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(4aR,12bS)-9-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-4a,7,8-trihydroxy-3-methyl-5,12b-dihydro-4H-benzo[a]anthracene-1,6-dione

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID 5e4dccbb-7c79-4df1-9b1e-3041394043ea
Taxonomy Benzenoids > Phenanthrenes and derivatives
IUPAC Name (4aR,12bS)-9-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-4a,7,8-trihydroxy-3-methyl-5,12b-dihydro-4H-benzo[a]anthracene-1,6-dione
SMILES (Canonical) CC1C(C(CC(O1)C2=C(C3=C(C4=C(C=C3C=C2)C5C(=O)C=C(CC5(CC4=O)O)C)O)O)O)O
SMILES (Isomeric) C[C@@H]1[C@H]([C@@H](C[C@@H](O1)C2=C(C3=C(C4=C(C=C3C=C2)[C@@H]5C(=O)C=C(C[C@]5(CC4=O)O)C)O)O)O)O
InChI InChI=1S/C25H26O8/c1-10-5-15(26)21-14-6-12-3-4-13(18-7-16(27)22(29)11(2)33-18)23(30)19(12)24(31)20(14)17(28)9-25(21,32)8-10/h3-6,11,16,18,21-22,27,29-32H,7-9H2,1-2H3/t11-,16-,18-,21-,22-,25-/m1/s1
InChI Key JLTQYLCHVIIOGK-ZQDNWLTESA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C25H26O8
Molecular Weight 454.50 g/mol
Exact Mass 454.16276778 g/mol
Topological Polar Surface Area (TPSA) 145.00 Ų
XlogP 0.90
Atomic LogP (AlogP) 2.14
H-Bond Acceptor 8
H-Bond Donor 5
Rotatable Bonds 1

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (4aR,12bS)-9-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]-4a,7,8-trihydroxy-3-methyl-5,12b-dihydro-4H-benzo[a]anthracene-1,6-dione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9339 93.39%
Caco-2 - 0.7418 74.18%
Blood Brain Barrier - 0.6379 63.79%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.5423 54.23%
OATP2B1 inhibitior - 0.7119 71.19%
OATP1B1 inhibitior + 0.8363 83.63%
OATP1B3 inhibitior + 0.9774 97.74%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior + 0.5973 59.73%
P-glycoprotein inhibitior - 0.6190 61.90%
P-glycoprotein substrate + 0.5619 56.19%
CYP3A4 substrate + 0.6757 67.57%
CYP2C9 substrate - 0.8019 80.19%
CYP2D6 substrate - 0.8590 85.90%
CYP3A4 inhibition - 0.6192 61.92%
CYP2C9 inhibition - 0.5449 54.49%
CYP2C19 inhibition - 0.6960 69.60%
CYP2D6 inhibition - 0.8622 86.22%
CYP1A2 inhibition - 0.6536 65.36%
CYP2C8 inhibition + 0.5000 50.00%
CYP inhibitory promiscuity - 0.7798 77.98%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5460 54.60%
Eye corrosion - 0.9916 99.16%
Eye irritation - 0.9238 92.38%
Skin irritation - 0.7123 71.23%
Skin corrosion - 0.9015 90.15%
Ames mutagenesis + 0.7300 73.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4449 44.49%
Micronuclear + 0.5700 57.00%
Hepatotoxicity + 0.5033 50.33%
skin sensitisation - 0.7711 77.11%
Respiratory toxicity + 0.7000 70.00%
Reproductive toxicity + 0.9889 98.89%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity - 0.6978 69.78%
Acute Oral Toxicity (c) I 0.5080 50.80%
Estrogen receptor binding + 0.7846 78.46%
Androgen receptor binding + 0.7325 73.25%
Thyroid receptor binding + 0.5445 54.45%
Glucocorticoid receptor binding + 0.7693 76.93%
Aromatase binding + 0.5803 58.03%
PPAR gamma + 0.6970 69.70%
Honey bee toxicity - 0.8454 84.54%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.5000 50.00%
Fish aquatic toxicity + 0.9820 98.20%

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 99.44% 91.11%
CHEMBL2581 P07339 Cathepsin D 96.50% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.69% 89.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 93.66% 85.14%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 92.21% 90.71%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.44% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.15% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.51% 86.33%
CHEMBL2553 Q15418 Ribosomal protein S6 kinase alpha 1 90.11% 85.11%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 89.30% 94.00%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.25% 99.23%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.82% 97.09%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 87.27% 96.21%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 86.50% 93.04%
CHEMBL2345 P51812 Ribosomal protein S6 kinase alpha 3 84.51% 95.64%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 84.33% 96.09%
CHEMBL3864 Q06124 Protein-tyrosine phosphatase 2C 83.87% 94.42%
CHEMBL1994 P08235 Mineralocorticoid receptor 83.80% 100.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 83.08% 95.89%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 81.81% 99.15%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 81.07% 97.33%
CHEMBL3830 Q2M2I8 Adaptor-associated kinase 80.01% 83.10%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 162932597
LOTUS LTS0197835
wikiData Q105131084