8-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-1-hydroxy-5-methoxy-3-methyl-6-[(3S)-2-oxopiperidin-3-yl]-5H-benzo[b]phenanthridine-7,12-dione

Details

• Internal ID: 5cb081e5-8ce9-4414-bf38-b38507126e96
• Taxonomy: Alkaloids and derivatives > Protopine alkaloids
• IUPAC Name: 8-[(2S,4R,5R,6S)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-1-hydroxy-5-methoxy-3-methyl-6-[(3S)-2-oxopiperidin-3-yl]-5H-benzo[b]phenanthridine-7,12-dione
• SMILES (Canonical): CC1C(C(CC(O1)OC2=CC=CC3=C2C(=O)C4=C(C3=O)C5=C(C=C(C=C5O)C)C(N4C6CCCNC6=O)OC)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@@H](C[C@@H](O1)OC2=CC=CC3=C2C(=O)C4=C(C3=O)C5=C(C=C(C=C5O)C)C(N4[C@H]6CCCNC6=O)OC)O)O
• InChI: InChI=1S/C30H32N2O9/c1-13-10-16-22(18(33)11-13)24-25(32(30(16)39-3)17-7-5-9-31-29(17)38)28(37)23-15(27(24)36)6-4-8-20(23)41-21-12-19(34)26(35)14(2)40-21/h4,6,8,10-11,14,17,19,21,26,30,33-35H,5,7,9,12H2,1-3H3,(H,31,38)/t14-,17-,19+,21-,26-,30?/m0/s1
• InChI Key: MCJNSBWQSXKPCQ-LJTNYANWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₂N₂O₉
• Molecular Weight: 564.60 g/mol
• Exact Mass: 564.21078060 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 1.97
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5274	52.74%
Caco-2	-	0.8244	82.44%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6456	64.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8619	86.19%
OATP1B3 inhibitior	+	0.9238	92.38%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8061	80.61%
BSEP inhibitior	+	0.8545	85.45%
P-glycoprotein inhibitior	+	0.6733	67.33%
P-glycoprotein substrate	+	0.6908	69.08%
CYP3A4 substrate	+	0.7174	71.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8689	86.89%
CYP3A4 inhibition	-	0.7256	72.56%
CYP2C9 inhibition	-	0.7357	73.57%
CYP2C19 inhibition	-	0.8420	84.20%
CYP2D6 inhibition	-	0.8901	89.01%
CYP1A2 inhibition	-	0.8555	85.55%
CYP2C8 inhibition	+	0.5712	57.12%
CYP inhibitory promiscuity	-	0.9387	93.87%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.5354	53.54%
Eye corrosion	-	0.9845	98.45%
Eye irritation	-	0.9501	95.01%
Skin irritation	-	0.7608	76.08%
Skin corrosion	-	0.9291	92.91%
Ames mutagenesis	+	0.5946	59.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.4088	40.88%
Micronuclear	+	0.7900	79.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8674	86.74%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.6052	60.52%
Acute Oral Toxicity (c)	III	0.5812	58.12%
Estrogen receptor binding	+	0.7420	74.20%
Androgen receptor binding	+	0.7374	73.74%
Thyroid receptor binding	-	0.5147	51.47%
Glucocorticoid receptor binding	+	0.7734	77.34%
Aromatase binding	-	0.5798	57.98%
PPAR gamma	+	0.6563	65.63%
Honey bee toxicity	-	0.7776	77.76%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8238	82.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	99.52%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.38%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.90%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	97.68%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.42%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.16%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	96.33%	91.49%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.24%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.93%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.34%	86.33%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	94.05%	93.03%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.75%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	90.50%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.43%	100.00%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	88.99%	96.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.37%	90.71%
CHEMBL2095226	P05556	Integrin alpha-5/beta-1	88.36%	96.39%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	88.31%	95.64%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.25%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.23%	97.14%
CHEMBL2535	P11166	Glucose transporter	87.99%	98.75%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	87.09%	91.03%
CHEMBL2056	P21728	Dopamine D1 receptor	86.74%	91.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.13%	96.38%
CHEMBL1902	P62942	FK506-binding protein 1A	85.92%	97.05%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	84.76%	100.00%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	84.17%	83.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	83.03%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.79%	92.94%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.40%	96.21%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	82.07%	96.67%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.08%	93.40%

Plants that contains it

• Hypericum ascyron

Cross-Links

• PubChem: 139589544
• LOTUS: LTS0115548
• wikiData: Q105144795