1,3,8-Trihydroxy-6-propyl-9,10-anthraquinone

Details

• Internal ID: ac4eef14-e94e-4c3c-8e5f-8786b4d9f804
• Taxonomy: Benzenoids > Anthracenes > Anthraquinones > Hydroxyanthraquinones
• IUPAC Name: 1,3,8-trihydroxy-6-propylanthracene-9,10-dione
• SMILES (Canonical): CCCC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)O
• SMILES (Isomeric): CCCC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=C(C=C3O)O
• InChI: InChI=1S/C17H14O5/c1-2-3-8-4-10-14(12(19)5-8)17(22)15-11(16(10)21)6-9(18)7-13(15)20/h4-7,18-20H,2-3H2,1H3
• InChI Key: XJZIVQGVSOVEOC-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₄O₅
• Molecular Weight: 298.29 g/mol
• Exact Mass: 298.08412354 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 2.53
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9531	95.31%
Caco-2	+	0.5482	54.82%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8044	80.44%
OATP2B1 inhibitior	-	0.5657	56.57%
OATP1B1 inhibitior	+	0.9019	90.19%
OATP1B3 inhibitior	+	0.9602	96.02%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9331	93.31%
P-glycoprotein inhibitior	-	0.9268	92.68%
P-glycoprotein substrate	-	0.8802	88.02%
CYP3A4 substrate	-	0.5473	54.73%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7875	78.75%
CYP3A4 inhibition	-	0.5598	55.98%
CYP2C9 inhibition	+	0.7268	72.68%
CYP2C19 inhibition	+	0.5072	50.72%
CYP2D6 inhibition	-	0.6624	66.24%
CYP1A2 inhibition	+	0.8449	84.49%
CYP2C8 inhibition	-	0.7079	70.79%
CYP inhibitory promiscuity	+	0.5774	57.74%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8465	84.65%
Carcinogenicity (trinary)	Non-required	0.6275	62.75%
Eye corrosion	-	0.9865	98.65%
Eye irritation	+	0.8228	82.28%
Skin irritation	-	0.6164	61.64%
Skin corrosion	-	0.7965	79.65%
Ames mutagenesis	+	0.6946	69.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.6395	63.95%
Micronuclear	-	0.5941	59.41%
Hepatotoxicity	+	0.6085	60.85%
skin sensitisation	-	0.8258	82.58%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.7078	70.78%
Acute Oral Toxicity (c)	III	0.6799	67.99%
Estrogen receptor binding	+	0.6951	69.51%
Androgen receptor binding	+	0.6239	62.39%
Thyroid receptor binding	-	0.6794	67.94%
Glucocorticoid receptor binding	+	0.8739	87.39%
Aromatase binding	+	0.5900	59.00%
PPAR gamma	+	0.9086	90.86%
Honey bee toxicity	-	0.9431	94.31%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5032	50.32%
Fish aquatic toxicity	+	0.9869	98.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.92%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.38%	96.09%
CHEMBL1929	P47989	Xanthine dehydrogenase	90.28%	96.12%
CHEMBL4208	P20618	Proteasome component C5	89.18%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.08%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.88%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	87.61%	95.93%
CHEMBL3401	O75469	Pregnane X receptor	87.37%	94.73%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.15%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.54%	96.95%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	83.56%	92.68%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.34%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.63%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.45%	99.17%
CHEMBL255	P29275	Adenosine A2b receptor	80.12%	98.59%

Plants that contains it

• Fraxinus ornus
• Prunus mume

Cross-Links

• PubChem: 23265983
• NPASS: NPC284372
• LOTUS: LTS0150560
• wikiData: Q105329351