Engeletin

Details

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Internal ID 2141b934-c13a-4fc2-8938-c9923f5429eb
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
IUPAC Name (2R,3R)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one
SMILES (Canonical) CC1C(C(C(C(O1)OC2C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](OC3=CC(=CC(=C3C2=O)O)O)C4=CC=C(C=C4)O)O)O)O
InChI InChI=1S/C21H22O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-25,27-28H,1H3/t8-,15-,17+,18+,19+,20-,21-/m0/s1
InChI Key VQUPQWGKORWZII-WDPYGAQVSA-N
Popularity 25 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 0.70
Atomic LogP (AlogP) 0.33
H-Bond Acceptor 10
H-Bond Donor 6
Rotatable Bonds 3

Synonyms

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572-31-6
Engelitin
3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (2R-trans)-
4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2R-trans)-
(2R,3R)-3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Aromadendrin 3-rhamnoside
Dihydrokaempferol 3-rhamnoside
MEGxp0_000364
SCHEMBL5575048
ACon1_000852
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Engeletin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8357 83.57%
Caco-2 - 0.8031 80.31%
Blood Brain Barrier - 0.8500 85.00%
Human oral bioavailability - 0.8286 82.86%
Subcellular localzation Mitochondria 0.7163 71.63%
OATP2B1 inhibitior - 0.5606 56.06%
OATP1B1 inhibitior + 0.8516 85.16%
OATP1B3 inhibitior + 0.9188 91.88%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior - 0.6111 61.11%
P-glycoprotein inhibitior - 0.6353 63.53%
P-glycoprotein substrate - 0.8262 82.62%
CYP3A4 substrate + 0.5983 59.83%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8557 85.57%
CYP3A4 inhibition - 0.7109 71.09%
CYP2C9 inhibition - 0.8538 85.38%
CYP2C19 inhibition - 0.8339 83.39%
CYP2D6 inhibition - 0.9547 95.47%
CYP1A2 inhibition - 0.5306 53.06%
CYP2C8 inhibition + 0.5000 50.00%
CYP inhibitory promiscuity - 0.5648 56.48%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6170 61.70%
Eye corrosion - 0.9885 98.85%
Eye irritation - 0.7479 74.79%
Skin irritation - 0.6220 62.20%
Skin corrosion - 0.9360 93.60%
Ames mutagenesis + 0.5700 57.00%
Human Ether-a-go-go-Related Gene inhibition - 0.5464 54.64%
Micronuclear + 0.9100 91.00%
Hepatotoxicity - 0.6467 64.67%
skin sensitisation - 0.8874 88.74%
Respiratory toxicity - 0.5444 54.44%
Reproductive toxicity + 0.7333 73.33%
Mitochondrial toxicity + 0.6250 62.50%
Nephrotoxicity + 0.5452 54.52%
Acute Oral Toxicity (c) III 0.5184 51.84%
Estrogen receptor binding + 0.6430 64.30%
Androgen receptor binding + 0.5974 59.74%
Thyroid receptor binding + 0.6344 63.44%
Glucocorticoid receptor binding + 0.6484 64.84%
Aromatase binding - 0.5185 51.85%
PPAR gamma + 0.6077 60.77%
Honey bee toxicity - 0.8167 81.67%
Biodegradation - 0.7250 72.50%
Crustacea aquatic toxicity + 0.5350 53.50%
Fish aquatic toxicity + 0.9457 94.57%

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 99.14% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 97.20% 91.49%
CHEMBL2581 P07339 Cathepsin D 94.41% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.09% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 93.31% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.96% 86.33%
CHEMBL3401 O75469 Pregnane X receptor 92.04% 94.73%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.13% 99.23%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 89.30% 96.09%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.20% 94.00%
CHEMBL4208 P20618 Proteasome component C5 86.48% 90.00%
CHEMBL2535 P11166 Glucose transporter 83.17% 98.75%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 82.73% 99.15%
CHEMBL3194 P02766 Transthyretin 81.42% 90.71%

Cross-Links

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PubChem 6453452
NPASS NPC177941
LOTUS LTS0068898
wikiData Q5377536