1,8-Dihydroxy-2-(hydroxymethyl)-5-methoxyanthraquinone

Details

• Internal ID: b6176852-4811-45b0-8aa3-ff2110467aee
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones
• IUPAC Name: 1,8-dihydroxy-2-(hydroxymethyl)-5-methoxyanthracene-9,10-dione
• SMILES (Canonical): COC1=C2C(=C(C=C1)O)C(=O)C3=C(C2=O)C=CC(=C3O)CO
• SMILES (Isomeric): COC1=C2C(=C(C=C1)O)C(=O)C3=C(C2=O)C=CC(=C3O)CO
• InChI: InChI=1S/C16H12O6/c1-22-10-5-4-9(18)12-13(10)15(20)8-3-2-7(6-17)14(19)11(8)16(12)21/h2-5,17-19H,6H2,1H3
• InChI Key: KCRYZHDWIWWELK-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₂O₆
• Molecular Weight: 300.26 g/mol
• Exact Mass: 300.06338810 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.37
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• SCHEMBL16227013
• 1,8-Dihydroxy-2-(hydroxymethyl)-5-methoxyanthraquinone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9804	98.04%
Caco-2	-	0.5842	58.42%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	+	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7735	77.35%
OATP2B1 inhibitior	-	0.5717	57.17%
OATP1B1 inhibitior	+	0.9312	93.12%
OATP1B3 inhibitior	+	0.9292	92.92%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6677	66.77%
P-glycoprotein inhibitior	-	0.8686	86.86%
P-glycoprotein substrate	-	0.7920	79.20%
CYP3A4 substrate	+	0.5197	51.97%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7944	79.44%
CYP3A4 inhibition	-	0.8029	80.29%
CYP2C9 inhibition	-	0.5476	54.76%
CYP2C19 inhibition	-	0.5386	53.86%
CYP2D6 inhibition	-	0.9054	90.54%
CYP1A2 inhibition	+	0.8473	84.73%
CYP2C8 inhibition	-	0.6486	64.86%
CYP inhibitory promiscuity	-	0.5398	53.98%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8385	83.85%
Carcinogenicity (trinary)	Non-required	0.7138	71.38%
Eye corrosion	-	0.9877	98.77%
Eye irritation	+	0.7755	77.55%
Skin irritation	-	0.7351	73.51%
Skin corrosion	-	0.9445	94.45%
Ames mutagenesis	+	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6996	69.96%
Micronuclear	+	0.5959	59.59%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8685	86.85%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.5778	57.78%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.5857	58.57%
Acute Oral Toxicity (c)	III	0.6284	62.84%
Estrogen receptor binding	+	0.9565	95.65%
Androgen receptor binding	+	0.7083	70.83%
Thyroid receptor binding	-	0.6189	61.89%
Glucocorticoid receptor binding	+	0.9383	93.83%
Aromatase binding	+	0.8083	80.83%
PPAR gamma	+	0.7688	76.88%
Honey bee toxicity	-	0.8845	88.45%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6749	67.49%
Fish aquatic toxicity	+	0.9461	94.61%

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	97.83%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.19%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.31%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.45%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.46%	94.00%
CHEMBL4208	P20618	Proteasome component C5	88.14%	90.00%
CHEMBL1255126	O15151	Protein Mdm4	87.45%	90.20%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.35%	89.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	85.39%	96.67%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.30%	96.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.26%	99.15%
CHEMBL3194	P02766	Transthyretin	81.86%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.00%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	80.60%	94.73%
CHEMBL2535	P11166	Glucose transporter	80.26%	98.75%

Plants that contains it

• Morinda citrifolia

Cross-Links

• PubChem: 14189688
• NPASS: NPC300540
• LOTUS: LTS0237077
• wikiData: Q105138910