Sophocarpidine

Details

• Internal ID: d217890a-6b90-46d0-9de7-3267ce3f85e2
• Taxonomy: Alkaloids and derivatives > Lupin alkaloids > Matrine alkaloids
• IUPAC Name: (1R,2R,9S,13R,17S)-13-oxido-7-aza-13-azoniatetracyclo[7.7.1.02,7.013,17]heptadec-4-en-6-one
• SMILES (Canonical): C1CC2CN3C(CC=CC3=O)C4C2[N+](C1)(CCC4)[O-]
• SMILES (Isomeric): C1C[C@H]2CN3[C@H](CC=CC3=O)[C@@H]4[C@H]2[N@@+](C1)(CCC4)[O-]
• InChI: InChI=1S/C15H22N2O2/c18-14-7-1-6-13-12-5-3-9-17(19)8-2-4-11(15(12)17)10-16(13)14/h1,7,11-13,15H,2-6,8-10H2/t11-,12+,13+,15-,17+/m0/s1
• InChI Key: QMGGMESMCJCABO-JARXUMMXSA-N
• Popularity: 54 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂N₂O₂
• Molecular Weight: 262.35 g/mol
• Exact Mass: 262.168127949 g/mol
• Topological Polar Surface Area (TPSA): 38.40 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.66
• H-Bond Acceptor: 2
• H-Bond Donor: 0
• Rotatable Bonds: 0

Synonyms

• 26904-64-3
• Sophocarpidine
• Sophocarpine N-oxide
• UNII-58BVU7200M
• 58BVU7200M
• Matridin-15-one, 13,14-didehydro-, 1-oxide
• (1R,2R,9S,13R,17S)-13-oxido-7-aza-13-azoniatetracyclo[7.7.1.02,7.013,17]heptadec-4-en-6-one
• (+)-oxysophocarpine
• (+)-SOPHOCARPINE N-OXIDE
• HY-N0746
• MFCD08689951
• MS-23701
• J595.794J
• MATRIDINE-13-ENE-15-ONE 1-OXIDE
• CS-0009778
• 13,14-DIDEHYDROMATRIDIN-15-ONE 1-OXIDE
• Q27261585
• 1H,5H,10H-DIPYRIDO(2,1-F:3',2',1'-IJ)(1,6)NAPHTHYRIDIN-10-ONE, 2,3,6,7,7A,8,13,13A,13B,13C-DECAHYDRO-, 4-OXIDE, (4R,7AS,13AR,13BR,13CS)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6060	60.60%
Caco-2	+	0.8166	81.66%
Blood Brain Barrier	+	0.9250	92.50%
Human oral bioavailability	+	0.7571	75.71%
Subcellular localzation	Plasma membrane	0.4741	47.41%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.9276	92.76%
OATP1B3 inhibitior	+	0.9427	94.27%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.6000	60.00%
BSEP inhibitior	-	0.7548	75.48%
P-glycoprotein inhibitior	-	0.9485	94.85%
P-glycoprotein substrate	-	0.7097	70.97%
CYP3A4 substrate	+	0.5370	53.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8767	87.67%
CYP3A4 inhibition	-	0.7419	74.19%
CYP2C9 inhibition	-	0.8370	83.70%
CYP2C19 inhibition	-	0.7589	75.89%
CYP2D6 inhibition	-	0.8979	89.79%
CYP1A2 inhibition	-	0.7851	78.51%
CYP2C8 inhibition	-	0.9230	92.30%
CYP inhibitory promiscuity	-	0.7632	76.32%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8400	84.00%
Carcinogenicity (trinary)	Non-required	0.4407	44.07%
Eye corrosion	-	0.9707	97.07%
Eye irritation	-	0.7716	77.16%
Skin irritation	-	0.7272	72.72%
Skin corrosion	-	0.9097	90.97%
Ames mutagenesis	-	0.7600	76.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6427	64.27%
Micronuclear	+	0.6200	62.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8384	83.84%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.4669	46.69%
Acute Oral Toxicity (c)	III	0.5871	58.71%
Estrogen receptor binding	-	0.5283	52.83%
Androgen receptor binding	+	0.6390	63.90%
Thyroid receptor binding	-	0.6343	63.43%
Glucocorticoid receptor binding	+	0.5900	59.00%
Aromatase binding	-	0.8315	83.15%
PPAR gamma	-	0.5900	59.00%
Honey bee toxicity	-	0.9188	91.88%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	-	0.7456	74.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	89.67%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.45%	97.09%
CHEMBL1978	P11511	Cytochrome P450 19A1	87.91%	91.76%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.36%	95.56%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	86.88%	93.40%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.61%	82.69%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.14%	92.94%
CHEMBL3384	Q16512	Protein kinase N1	83.87%	80.71%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.20%	93.04%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.17%	92.88%

Plants that contains it

• Ammodendron bifolium
• Sophora alopecuroides
• Sophora davidii
• Sophora flavescens

Cross-Links

• PubChem: 24721085
• NPASS: NPC209200
• LOTUS: LTS0116317
• wikiData: Q27261585