4-hydroxy-9,10-dioxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(3-methoxy-3-oxopropanoyl)oxymethyl]oxan-2-yl]oxyanthracene-2-carboxylic acid

Details

• Internal ID: bcf00226-c7d6-47f1-a10a-3f32240bb373
• Taxonomy: Benzenoids > Anthracenes > Anthracenecarboxylic acids and derivatives > Anthracenecarboxylic acids
• IUPAC Name: 4-hydroxy-9,10-dioxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[(3-methoxy-3-oxopropanoyl)oxymethyl]oxan-2-yl]oxyanthracene-2-carboxylic acid
• SMILES (Canonical): COC(=O)CC(=O)OCC1C(C(C(C(O1)OC2=CC=CC3=C2C(=O)C4=C(C3=O)C=C(C=C4O)C(=O)O)O)O)O
• SMILES (Isomeric): COC(=O)CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=CC=CC3=C2C(=O)C4=C(C3=O)C=C(C=C4O)C(=O)O)O)O)O
• InChI: InChI=1S/C25H22O14/c1-36-15(27)7-16(28)37-8-14-20(30)22(32)23(33)25(39-14)38-13-4-2-3-10-18(13)21(31)17-11(19(10)29)5-9(24(34)35)6-12(17)26/h2-6,14,20,22-23,25-26,30,32-33H,7-8H2,1H3,(H,34,35)/t14-,20-,22+,23-,25-/m1/s1
• InChI Key: YSIHWESKGAFWRC-CTNIZGFHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₂O₁₄
• Molecular Weight: 546.40 g/mol
• Exact Mass: 546.10095537 g/mol
• Topological Polar Surface Area (TPSA): 223.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): -0.84
• H-Bond Acceptor: 13
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5946	59.46%
Caco-2	-	0.9106	91.06%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6049	60.49%
OATP2B1 inhibitior	-	0.8459	84.59%
OATP1B1 inhibitior	+	0.8937	89.37%
OATP1B3 inhibitior	+	0.9509	95.09%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.9340	93.40%
P-glycoprotein inhibitior	+	0.6453	64.53%
P-glycoprotein substrate	-	0.6455	64.55%
CYP3A4 substrate	+	0.6377	63.77%
CYP2C9 substrate	-	0.8108	81.08%
CYP2D6 substrate	-	0.8680	86.80%
CYP3A4 inhibition	-	0.8792	87.92%
CYP2C9 inhibition	-	0.8871	88.71%
CYP2C19 inhibition	-	0.8411	84.11%
CYP2D6 inhibition	-	0.9062	90.62%
CYP1A2 inhibition	-	0.6597	65.97%
CYP2C8 inhibition	+	0.6360	63.60%
CYP inhibitory promiscuity	-	0.8754	87.54%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7143	71.43%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.9134	91.34%
Skin irritation	-	0.8126	81.26%
Skin corrosion	-	0.9519	95.19%
Ames mutagenesis	+	0.5877	58.77%
Human Ether-a-go-go-Related Gene inhibition	-	0.3691	36.91%
Micronuclear	+	0.5418	54.18%
Hepatotoxicity	-	0.6375	63.75%
skin sensitisation	-	0.9163	91.63%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.6805	68.05%
Acute Oral Toxicity (c)	III	0.7012	70.12%
Estrogen receptor binding	+	0.7044	70.44%
Androgen receptor binding	-	0.4945	49.45%
Thyroid receptor binding	-	0.5593	55.93%
Glucocorticoid receptor binding	+	0.6186	61.86%
Aromatase binding	-	0.5803	58.03%
PPAR gamma	+	0.6103	61.03%
Honey bee toxicity	-	0.8520	85.20%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9657	96.57%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.51%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.33%	91.11%
CHEMBL220	P22303	Acetylcholinesterase	95.45%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.91%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.17%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	94.14%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.10%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.19%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	91.47%	91.49%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.77%	96.38%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.95%	99.17%
CHEMBL2535	P11166	Glucose transporter	89.71%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	89.52%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	88.41%	95.93%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.90%	96.00%
CHEMBL340	P08684	Cytochrome P450 3A4	85.48%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.48%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.33%	95.89%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.17%	96.90%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	81.81%	83.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.87%	94.00%
CHEMBL1811	P34995	Prostanoid EP1 receptor	80.30%	95.71%

Plants that contains it

• Rheum palmatum

Cross-Links

• PubChem: 163044751
• LOTUS: LTS0062642
• wikiData: Q105359654