5,8-Dihydroxy-3-(hydroxymethyl)benzo[f][2]benzofuran-4,9-dione

Details

• Internal ID: 1e931baf-d98c-475e-8134-18a9bcfddfb3
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: 5,8-dihydroxy-3-(hydroxymethyl)benzo[f][2]benzofuran-4,9-dione
• SMILES (Canonical): C1=CC(=C2C(=C1O)C(=O)C3=COC(=C3C2=O)CO)O
• SMILES (Isomeric): C1=CC(=C2C(=C1O)C(=O)C3=COC(=C3C2=O)CO)O
• InChI: InChI=1S/C13H8O6/c14-3-8-9-5(4-19-8)12(17)10-6(15)1-2-7(16)11(10)13(9)18/h1-2,4,14-16H,3H2
• InChI Key: VTNVITVPYSHXGH-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₈O₆
• Molecular Weight: 260.20 g/mol
• Exact Mass: 260.03208797 g/mol
• Topological Polar Surface Area (TPSA): 108.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 0.96
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9857	98.57%
Caco-2	-	0.8311	83.11%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7544	75.44%
OATP2B1 inhibitior	-	0.6941	69.41%
OATP1B1 inhibitior	+	0.9374	93.74%
OATP1B3 inhibitior	+	0.9033	90.33%
MATE1 inhibitior	-	0.5600	56.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9256	92.56%
P-glycoprotein inhibitior	-	0.9607	96.07%
P-glycoprotein substrate	-	0.9737	97.37%
CYP3A4 substrate	-	0.6494	64.94%
CYP2C9 substrate	-	0.6257	62.57%
CYP2D6 substrate	-	0.8403	84.03%
CYP3A4 inhibition	-	0.9167	91.67%
CYP2C9 inhibition	+	0.6689	66.89%
CYP2C19 inhibition	-	0.5863	58.63%
CYP2D6 inhibition	-	0.9130	91.30%
CYP1A2 inhibition	+	0.7350	73.50%
CYP2C8 inhibition	-	0.8952	89.52%
CYP inhibitory promiscuity	-	0.5165	51.65%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9243	92.43%
Carcinogenicity (trinary)	Non-required	0.5166	51.66%
Eye corrosion	-	0.9850	98.50%
Eye irritation	+	0.9257	92.57%
Skin irritation	-	0.7122	71.22%
Skin corrosion	-	0.9596	95.96%
Ames mutagenesis	+	0.8700	87.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.9249	92.49%
Micronuclear	+	0.6418	64.18%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.7507	75.07%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.6882	68.82%
Acute Oral Toxicity (c)	II	0.5444	54.44%
Estrogen receptor binding	-	0.6047	60.47%
Androgen receptor binding	+	0.6960	69.60%
Thyroid receptor binding	-	0.7682	76.82%
Glucocorticoid receptor binding	+	0.7630	76.30%
Aromatase binding	+	0.5346	53.46%
PPAR gamma	+	0.8265	82.65%
Honey bee toxicity	-	0.9267	92.67%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.8191	81.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.87%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.30%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.63%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	87.72%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.65%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.40%	99.15%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.21%	86.92%
CHEMBL3004	P33527	Multidrug resistance-associated protein 1	81.00%	96.37%

Plants that contains it

• Bulbine capitata
• Bulbine frutescens

Cross-Links

• PubChem: 135453894
• LOTUS: LTS0009436
• wikiData: Q105292897