dichotomine B

Details

• Internal ID: a2852a74-9437-4fd9-8696-47e50581c06d
• Taxonomy: Alkaloids and derivatives > Harmala alkaloids
• IUPAC Name: 1-[(1R)-1,2-dihydroxyethyl]-9H-pyrido[3,4-b]indole-3-carboxylic acid
• SMILES (Canonical): C1=CC=C2C(=C1)C3=CC(=NC(=C3N2)C(CO)O)C(=O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C3=CC(=NC(=C3N2)[C@H](CO)O)C(=O)O
• InChI: InChI=1S/C14H12N2O4/c17-6-11(18)13-12-8(5-10(16-13)14(19)20)7-3-1-2-4-9(7)15-12/h1-5,11,15,17-18H,6H2,(H,19,20)/t11-/m0/s1
• InChI Key: PKSXEHHRROSXPR-NSHDSACASA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂N₂O₄
• Molecular Weight: 272.26 g/mol
• Exact Mass: 272.07970687 g/mol
• Topological Polar Surface Area (TPSA): 106.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 1.44
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 755036-41-0
• CHEMBL457820
• HY-N10386
• AKOS040763525
• MS-23853
• CS-0498890
• E83703

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7949	79.49%
Caco-2	-	0.8441	84.41%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5828	58.28%
OATP2B1 inhibitior	-	0.8582	85.82%
OATP1B1 inhibitior	+	0.9127	91.27%
OATP1B3 inhibitior	+	0.9376	93.76%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6590	65.90%
P-glycoprotein inhibitior	-	0.9306	93.06%
P-glycoprotein substrate	-	0.9039	90.39%
CYP3A4 substrate	-	0.5545	55.45%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8597	85.97%
CYP3A4 inhibition	-	0.8998	89.98%
CYP2C9 inhibition	-	0.8224	82.24%
CYP2C19 inhibition	-	0.9201	92.01%
CYP2D6 inhibition	-	0.8629	86.29%
CYP1A2 inhibition	-	0.6042	60.42%
CYP2C8 inhibition	-	0.6193	61.93%
CYP inhibitory promiscuity	-	0.8015	80.15%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7272	72.72%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.5166	51.66%
Skin irritation	-	0.7970	79.70%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.6023	60.23%
Human Ether-a-go-go-Related Gene inhibition	-	0.7537	75.37%
Micronuclear	+	0.7100	71.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8832	88.32%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.8628	86.28%
Acute Oral Toxicity (c)	III	0.6348	63.48%
Estrogen receptor binding	+	0.6916	69.16%
Androgen receptor binding	+	0.6275	62.75%
Thyroid receptor binding	+	0.5470	54.70%
Glucocorticoid receptor binding	+	0.8066	80.66%
Aromatase binding	+	0.7246	72.46%
PPAR gamma	+	0.7484	74.84%
Honey bee toxicity	-	0.9475	94.75%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7651	76.51%
Fish aquatic toxicity	-	0.8807	88.07%

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	94.37%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	93.81%	94.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.74%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.62%	98.95%
CHEMBL1781	P11387	DNA topoisomerase I	89.39%	97.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.74%	95.56%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	87.34%	89.44%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.58%	99.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.63%	85.14%
CHEMBL213	P08588	Beta-1 adrenergic receptor	85.41%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.33%	94.45%
CHEMBL3902	P09211	Glutathione S-transferase Pi	84.46%	93.81%
CHEMBL1811	P34995	Prostanoid EP1 receptor	81.57%	95.71%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	80.19%	91.71%

Plants that contains it

• Stellaria dichotoma

Cross-Links

• PubChem: 11173314
• NPASS: NPC244741
• LOTUS: LTS0173179
• wikiData: Q105210628