5,7-dihydroxy-4-(hydroxymethyl)-10-methoxy-1H-naphtho[3,2-e][2]benzofuran-3,6,11-trione

Details

• Internal ID: 7480c126-3698-4f61-a789-1e241eaccace
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 5,7-dihydroxy-4-(hydroxymethyl)-10-methoxy-1H-naphtho[3,2-e][2]benzofuran-3,6,11-trione
• SMILES (Canonical): COC1=C2C(=C(C=C1)O)C(=O)C3=C(C2=O)C4=C(C(=C3O)CO)C(=O)OC4
• SMILES (Isomeric): COC1=C2C(=C(C=C1)O)C(=O)C3=C(C2=O)C4=C(C(=C3O)CO)C(=O)OC4
• InChI: InChI=1S/C18H12O8/c1-25-9-3-2-8(20)12-13(9)16(22)11-7-5-26-18(24)10(7)6(4-19)15(21)14(11)17(12)23/h2-3,19-21H,4-5H2,1H3
• InChI Key: WVRRASZWZHBZJR-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₂O₈
• Molecular Weight: 356.30 g/mol
• Exact Mass: 356.05321734 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 1.04
• H-Bond Acceptor: 8
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9522	95.22%
Caco-2	+	0.5499	54.99%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7599	75.99%
OATP2B1 inhibitior	-	0.5670	56.70%
OATP1B1 inhibitior	+	0.9263	92.63%
OATP1B3 inhibitior	+	0.9455	94.55%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6483	64.83%
P-glycoprotein inhibitior	-	0.8540	85.40%
P-glycoprotein substrate	-	0.8008	80.08%
CYP3A4 substrate	+	0.5141	51.41%
CYP2C9 substrate	-	0.5905	59.05%
CYP2D6 substrate	-	0.8366	83.66%
CYP3A4 inhibition	-	0.8442	84.42%
CYP2C9 inhibition	+	0.5654	56.54%
CYP2C19 inhibition	-	0.5000	50.00%
CYP2D6 inhibition	-	0.9273	92.73%
CYP1A2 inhibition	-	0.5107	51.07%
CYP2C8 inhibition	-	0.7558	75.58%
CYP inhibitory promiscuity	+	0.5762	57.62%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9143	91.43%
Carcinogenicity (trinary)	Non-required	0.6374	63.74%
Eye corrosion	-	0.9861	98.61%
Eye irritation	+	0.6719	67.19%
Skin irritation	-	0.8268	82.68%
Skin corrosion	-	0.9586	95.86%
Ames mutagenesis	+	0.8900	89.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6876	68.76%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	+	0.6927	69.27%
skin sensitisation	-	0.8384	83.84%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.6280	62.80%
Estrogen receptor binding	+	0.8820	88.20%
Androgen receptor binding	+	0.7160	71.60%
Thyroid receptor binding	-	0.5882	58.82%
Glucocorticoid receptor binding	+	0.8385	83.85%
Aromatase binding	-	0.5221	52.21%
PPAR gamma	+	0.7920	79.20%
Honey bee toxicity	-	0.9102	91.02%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6749	67.49%
Fish aquatic toxicity	+	0.9675	96.75%

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	97.54%	91.11%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	97.30%	98.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.98%	95.56%
CHEMBL2581	P07339	Cathepsin D	92.99%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.96%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.75%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.21%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.04%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.31%	96.09%
CHEMBL4208	P20618	Proteasome component C5	85.99%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.12%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	81.92%	94.73%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.34%	93.99%

Plants that contains it

• Berchemia discolor

Cross-Links

• PubChem: 14704555
• LOTUS: LTS0100747
• wikiData: Q105313690