1,5,15-Tri-O-methylmorindol

Details

• Internal ID: 8a87ca88-b126-4c4b-a1a5-0eb4b82cb2a9
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: 2-hydroxy-1,5-dimethoxy-6-(methoxymethyl)anthracene-9,10-dione
• SMILES (Canonical): COCC1=C(C2=C(C=C1)C(=O)C3=C(C2=O)C=CC(=C3OC)O)OC
• SMILES (Isomeric): COCC1=C(C2=C(C=C1)C(=O)C3=C(C2=O)C=CC(=C3OC)O)OC
• InChI: InChI=1S/C18H16O6/c1-22-8-9-4-5-10-13(17(9)23-2)15(20)11-6-7-12(19)18(24-3)14(11)16(10)21/h4-7,19H,8H2,1-3H3
• InChI Key: HEVJQUHAJKODII-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₆O₆
• Molecular Weight: 328.30 g/mol
• Exact Mass: 328.09468823 g/mol
• Topological Polar Surface Area (TPSA): 82.10 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.33
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• 942609-65-6
• 2-HYDROXY-1,5-DIMETHOXY-6-(METHOXYMETHYL)ANTHRACENE-9,10-DIONE
• 9,10-Anthracenedione, 2-hydroxy-1,5-dimethoxy-6-(methoxymethyl)-
• 1,5,15-Trimethylmorindol
• CHEMBL227461
• HEVJQUHAJKODII-UHFFFAOYSA-N
• 2-hydroxy-1,5-dimethoxy-6-(methoxymethyl)-9,10-anthraquinone
• AKOS032961775
• B0005-190261

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9890	98.90%
Caco-2	+	0.7970	79.70%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8170	81.70%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9354	93.54%
OATP1B3 inhibitior	+	0.8645	86.45%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6036	60.36%
P-glycoprotein inhibitior	-	0.7070	70.70%
P-glycoprotein substrate	-	0.9186	91.86%
CYP3A4 substrate	-	0.5285	52.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7079	70.79%
CYP3A4 inhibition	-	0.7930	79.30%
CYP2C9 inhibition	-	0.5929	59.29%
CYP2C19 inhibition	-	0.6611	66.11%
CYP2D6 inhibition	-	0.8822	88.22%
CYP1A2 inhibition	+	0.8105	81.05%
CYP2C8 inhibition	-	0.7495	74.95%
CYP inhibitory promiscuity	-	0.7535	75.35%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8963	89.63%
Carcinogenicity (trinary)	Non-required	0.6044	60.44%
Eye corrosion	-	0.9878	98.78%
Eye irritation	+	0.6801	68.01%
Skin irritation	-	0.8539	85.39%
Skin corrosion	-	0.9762	97.62%
Ames mutagenesis	+	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7648	76.48%
Micronuclear	+	0.5359	53.59%
Hepatotoxicity	+	0.5302	53.02%
skin sensitisation	-	0.7819	78.19%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.6327	63.27%
Acute Oral Toxicity (c)	III	0.5531	55.31%
Estrogen receptor binding	+	0.8705	87.05%
Androgen receptor binding	+	0.5500	55.00%
Thyroid receptor binding	-	0.5333	53.33%
Glucocorticoid receptor binding	+	0.8336	83.36%
Aromatase binding	+	0.6878	68.78%
PPAR gamma	+	0.7369	73.69%
Honey bee toxicity	-	0.8903	89.03%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.9800	98.00%

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	97.06%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.25%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.57%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.52%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.91%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.46%	86.33%
CHEMBL4208	P20618	Proteasome component C5	84.30%	90.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.83%	80.78%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	83.77%	96.67%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.94%	94.00%

Plants that contains it

• Morinda citrifolia

Cross-Links

• PubChem: 16203753
• NPASS: NPC164912
• LOTUS: LTS0152063
• wikiData: Q105027064