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

Details

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Internal ID 10ade59f-f53b-4090-b5ec-b2bc3fb5d903
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-(oxalooxymethyl)oxan-2-yl]oxyanthracene-2-carboxylic acid
SMILES (Canonical) C1=CC2=C(C(=C1)OC3C(C(C(C(O3)COC(=O)C(=O)O)O)O)O)C(=O)C4=C(C2=O)C=C(C=C4O)C(=O)O
SMILES (Isomeric) C1=CC2=C(C(=C1)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)COC(=O)C(=O)O)O)O)O)C(=O)C4=C(C2=O)C=C(C=C4O)C(=O)O
InChI InChI=1S/C23H18O14/c24-10-5-7(20(30)31)4-9-13(10)17(27)14-8(15(9)25)2-1-3-11(14)36-23-19(29)18(28)16(26)12(37-23)6-35-22(34)21(32)33/h1-5,12,16,18-19,23-24,26,28-29H,6H2,(H,30,31)(H,32,33)/t12-,16-,18+,19-,23-/m1/s1
InChI Key DQJNCXBYABUAPU-ASFVZVPISA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C23H18O14
Molecular Weight 518.40 g/mol
Exact Mass 518.06965524 g/mol
Topological Polar Surface Area (TPSA) 234.00 Ų
XlogP 0.40
Atomic LogP (AlogP) -1.32
H-Bond Acceptor 12
H-Bond Donor 6
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 4-hydroxy-9,10-dioxo-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(oxalooxymethyl)oxan-2-yl]oxyanthracene-2-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.6172 61.72%
Caco-2 - 0.9253 92.53%
Blood Brain Barrier - 0.7250 72.50%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.5513 55.13%
OATP2B1 inhibitior - 0.5541 55.41%
OATP1B1 inhibitior + 0.8994 89.94%
OATP1B3 inhibitior + 0.9040 90.40%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.6750 67.50%
BSEP inhibitior + 0.6813 68.13%
P-glycoprotein inhibitior + 0.6022 60.22%
P-glycoprotein substrate - 0.7527 75.27%
CYP3A4 substrate + 0.6045 60.45%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8795 87.95%
CYP3A4 inhibition - 0.8995 89.95%
CYP2C9 inhibition - 0.8583 85.83%
CYP2C19 inhibition - 0.8769 87.69%
CYP2D6 inhibition - 0.9452 94.52%
CYP1A2 inhibition - 0.8764 87.64%
CYP2C8 inhibition + 0.6031 60.31%
CYP inhibitory promiscuity - 0.8791 87.91%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6864 68.64%
Eye corrosion - 0.9920 99.20%
Eye irritation - 0.8408 84.08%
Skin irritation - 0.8129 81.29%
Skin corrosion - 0.9635 96.35%
Ames mutagenesis + 0.5377 53.77%
Human Ether-a-go-go-Related Gene inhibition - 0.3734 37.34%
Micronuclear + 0.6992 69.92%
Hepatotoxicity - 0.6125 61.25%
skin sensitisation - 0.8914 89.14%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.8333 83.33%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity + 0.6445 64.45%
Acute Oral Toxicity (c) III 0.5057 50.57%
Estrogen receptor binding + 0.6449 64.49%
Androgen receptor binding - 0.4893 48.93%
Thyroid receptor binding - 0.6053 60.53%
Glucocorticoid receptor binding + 0.5374 53.74%
Aromatase binding - 0.6434 64.34%
PPAR gamma + 0.5910 59.10%
Honey bee toxicity - 0.8369 83.69%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.7550 75.50%
Fish aquatic toxicity + 0.9222 92.22%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 96.19% 91.11%
CHEMBL2581 P07339 Cathepsin D 96.12% 98.95%
CHEMBL226 P30542 Adenosine A1 receptor 95.46% 95.93%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.62% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.47% 86.33%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 94.43% 99.23%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.13% 95.56%
CHEMBL1951 P21397 Monoamine oxidase A 92.56% 91.49%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 91.78% 96.38%
CHEMBL3194 P02766 Transthyretin 89.74% 90.71%
CHEMBL1811 P34995 Prostanoid EP1 receptor 89.24% 95.71%
CHEMBL3401 O75469 Pregnane X receptor 88.23% 94.73%
CHEMBL2535 P11166 Glucose transporter 87.11% 98.75%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 86.67% 96.09%
CHEMBL3475 P05121 Plasminogen activator inhibitor-1 86.50% 83.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 86.20% 99.17%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 85.67% 96.00%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 83.38% 99.15%
CHEMBL5608 Q16288 NT-3 growth factor receptor 81.09% 95.89%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.64% 95.50%

Cross-Links

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PubChem 11972451
NPASS NPC36959