1,3,6-Trihydroxy-8-methylanthraquinone

Details

• Internal ID: ba0c6f23-d620-4826-aa9e-cd5dcfd3b1a9
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: 1,3,6-trihydroxy-8-methylanthracene-9,10-dione
• SMILES (Canonical): CC1=CC(=CC2=C1C(=O)C3=C(C2=O)C=C(C=C3O)O)O
• SMILES (Isomeric): CC1=CC(=CC2=C1C(=O)C3=C(C2=O)C=C(C=C3O)O)O
• InChI: InChI=1S/C15H10O5/c1-6-2-7(16)3-9-12(6)15(20)13-10(14(9)19)4-8(17)5-11(13)18/h2-5,16-18H,1H3
• InChI Key: YEQCMRHFAWAOKU-UHFFFAOYSA-N
• Popularity: 18 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: 2.70
• Atomic LogP (AlogP): 1.89
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

• 18499-83-7
• Deoxyerythrolaccin
• desoxyerythrolaccin
• SCHEMBL17867367
• DTXSID40487210
• 1,3,6-trihydroxy-8-methylanthracene-9,10-dione
• 1,3,6-trihydroxy-8-methyl-anthracene-9,10-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9856	98.56%
Caco-2	+	0.6384	63.84%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8053	80.53%
OATP2B1 inhibitior	-	0.7042	70.42%
OATP1B1 inhibitior	+	0.9515	95.15%
OATP1B3 inhibitior	+	0.9406	94.06%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.8850	88.50%
P-glycoprotein inhibitior	-	0.9320	93.20%
P-glycoprotein substrate	-	0.9779	97.79%
CYP3A4 substrate	-	0.5974	59.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8285	82.85%
CYP3A4 inhibition	-	0.5424	54.24%
CYP2C9 inhibition	+	0.8825	88.25%
CYP2C19 inhibition	-	0.5367	53.67%
CYP2D6 inhibition	-	0.6118	61.18%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.8726	87.26%
CYP inhibitory promiscuity	-	0.6156	61.56%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8096	80.96%
Carcinogenicity (trinary)	Non-required	0.6367	63.67%
Eye corrosion	-	0.9905	99.05%
Eye irritation	+	0.9726	97.26%
Skin irritation	+	0.6361	63.61%
Skin corrosion	-	0.8499	84.99%
Ames mutagenesis	+	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7698	76.98%
Micronuclear	+	0.7700	77.00%
Hepatotoxicity	+	0.7930	79.30%
skin sensitisation	-	0.8137	81.37%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	-	0.6667	66.67%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.7064	70.64%
Acute Oral Toxicity (c)	III	0.6654	66.54%
Estrogen receptor binding	+	0.6876	68.76%
Androgen receptor binding	+	0.5228	52.28%
Thyroid receptor binding	-	0.7492	74.92%
Glucocorticoid receptor binding	+	0.8385	83.85%
Aromatase binding	-	0.5552	55.52%
PPAR gamma	-	0.4862	48.62%
Honey bee toxicity	-	0.9444	94.44%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9742	97.42%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.97%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.62%	98.95%
CHEMBL1929	P47989	Xanthine dehydrogenase	92.85%	96.12%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.24%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.50%	89.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.05%	99.15%
CHEMBL4208	P20618	Proteasome component C5	90.77%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.55%	99.23%
CHEMBL1951	P21397	Monoamine oxidase A	88.49%	91.49%
CHEMBL3401	O75469	Pregnane X receptor	87.87%	94.73%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.54%	93.40%

Plants that contains it

• Aloe ferox
• Aloe maculata
• Asphodelus fistulosus
• Eleutherine bulbosa
• Gladiolus italicus
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum

Cross-Links

• PubChem: 12309204
• NPASS: NPC129815
• LOTUS: LTS0093516
• wikiData: Q82329154