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(3R)-5-[[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-[[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid

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 4e27f4ae-c6e2-45eb-ad54-96560901e9f1
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
IUPAC Name (3R)-5-[[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-[[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C33H40O18/c1-13-25(40)27(42)29(44)31(47-13)51-30-28(43)26(41)21(12-46-23(39)11-33(2,45)10-22(37)38)50-32(30)48-16-7-17(35)24-18(36)9-19(49-20(24)8-16)14-3-5-15(34)6-4-14/h3-8,13,19,21,25-32,34-35,40-45H,9-12H2,1-2H3,(H,37,38)/t13-,19-,21+,25-,26+,27+,28-,29+,30+,31-,32+,33+/m0/s1
InChI Key NEFQWEGQYZRALY-PTGODMJLSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C33H40O18
Molecular Weight 724.70 g/mol
Exact Mass 724.22146442 g/mol
Topological Polar Surface Area (TPSA) 289.00 Ų
XlogP -1.50
Atomic LogP (AlogP) -1.00
H-Bond Acceptor 17
H-Bond Donor 9
Rotatable Bonds 11

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3R)-5-[[(2R,3S,4S,5R,6S)-3,4-dihydroxy-6-[[(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydrochromen-7-yl]oxy]-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6425 64.25%
Caco-2 - 0.8851 88.51%
Blood Brain Barrier - 0.7250 72.50%
Human oral bioavailability - 0.9143 91.43%
Subcellular localzation Mitochondria 0.6984 69.84%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8895 88.95%
OATP1B3 inhibitior + 0.9356 93.56%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.7162 71.62%
P-glycoprotein inhibitior + 0.5863 58.63%
P-glycoprotein substrate + 0.5203 52.03%
CYP3A4 substrate + 0.6968 69.68%
CYP2C9 substrate - 0.8250 82.50%
CYP2D6 substrate - 0.8742 87.42%
CYP3A4 inhibition - 0.8490 84.90%
CYP2C9 inhibition - 0.9303 93.03%
CYP2C19 inhibition - 0.9165 91.65%
CYP2D6 inhibition - 0.9442 94.42%
CYP1A2 inhibition - 0.8712 87.12%
CYP2C8 inhibition + 0.6719 67.19%
CYP inhibitory promiscuity - 0.9405 94.05%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6341 63.41%
Eye corrosion - 0.9918 99.18%
Eye irritation - 0.9182 91.82%
Skin irritation - 0.8232 82.32%
Skin corrosion - 0.9456 94.56%
Ames mutagenesis - 0.6800 68.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6690 66.90%
Micronuclear + 0.6000 60.00%
Hepatotoxicity - 0.7801 78.01%
skin sensitisation - 0.9154 91.54%
Respiratory toxicity + 0.5222 52.22%
Reproductive toxicity + 0.8444 84.44%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity - 0.9070 90.70%
Acute Oral Toxicity (c) III 0.5598 55.98%
Estrogen receptor binding + 0.8320 83.20%
Androgen receptor binding - 0.5295 52.95%
Thyroid receptor binding - 0.5099 50.99%
Glucocorticoid receptor binding + 0.6504 65.04%
Aromatase binding + 0.5872 58.72%
PPAR gamma + 0.7413 74.13%
Honey bee toxicity - 0.7025 70.25%
Biodegradation - 0.7750 77.50%
Crustacea aquatic toxicity - 0.6200 62.00%
Fish aquatic toxicity + 0.9802 98.02%

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 99.60% 91.11%
CHEMBL2581 P07339 Cathepsin D 97.88% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.50% 96.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.30% 89.00%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.14% 85.14%
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.14% 86.33%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.06% 97.09%
CHEMBL3714130 P46095 G-protein coupled receptor 6 92.19% 97.36%
CHEMBL3401 O75469 Pregnane X receptor 92.00% 94.73%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 89.20% 99.15%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.80% 99.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.55% 95.56%
CHEMBL5608 Q16288 NT-3 growth factor receptor 88.23% 95.89%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 87.35% 94.80%
CHEMBL5255 O00206 Toll-like receptor 4 87.13% 92.50%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 85.76% 99.23%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 85.10% 94.00%
CHEMBL4208 P20618 Proteasome component C5 84.91% 90.00%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 83.79% 85.00%
CHEMBL215 P09917 Arachidonate 5-lipoxygenase 82.00% 92.68%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 81.49% 97.33%
CHEMBL2345 P51812 Ribosomal protein S6 kinase alpha 3 80.26% 95.64%
CHEMBL2243 O00519 Anandamide amidohydrolase 80.17% 97.53%

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.
Citrus × aurantium

Cross-Links

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PubChem 124871748
LOTUS LTS0248206
wikiData Q105177900