1,8-dihydroxy-3-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-10H-anthracen-9-one

Details

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Internal ID f24e8e0c-e1b1-499f-960d-6017da5f5c71
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
IUPAC Name 1,8-dihydroxy-3-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-10H-anthracen-9-one
SMILES (Canonical) COC1=CC2=C(C(=C1)O)C(=O)C3=C(C=CC(=C3C2)OC4C(C(C(C(O4)CO)O)O)O)O
SMILES (Isomeric) COC1=CC2=C(C(=C1)O)C(=O)C3=C(C=CC(=C3C2)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
InChI InChI=1S/C21H22O10/c1-29-9-4-8-5-10-13(30-21-20(28)19(27)17(25)14(7-22)31-21)3-2-11(23)16(10)18(26)15(8)12(24)6-9/h2-4,6,14,17,19-25,27-28H,5,7H2,1H3/t14-,17-,19+,20-,21-/m1/s1
InChI Key IPGXIZABQUBQSI-IAAKTDFRSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H22O10
Molecular Weight 434.40 g/mol
Exact Mass 434.12129689 g/mol
Topological Polar Surface Area (TPSA) 166.00 Ų
XlogP 1.00
Atomic LogP (AlogP) -0.58
H-Bond Acceptor 10
H-Bond Donor 6
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 1,8-dihydroxy-3-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-10H-anthracen-9-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.4880 48.80%
Caco-2 - 0.8303 83.03%
Blood Brain Barrier - 0.8000 80.00%
Human oral bioavailability - 0.8000 80.00%
Subcellular localzation Mitochondria 0.5216 52.16%
OATP2B1 inhibitior - 0.5622 56.22%
OATP1B1 inhibitior + 0.9129 91.29%
OATP1B3 inhibitior + 0.9680 96.80%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior - 0.6406 64.06%
P-glycoprotein inhibitior - 0.7667 76.67%
P-glycoprotein substrate - 0.8282 82.82%
CYP3A4 substrate + 0.5807 58.07%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8282 82.82%
CYP3A4 inhibition - 0.8798 87.98%
CYP2C9 inhibition - 0.9239 92.39%
CYP2C19 inhibition - 0.9061 90.61%
CYP2D6 inhibition - 0.9244 92.44%
CYP1A2 inhibition - 0.7540 75.40%
CYP2C8 inhibition - 0.6357 63.57%
CYP inhibitory promiscuity - 0.7550 75.50%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7039 70.39%
Eye corrosion - 0.9882 98.82%
Eye irritation - 0.9116 91.16%
Skin irritation - 0.8089 80.89%
Skin corrosion - 0.9618 96.18%
Ames mutagenesis + 0.6536 65.36%
Human Ether-a-go-go-Related Gene inhibition - 0.5000 50.00%
Micronuclear + 0.6233 62.33%
Hepatotoxicity - 0.6823 68.23%
skin sensitisation - 0.9167 91.67%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.5250 52.50%
Nephrotoxicity + 0.5672 56.72%
Acute Oral Toxicity (c) III 0.7077 70.77%
Estrogen receptor binding + 0.7062 70.62%
Androgen receptor binding + 0.5296 52.96%
Thyroid receptor binding + 0.5362 53.62%
Glucocorticoid receptor binding + 0.6581 65.81%
Aromatase binding + 0.5758 57.58%
PPAR gamma + 0.6629 66.29%
Honey bee toxicity - 0.8213 82.13%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.7049 70.49%
Fish aquatic toxicity + 0.6972 69.72%

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 99.26% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.87% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 94.09% 95.56%
CHEMBL2581 P07339 Cathepsin D 92.62% 98.95%
CHEMBL4208 P20618 Proteasome component C5 92.30% 90.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 91.18% 94.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 91.10% 99.17%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 91.09% 99.15%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 91.05% 96.21%
CHEMBL3401 O75469 Pregnane X receptor 90.00% 94.73%
CHEMBL3137262 O60341 LSD1/CoREST complex 89.94% 97.09%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.94% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.52% 89.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 87.81% 85.14%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.93% 94.45%
CHEMBL1951 P21397 Monoamine oxidase A 84.52% 91.49%
CHEMBL220 P22303 Acetylcholinesterase 82.67% 94.45%
CHEMBL2535 P11166 Glucose transporter 80.39% 98.75%
CHEMBL1293249 Q13887 Kruppel-like factor 5 80.32% 86.33%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.27% 95.89%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.08% 99.23%

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.
Swertia japonica

Cross-Links

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PubChem 162850791
LOTUS LTS0146173
wikiData Q105117246