00%

Plants that contains it

• Sophora tonkinensis

Cross-Links

• PubChem: 12000482
• NPASS: NPC247714