(2R)-5,6,8-trihydroxy-2-methyl-9-[(2R)-5,6,8-trihydroxy-2-methyl-4-oxo-2,3-dihydrobenzo[g]chromen-9-yl]-2,3-dihydrobenzo[g]chromen-4-one

Details

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Internal ID 13d6fd39-30a9-4411-bcf7-9594dcb89f5e
Taxonomy Organoheterocyclic compounds > Naphthopyrans > Naphthopyranones
IUPAC Name (2R)-5,6,8-trihydroxy-2-methyl-9-[(2R)-5,6,8-trihydroxy-2-methyl-4-oxo-2,3-dihydrobenzo[g]chromen-9-yl]-2,3-dihydrobenzo[g]chromen-4-one
SMILES (Canonical) CC1CC(=O)C2=C(O1)C=C3C(=C2O)C(=CC(=C3C4=C(C=C(C5=C(C6=C(C=C54)OC(CC6=O)C)O)O)O)O)O
SMILES (Isomeric) C[C@@H]1CC(=O)C2=C(O1)C=C3C(=C2O)C(=CC(=C3C4=C(C=C(C5=C(C6=C(C=C54)O[C@@H](CC6=O)C)O)O)O)O)O
InChI InChI=1S/C28H22O10/c1-9-3-13(29)25-19(37-9)5-11-21(15(31)7-17(33)23(11)27(25)35)22-12-6-20-26(14(30)4-10(2)38-20)28(36)24(12)18(34)8-16(22)32/h5-10,31-36H,3-4H2,1-2H3/t9-,10-/m1/s1
InChI Key JGQBYBXYRUCBQY-NXEZZACHSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H22O10
Molecular Weight 518.50 g/mol
Exact Mass 518.12129689 g/mol
Topological Polar Surface Area (TPSA) 174.00 Ų
XlogP 4.80
Atomic LogP (AlogP) 4.60
H-Bond Acceptor 10
H-Bond Donor 6
Rotatable Bonds 1

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R)-5,6,8-trihydroxy-2-methyl-9-[(2R)-5,6,8-trihydroxy-2-methyl-4-oxo-2,3-dihydrobenzo[g]chromen-9-yl]-2,3-dihydrobenzo[g]chromen-4-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8808 88.08%
Caco-2 - 0.6857 68.57%
Blood Brain Barrier - 0.7500 75.00%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.7966 79.66%
OATP2B1 inhibitior - 0.7155 71.55%
OATP1B1 inhibitior + 0.8882 88.82%
OATP1B3 inhibitior + 0.9624 96.24%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior - 0.5186 51.86%
P-glycoprotein inhibitior + 0.6167 61.67%
P-glycoprotein substrate - 0.7541 75.41%
CYP3A4 substrate - 0.5210 52.10%
CYP2C9 substrate - 0.7974 79.74%
CYP2D6 substrate - 0.7747 77.47%
CYP3A4 inhibition + 0.6155 61.55%
CYP2C9 inhibition + 0.7412 74.12%
CYP2C19 inhibition - 0.6022 60.22%
CYP2D6 inhibition - 0.8097 80.97%
CYP1A2 inhibition + 0.5874 58.74%
CYP2C8 inhibition - 0.9023 90.23%
CYP inhibitory promiscuity - 0.6181 61.81%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9600 96.00%
Carcinogenicity (trinary) Non-required 0.6364 63.64%
Eye corrosion - 0.9922 99.22%
Eye irritation - 0.7296 72.96%
Skin irritation - 0.7118 71.18%
Skin corrosion - 0.9065 90.65%
Ames mutagenesis + 0.5500 55.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6824 68.24%
Micronuclear + 0.7300 73.00%
Hepatotoxicity + 0.5355 53.55%
skin sensitisation - 0.9014 90.14%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.8889 88.89%
Mitochondrial toxicity + 0.7250 72.50%
Nephrotoxicity - 0.8040 80.40%
Acute Oral Toxicity (c) I 0.4061 40.61%
Estrogen receptor binding + 0.8194 81.94%
Androgen receptor binding + 0.6588 65.88%
Thyroid receptor binding + 0.5302 53.02%
Glucocorticoid receptor binding + 0.8080 80.80%
Aromatase binding + 0.5632 56.32%
PPAR gamma + 0.6607 66.07%
Honey bee toxicity - 0.8979 89.79%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.5100 51.00%
Fish aquatic toxicity + 0.9492 94.92%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL1287622 Q9Y468 Lethal(3)malignant brain tumor-like protein 1 631 nM
Potency
via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.34% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.37% 89.00%
CHEMBL2581 P07339 Cathepsin D 92.67% 98.95%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 92.01% 95.56%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 91.88% 94.80%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 89.69% 99.23%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 89.27% 85.14%
CHEMBL215 P09917 Arachidonate 5-lipoxygenase 87.83% 92.68%
CHEMBL1951 P21397 Monoamine oxidase A 86.36% 91.49%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.03% 94.45%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.50% 94.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 83.29% 96.09%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 83.19% 90.71%
CHEMBL241 Q14432 Phosphodiesterase 3A 82.71% 92.94%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.10% 100.00%
CHEMBL3401 O75469 Pregnane X receptor 81.75% 94.73%
CHEMBL2041 P07949 Tyrosine-protein kinase receptor RET 80.40% 91.79%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Arabidopsis thaliana
Astragalus mongholicus
Sesamum indicum

Cross-Links

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PubChem 40525734
NPASS NPC228908
LOTUS LTS0261112
wikiData Q105127609