Methyl 12-(1-hydroxyethyl)-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,9,13-pentaene-10-carboxylate

Details

• Internal ID: 304066ea-4358-4197-965a-1cb53b5da63c
• Taxonomy: Alkaloids and derivatives > Plumeran-type alkaloids
• IUPAC Name: methyl 12-(1-hydroxyethyl)-5-methoxy-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,9,13-pentaene-10-carboxylate
• SMILES (Canonical): CC(C12CC(=C3C4(C1N(CC4)CC=C2)C5=C(N3)C=C(C=C5)OC)C(=O)OC)O
• SMILES (Isomeric): CC(C12CC(=C3C4(C1N(CC4)CC=C2)C5=C(N3)C=C(C=C5)OC)C(=O)OC)O
• InChI: InChI=1S/C22H26N2O4/c1-13(25)21-7-4-9-24-10-8-22(20(21)24)16-6-5-14(27-2)11-17(16)23-18(22)15(12-21)19(26)28-3/h4-7,11,13,20,23,25H,8-10,12H2,1-3H3
• InChI Key: ASAFZNAXYPDIJR-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₆N₂O₄
• Molecular Weight: 382.50 g/mol
• Exact Mass: 382.18925731 g/mol
• Topological Polar Surface Area (TPSA): 71.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 2.20
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 50656-92-3
• methyl (1R,12S,19R)-12-[(1R)-1-hydroxyethyl]-5-methoxy-8,16-diazapentacyclo[10.6.1.0^{1,9.0^{2,7.0^{16,19]nonadeca-2(7),3,5,9,13-pentaene-10-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9203	92.03%
Caco-2	+	0.7551	75.51%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7988	79.88%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.9031	90.31%
OATP1B3 inhibitior	+	0.9248	92.48%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9084	90.84%
P-glycoprotein inhibitior	-	0.5585	55.85%
P-glycoprotein substrate	+	0.7503	75.03%
CYP3A4 substrate	+	0.6805	68.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8096	80.96%
CYP3A4 inhibition	-	0.8483	84.83%
CYP2C9 inhibition	-	0.8080	80.80%
CYP2C19 inhibition	-	0.8592	85.92%
CYP2D6 inhibition	-	0.5616	56.16%
CYP1A2 inhibition	-	0.7206	72.06%
CYP2C8 inhibition	-	0.6822	68.22%
CYP inhibitory promiscuity	-	0.7687	76.87%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5457	54.57%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.9868	98.68%
Skin irritation	-	0.7592	75.92%
Skin corrosion	-	0.9317	93.17%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6723	67.23%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.5040	50.40%
skin sensitisation	-	0.8384	83.84%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.8380	83.80%
Acute Oral Toxicity (c)	III	0.5571	55.71%
Estrogen receptor binding	+	0.7209	72.09%
Androgen receptor binding	+	0.6758	67.58%
Thyroid receptor binding	+	0.6057	60.57%
Glucocorticoid receptor binding	+	0.8017	80.17%
Aromatase binding	+	0.7229	72.29%
PPAR gamma	+	0.6479	64.79%
Honey bee toxicity	-	0.8821	88.21%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9759	97.59%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.56%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.40%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.49%	91.11%
CHEMBL4208	P20618	Proteasome component C5	97.68%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.73%	94.45%
CHEMBL240	Q12809	HERG	96.28%	89.76%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	93.37%	91.03%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	91.57%	90.71%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	91.21%	91.07%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.70%	95.89%
CHEMBL2581	P07339	Cathepsin D	89.64%	98.95%
CHEMBL2535	P11166	Glucose transporter	88.26%	98.75%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	87.23%	93.03%
CHEMBL221	P23219	Cyclooxygenase-1	86.67%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.40%	95.56%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	85.18%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.06%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.54%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.21%	92.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.66%	99.15%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.54%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.69%	91.19%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.27%	94.00%

Plants that contains it

• Catharanthus roseus

Cross-Links

• PubChem: 73657393
• LOTUS: LTS0090234
• wikiData: Q104917703