1,5-Dihydroxy-3-(hydroxymethyl)anthracene-9,10-dione

Details

• Internal ID: 974b54f7-80be-47ab-9240-fab499635206
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 1,5-dihydroxy-3-(hydroxymethyl)anthracene-9,10-dione
• SMILES (Canonical): C1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C(=CC(=C3)CO)O
• SMILES (Isomeric): C1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C(=CC(=C3)CO)O
• InChI: InChI=1S/C15H10O5/c16-6-7-4-9-13(11(18)5-7)14(19)8-2-1-3-10(17)12(8)15(9)20/h1-5,16-18H,6H2
• InChI Key: WPKQIGIVDUYIBC-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₀O₅
• Molecular Weight: 270.24 g/mol
• Exact Mass: 270.05282342 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.37
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• 1,5-dihydroxy-3-(hydroxymethyl)anthracene-9,10-dione
• 1,5-Dihydroxy-3-hydroxymethyl-9,10-anthraquinone
• 1,5-dihydroxy-3-hydroxymethylanthraquinone
• CHEMBL2229890
• 9,10-Anthracenedione, 1,5-dihydroxy-3-(hydroxymethyl)-
• DTXSID20347101
• WPKQIGIVDUYIBC-UHFFFAOYSA-N
• 1,5-Dihydroxy-3-(hydroxymethyl)anthra-9,10-quinone #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9784	97.84%
Caco-2	-	0.8465	84.65%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8344	83.44%
OATP2B1 inhibitior	-	0.6900	69.00%
OATP1B1 inhibitior	+	0.8967	89.67%
OATP1B3 inhibitior	+	0.9464	94.64%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7503	75.03%
P-glycoprotein inhibitior	-	0.9244	92.44%
P-glycoprotein substrate	-	0.9300	93.00%
CYP3A4 substrate	-	0.5839	58.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8175	81.75%
CYP3A4 inhibition	-	0.7395	73.95%
CYP2C9 inhibition	+	0.6696	66.96%
CYP2C19 inhibition	-	0.5000	50.00%
CYP2D6 inhibition	-	0.7660	76.60%
CYP1A2 inhibition	+	0.7957	79.57%
CYP2C8 inhibition	-	0.8914	89.14%
CYP inhibitory promiscuity	-	0.5708	57.08%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7787	77.87%
Carcinogenicity (trinary)	Non-required	0.5990	59.90%
Eye corrosion	-	0.9915	99.15%
Eye irritation	+	0.9717	97.17%
Skin irritation	-	0.5719	57.19%
Skin corrosion	-	0.9731	97.31%
Ames mutagenesis	+	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8627	86.27%
Micronuclear	+	0.5859	58.59%
Hepatotoxicity	+	0.5677	56.77%
skin sensitisation	-	0.8314	83.14%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.6401	64.01%
Acute Oral Toxicity (c)	II	0.4555	45.55%
Estrogen receptor binding	+	0.7808	78.08%
Androgen receptor binding	+	0.6055	60.55%
Thyroid receptor binding	-	0.6988	69.88%
Glucocorticoid receptor binding	+	0.9019	90.19%
Aromatase binding	+	0.7018	70.18%
PPAR gamma	+	0.8680	86.80%
Honey bee toxicity	-	0.9301	93.01%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9576	95.76%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.47%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.09%	95.56%
CHEMBL1951	P21397	Monoamine oxidase A	94.01%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.07%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	90.69%	95.93%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.97%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	88.06%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.39%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.65%	96.09%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	83.47%	96.67%
CHEMBL2535	P11166	Glucose transporter	82.83%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.14%	94.00%

Plants that contains it

• Aloe excelsa

Cross-Links

• PubChem: 617886
• LOTUS: LTS0154171
• wikiData: Q82120676