Orellanine

Details

• Internal ID: bd564459-3dd3-4f0e-89ff-6619f0aa9cc9
• Taxonomy: Organoheterocyclic compounds > Pyridines and derivatives > Bipyridines and oligopyridines
• IUPAC Name: 2-(1,3-dihydroxy-4-oxo-2-pyridinyl)-1,3-dihydroxypyridin-4-one
• InChI: InChI=1S/C10H8N2O6/c13-5-1-3-11(17)7(9(5)15)8-10(16)6(14)2-4-12(8)18/h1-4,15-18H
• InChI Key: JGRNMEQUBVRSQR-UHFFFAOYSA-N
• Popularity: 64 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₈N₂O₆
• Molecular Weight: 252.18 g/mol
• Exact Mass: 252.03823598 g/mol
• Topological Polar Surface Area (TPSA): 122.00 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -0.44
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

• 37338-80-0
• (2,2'-Bipyridine)-3,3',4,4'-tetrol, 1,1'-dioxide
• 2-(1,3-dihydroxy-4-oxopyridin-2-yl)-1,3-dihydroxypyridin-4-one
• [2,2'-Bipyridine]-3,3',4,4'-tetrol, 1,1'-dioxide
• ORELLANINE [HSDB]
• SCHEMBL388071
• 082U1GSX3D
• [2,2'-Bipyridine]-3,3',4,4'-tetrol,1,1'-dioxide
• CHEMBL2152646
• CHEBI:190273
• HY-W661499
• CS-0745189
• Q420527
• 3,3',4,4'-tetrahydroxy-2,2'-bipyridyl-N,N'-dioxide
• 3,3',4,4'-TETRAHYDROXY-2,2'-BIPYRIDINE-1,1'-DIOXIDE
• 2-(3,4-Dihydroxy-1-oxidopyridin-1-ium-2-yl)-3,4-dihydroxypyridin-1-ium-1-olate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8292	82.92%
Caco-2	-	0.7590	75.90%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7595	75.95%
OATP2B1 inhibitior	-	0.8532	85.32%
OATP1B1 inhibitior	+	0.9444	94.44%
OATP1B3 inhibitior	+	0.9303	93.03%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8812	88.12%
P-glycoprotein inhibitior	-	0.9451	94.51%
P-glycoprotein substrate	-	0.9897	98.97%
CYP3A4 substrate	-	0.7507	75.07%
CYP2C9 substrate	-	0.7622	76.22%
CYP2D6 substrate	-	0.8719	87.19%
CYP3A4 inhibition	-	0.8223	82.23%
CYP2C9 inhibition	-	0.6441	64.41%
CYP2C19 inhibition	-	0.8169	81.69%
CYP2D6 inhibition	-	0.8891	88.91%
CYP1A2 inhibition	-	0.6524	65.24%
CYP2C8 inhibition	-	0.9799	97.99%
CYP inhibitory promiscuity	-	0.7438	74.38%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.8213	82.13%
Carcinogenicity (trinary)	Non-required	0.5556	55.56%
Eye corrosion	-	0.9836	98.36%
Eye irritation	-	0.5000	50.00%
Skin irritation	-	0.7605	76.05%
Skin corrosion	-	0.9327	93.27%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8966	89.66%
Micronuclear	+	0.8600	86.00%
Hepatotoxicity	+	0.7551	75.51%
skin sensitisation	-	0.8517	85.17%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6767	67.67%
Acute Oral Toxicity (c)	III	0.6199	61.99%
Estrogen receptor binding	+	0.6396	63.96%
Androgen receptor binding	-	0.5372	53.72%
Thyroid receptor binding	-	0.5255	52.55%
Glucocorticoid receptor binding	+	0.9445	94.45%
Aromatase binding	+	0.5233	52.33%
PPAR gamma	+	0.5691	56.91%
Honey bee toxicity	-	0.9461	94.61%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.6998	69.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	92.02%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.55%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	84.38%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.08%	95.56%
CHEMBL4208	P20618	Proteasome component C5	83.42%	90.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 89579
• LOTUS: LTS0059267
• wikiData: Q420527