Dichotomine C

Details

• Internal ID: fceec1dd-daaf-4a01-ad05-22f8b7ceb2b3
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: methyl 1-[(1R)-1,2-dihydroxyethyl]-9H-pyrido[3,4-b]indole-3-carboxylate
• SMILES (Canonical): COC(=O)C1=NC(=C2C(=C1)C3=CC=CC=C3N2)C(CO)O
• SMILES (Isomeric): COC(=O)C1=NC(=C2C(=C1)C3=CC=CC=C3N2)[C@H](CO)O
• InChI: InChI=1S/C15H14N2O4/c1-21-15(20)11-6-9-8-4-2-3-5-10(8)16-13(9)14(17-11)12(19)7-18/h2-6,12,16,18-19H,7H2,1H3/t12-/m0/s1
• InChI Key: WKUVQUIYZHZZFT-LBPRGKRZSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄N₂O₄
• Molecular Weight: 286.28 g/mol
• Exact Mass: 286.09535693 g/mol
• Topological Polar Surface Area (TPSA): 95.40 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): 1.53
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• CHEMBL458036
• methyl 1-[(1R)-1,2-dihydroxyethyl]-9H-pyrido[3,4-b]indole-3-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7561	75.61%
Caco-2	+	0.5559	55.59%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5997	59.97%
OATP2B1 inhibitior	-	0.8549	85.49%
OATP1B1 inhibitior	+	0.8862	88.62%
OATP1B3 inhibitior	+	0.9416	94.16%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.5660	56.60%
P-glycoprotein inhibitior	-	0.8629	86.29%
P-glycoprotein substrate	-	0.7763	77.63%
CYP3A4 substrate	+	0.5749	57.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8223	82.23%
CYP3A4 inhibition	-	0.8418	84.18%
CYP2C9 inhibition	-	0.7474	74.74%
CYP2C19 inhibition	-	0.8461	84.61%
CYP2D6 inhibition	-	0.8554	85.54%
CYP1A2 inhibition	-	0.5111	51.11%
CYP2C8 inhibition	+	0.5467	54.67%
CYP inhibitory promiscuity	-	0.5789	57.89%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6833	68.33%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.8946	89.46%
Skin irritation	-	0.8159	81.59%
Skin corrosion	-	0.9484	94.84%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4911	49.11%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	-	0.6548	65.48%
skin sensitisation	-	0.8878	88.78%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.8389	83.89%
Acute Oral Toxicity (c)	III	0.6783	67.83%
Estrogen receptor binding	+	0.7925	79.25%
Androgen receptor binding	+	0.5783	57.83%
Thyroid receptor binding	+	0.6349	63.49%
Glucocorticoid receptor binding	+	0.8767	87.67%
Aromatase binding	+	0.7309	73.09%
PPAR gamma	+	0.5527	55.27%
Honey bee toxicity	-	0.9380	93.80%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.7251	72.51%
Fish aquatic toxicity	-	0.9178	91.78%

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	97.86%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.40%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.52%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.72%	94.45%
CHEMBL2581	P07339	Cathepsin D	91.48%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.70%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.43%	94.00%
CHEMBL2535	P11166	Glucose transporter	87.35%	98.75%
CHEMBL1781	P11387	DNA topoisomerase I	87.03%	97.00%
CHEMBL3401	O75469	Pregnane X receptor	86.23%	94.73%
CHEMBL2885	P07451	Carbonic anhydrase III	85.21%	87.45%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.24%	96.00%
CHEMBL255	P29275	Adenosine A2b receptor	83.11%	98.59%
CHEMBL213	P08588	Beta-1 adrenergic receptor	83.00%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.32%	96.95%

Plants that contains it

• Stellaria dichotoma

Cross-Links

• PubChem: 11254673
• NPASS: NPC89508
• ChEMBL: CHEMBL458036
• LOTUS: LTS0158762
• wikiData: Q105307723