Robinetin

Details

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Internal ID 62f86acc-ca26-47f9-aaa3-8cee895ffddb
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavones > Flavonols
IUPAC Name 3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
SMILES (Canonical) C1=CC2=C(C=C1O)OC(=C(C2=O)O)C3=CC(=C(C(=C3)O)O)O
SMILES (Isomeric) C1=CC2=C(C=C1O)OC(=C(C2=O)O)C3=CC(=C(C(=C3)O)O)O
InChI InChI=1S/C15H10O7/c16-7-1-2-8-11(5-7)22-15(14(21)12(8)19)6-3-9(17)13(20)10(18)4-6/h1-5,16-18,20-21H
InChI Key SOEDEYVDCDYMMH-UHFFFAOYSA-N
Popularity 196 references in papers

Physical and Chemical Properties

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Molecular Formula C15H10O7
Molecular Weight 302.23 g/mol
Exact Mass 302.04265265 g/mol
Topological Polar Surface Area (TPSA) 127.00 Ų
XlogP 1.60
Atomic LogP (AlogP) 1.99
H-Bond Acceptor 7
H-Bond Donor 5
Rotatable Bonds 1

Synonyms

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490-31-3
3,7-Dihydroxy-2-(3,4,5-trihydroxyphenyl)-4H-chromen-4-one
Norkanugin
5-Hydroxyfisetin
5-Deoxymyricetin
4H-1-Benzopyran-4-one, 3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-
3,3',4',5',7-Pentahydroxyflavone
3,7,3',4',5'-pentahydroxyflavone
3,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chromen-4-one
NSC 407331
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Robinetin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9071 90.71%
Caco-2 - 0.8152 81.52%
Blood Brain Barrier - 0.7750 77.50%
Human oral bioavailability + 0.5714 57.14%
Subcellular localzation Mitochondria 0.5892 58.92%
OATP2B1 inhibitior + 0.5358 53.58%
OATP1B1 inhibitior + 0.9052 90.52%
OATP1B3 inhibitior + 0.9480 94.80%
MATE1 inhibitior - 0.7400 74.00%
OCT2 inhibitior - 0.9750 97.50%
BSEP inhibitior - 0.7512 75.12%
P-glycoprotein inhibitior - 0.9045 90.45%
P-glycoprotein substrate - 0.6713 67.13%
CYP3A4 substrate - 0.5400 54.00%
CYP2C9 substrate - 0.8321 83.21%
CYP2D6 substrate - 0.8118 81.18%
CYP3A4 inhibition + 0.6951 69.51%
CYP2C9 inhibition - 0.5823 58.23%
CYP2C19 inhibition - 0.9025 90.25%
CYP2D6 inhibition - 0.9287 92.87%
CYP1A2 inhibition + 0.9106 91.06%
CYP2C8 inhibition + 0.7366 73.66%
CYP inhibitory promiscuity + 0.5822 58.22%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6750 67.50%
Eye corrosion - 0.9905 99.05%
Eye irritation + 0.9517 95.17%
Skin irritation + 0.5835 58.35%
Skin corrosion - 0.9397 93.97%
Ames mutagenesis - 0.6700 67.00%
Human Ether-a-go-go-Related Gene inhibition - 0.8418 84.18%
Micronuclear + 0.9300 93.00%
Hepatotoxicity + 0.7625 76.25%
skin sensitisation - 0.7447 74.47%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.5875 58.75%
Nephrotoxicity - 0.7570 75.70%
Acute Oral Toxicity (c) II 0.7348 73.48%
Estrogen receptor binding + 0.8687 86.87%
Androgen receptor binding + 0.8952 89.52%
Thyroid receptor binding + 0.5994 59.94%
Glucocorticoid receptor binding + 0.8862 88.62%
Aromatase binding + 0.8395 83.95%
PPAR gamma + 0.8626 86.26%
Honey bee toxicity - 0.9269 92.69%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5300 53.00%
Fish aquatic toxicity + 0.9124 91.24%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL1293236 P46063 ATP-dependent DNA helicase Q1 4466.8 nM
Potency
via CMAUP
CHEMBL4660 P28907 Lymphocyte differentiation antigen CD38 37900 nM
IC50
PMID: 21641214
CHEMBL3004 P33527 Multidrug resistance-associated protein 1 5000 nM
Ki
PMID: 19725578
CHEMBL1075138 Q9NUW8 Tyrosyl-DNA phosphodiesterase 1 281.8 nM
281.8 nM
Potency
Potency
via Super-PRED
via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.53% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.31% 89.00%
CHEMBL1951 P21397 Monoamine oxidase A 91.46% 91.49%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 91.45% 94.00%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 91.25% 99.15%
CHEMBL3194 P02766 Transthyretin 90.54% 90.71%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.28% 95.56%
CHEMBL2581 P07339 Cathepsin D 90.05% 98.95%
CHEMBL3401 O75469 Pregnane X receptor 86.48% 94.73%
CHEMBL1293255 P15428 15-hydroxyprostaglandin dehydrogenase [NAD+] 85.75% 83.57%
CHEMBL242 Q92731 Estrogen receptor beta 84.97% 98.35%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 84.21% 99.23%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.04% 94.45%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 83.81% 90.71%
CHEMBL1293249 Q13887 Kruppel-like factor 5 83.03% 86.33%
CHEMBL3038469 P24941 CDK2/Cyclin A 82.33% 91.38%

Cross-Links

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PubChem 5281692
NPASS NPC74881
ChEMBL CHEMBL170405
LOTUS LTS0171492
wikiData Q27108166