(1R)-4,9-dihydroxy-10-methoxy-1-phenyl-1H-naphtho[3,2-e][2]benzofuran-3,6,11-trione

Details

• Internal ID: 900edb10-8e20-4203-a925-defb96bdf58b
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: (1R)-4,9-dihydroxy-10-methoxy-1-phenyl-1H-naphtho[3,2-e][2]benzofuran-3,6,11-trione
• SMILES (Canonical): COC1=C(C=CC2=C1C(=O)C3=C4C(OC(=O)C4=C(C=C3C2=O)O)C5=CC=CC=C5)O
• SMILES (Isomeric): COC1=C(C=CC2=C1C(=O)C3=C4[C@H](OC(=O)C4=C(C=C3C2=O)O)C5=CC=CC=C5)O
• InChI: InChI=1S/C23H14O7/c1-29-22-13(24)8-7-11-16(22)20(27)15-12(19(11)26)9-14(25)17-18(15)21(30-23(17)28)10-5-3-2-4-6-10/h2-9,21,24-25H,1H3/t21-/m1/s1
• InChI Key: XHIVQYWGRAIKSE-OAQYLSRUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₁₄O₇
• Molecular Weight: 402.40 g/mol
• Exact Mass: 402.07395278 g/mol
• Topological Polar Surface Area (TPSA): 110.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.14
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9830	98.30%
Caco-2	-	0.6132	61.32%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7972	79.72%
OATP2B1 inhibitior	-	0.7171	71.71%
OATP1B1 inhibitior	+	0.8829	88.29%
OATP1B3 inhibitior	+	0.9196	91.96%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6806	68.06%
P-glycoprotein inhibitior	-	0.4568	45.68%
P-glycoprotein substrate	-	0.8846	88.46%
CYP3A4 substrate	+	0.5524	55.24%
CYP2C9 substrate	-	0.5875	58.75%
CYP2D6 substrate	-	0.8363	83.63%
CYP3A4 inhibition	-	0.8476	84.76%
CYP2C9 inhibition	+	0.9196	91.96%
CYP2C19 inhibition	-	0.5146	51.46%
CYP2D6 inhibition	-	0.9003	90.03%
CYP1A2 inhibition	+	0.5906	59.06%
CYP2C8 inhibition	+	0.4867	48.67%
CYP inhibitory promiscuity	+	0.5616	56.16%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9343	93.43%
Carcinogenicity (trinary)	Warning	0.3642	36.42%
Eye corrosion	-	0.9868	98.68%
Eye irritation	+	0.5241	52.41%
Skin irritation	-	0.7015	70.15%
Skin corrosion	-	0.9559	95.59%
Ames mutagenesis	+	0.7192	71.92%
Human Ether-a-go-go-Related Gene inhibition	-	0.5458	54.58%
Micronuclear	+	0.9100	91.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.9281	92.81%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5279	52.79%
Acute Oral Toxicity (c)	III	0.5678	56.78%
Estrogen receptor binding	+	0.7855	78.55%
Androgen receptor binding	+	0.7246	72.46%
Thyroid receptor binding	-	0.6328	63.28%
Glucocorticoid receptor binding	+	0.6540	65.40%
Aromatase binding	-	0.7763	77.63%
PPAR gamma	+	0.5635	56.35%
Honey bee toxicity	-	0.8690	86.90%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9795	97.95%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.68%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.77%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.73%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.14%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	91.92%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.52%	86.33%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	90.02%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.61%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.23%	96.09%
CHEMBL2535	P11166	Glucose transporter	80.54%	98.75%
CHEMBL2056	P21728	Dopamine D1 receptor	80.00%	91.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 101644032
• LOTUS: LTS0000524
• wikiData: Q105328119