(2S)-3alpha-Hydroxymethyl-3,4-dihydro-2beta-methyl-4alpha-[(9-methyl-9H-pyrido[3,4-b]indol-1-yl)methyl]-2H-pyran-5-carboxylic acid methyl ester

Details

• Internal ID: ca54ef26-5ad1-486f-838a-fbde1a43c5bf
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: methyl 3-(hydroxymethyl)-2-methyl-4-[(9-methylpyrido[3,4-b]indol-1-yl)methyl]-3,4-dihydro-2H-pyran-5-carboxylate
• InChI: InChI=1S/C22H24N2O4/c1-13-17(11-25)16(18(12-28-13)22(26)27-3)10-19-21-15(8-9-23-19)14-6-4-5-7-20(14)24(21)2/h4-9,12-13,16-17,25H,10-11H2,1-3H3
• InChI Key: ZHSWZGYEMVSUSM-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₄N₂O₄
• Molecular Weight: 380.40 g/mol
• Exact Mass: 380.17360725 g/mol
• Topological Polar Surface Area (TPSA): 73.60 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.97
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9192	91.92%
Caco-2	+	0.7420	74.20%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.4461	44.61%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8732	87.32%
OATP1B3 inhibitior	+	0.9302	93.02%
MATE1 inhibitior	-	0.7012	70.12%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.7028	70.28%
P-glycoprotein inhibitior	+	0.7175	71.75%
P-glycoprotein substrate	+	0.6702	67.02%
CYP3A4 substrate	+	0.6758	67.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8773	87.73%
CYP3A4 inhibition	-	0.5366	53.66%
CYP2C9 inhibition	-	0.7481	74.81%
CYP2C19 inhibition	-	0.6875	68.75%
CYP2D6 inhibition	-	0.7344	73.44%
CYP1A2 inhibition	-	0.5000	50.00%
CYP2C8 inhibition	+	0.7150	71.50%
CYP inhibitory promiscuity	+	0.7079	70.79%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5808	58.08%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9790	97.90%
Skin irritation	-	0.7809	78.09%
Skin corrosion	-	0.9408	94.08%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9327	93.27%
Micronuclear	+	0.6900	69.00%
Hepatotoxicity	+	0.7160	71.60%
skin sensitisation	-	0.8704	87.04%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	-	0.6778	67.78%
Acute Oral Toxicity (c)	III	0.6364	63.64%
Estrogen receptor binding	+	0.8316	83.16%
Androgen receptor binding	+	0.7205	72.05%
Thyroid receptor binding	+	0.7078	70.78%
Glucocorticoid receptor binding	+	0.7013	70.13%
Aromatase binding	+	0.5821	58.21%
PPAR gamma	-	0.5239	52.39%
Honey bee toxicity	-	0.8708	87.08%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6651	66.51%
Fish aquatic toxicity	+	0.9393	93.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.10%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.19%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	92.84%	94.73%
CHEMBL2581	P07339	Cathepsin D	92.14%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.08%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.03%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.07%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.90%	95.56%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	85.71%	88.00%
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	85.43%	96.47%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.36%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.14%	96.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.07%	95.83%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.83%	99.23%

Plants that contains it

• Alstonia constricta

Cross-Links

• PubChem: 12305772
• LOTUS: LTS0168932
• wikiData: Q105375981