(23S)-12-methoxy-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21)-octaen-23-ol

Details

• Internal ID: 9f942db0-b8f2-4b9e-972e-287153a66d8f
• Taxonomy: Alkaloids and derivatives > Benzophenanthridine alkaloids > Dihydrobenzophenanthridine alkaloids
• IUPAC Name: (23S)-12-methoxy-24-methyl-5,7,18,20-tetraoxa-24-azahexacyclo[11.11.0.02,10.04,8.014,22.017,21]tetracosa-1(13),2,4(8),9,11,14(22),15,17(21)-octaen-23-ol
• SMILES (Canonical): CN1C(C2=C(C=CC3=C2OCO3)C4=C1C5=CC6=C(C=C5C=C4OC)OCO6)O
• SMILES (Isomeric): CN1[C@H](C2=C(C=CC3=C2OCO3)C4=C1C5=CC6=C(C=C5C=C4OC)OCO6)O
• InChI: InChI=1S/C21H17NO6/c1-22-19-12-7-15-14(26-8-27-15)5-10(12)6-16(24-2)17(19)11-3-4-13-20(28-9-25-13)18(11)21(22)23/h3-7,21,23H,8-9H2,1-2H3/t21-/m0/s1
• InChI Key: QRCWKBAFKDYSFR-NRFANRHFSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₇NO₆
• Molecular Weight: 379.40 g/mol
• Exact Mass: 379.10558726 g/mol
• Topological Polar Surface Area (TPSA): 69.60 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.41
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8345	83.45%
Caco-2	+	0.7657	76.57%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.3832	38.32%
OATP2B1 inhibitior	-	0.8664	86.64%
OATP1B1 inhibitior	+	0.9102	91.02%
OATP1B3 inhibitior	+	0.9495	94.95%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9095	90.95%
P-glycoprotein inhibitior	+	0.6010	60.10%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.5910	59.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3479	34.79%
CYP3A4 inhibition	+	0.7155	71.55%
CYP2C9 inhibition	-	0.7474	74.74%
CYP2C19 inhibition	+	0.7316	73.16%
CYP2D6 inhibition	+	0.5453	54.53%
CYP1A2 inhibition	+	0.5797	57.97%
CYP2C8 inhibition	-	0.5812	58.12%
CYP inhibitory promiscuity	+	0.6117	61.17%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4614	46.14%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9496	94.96%
Skin irritation	-	0.8065	80.65%
Skin corrosion	-	0.9507	95.07%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4667	46.67%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	-	0.5177	51.77%
skin sensitisation	-	0.8628	86.28%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.6506	65.06%
Acute Oral Toxicity (c)	III	0.7425	74.25%
Estrogen receptor binding	+	0.7910	79.10%
Androgen receptor binding	+	0.6794	67.94%
Thyroid receptor binding	+	0.6413	64.13%
Glucocorticoid receptor binding	+	0.8332	83.32%
Aromatase binding	+	0.5554	55.54%
PPAR gamma	+	0.7660	76.60%
Honey bee toxicity	-	0.8262	82.62%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.7138	71.38%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.35%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.22%	96.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	94.77%	92.62%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	94.68%	89.62%
CHEMBL2581	P07339	Cathepsin D	92.20%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.15%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.48%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.10%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	90.50%	83.82%
CHEMBL4208	P20618	Proteasome component C5	89.64%	90.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	89.52%	82.67%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.23%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	87.41%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.03%	95.89%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	87.01%	97.31%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.81%	89.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.48%	95.78%
CHEMBL2535	P11166	Glucose transporter	83.39%	98.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.57%	92.94%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.96%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.65%	96.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	80.47%	90.24%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.05%	93.40%

Plants that contains it

• Bocconia frutescens
• Chelidonium majus
• Glaucium flavum
• Macleaya microcarpa
• Stylophorum diphyllum

Cross-Links

• PubChem: 162918177
• LOTUS: LTS0136383
• wikiData: Q105226199