(3R)-5-[[(2R,3R,4S,5R,6S)-3,4-dihydroxy-6-[[(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-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

Details

Top
Internal ID 1bf20627-0184-4bd8-ab99-0a12bbab3bd5
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
IUPAC Name (3R)-5-[[(2R,3R,4S,5R,6S)-3,4-dihydroxy-6-[[(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-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) CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC(=C(C=C5)OC)O)O)COC(=O)CC(C)(CC(=O)O)O)O)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]([C@H]([C@H](O[C@H]2OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC(=C(C=C5)OC)O)O)COC(=O)C[C@@](C)(CC(=O)O)O)O)O)O)O)O
InChI InChI=1S/C34H42O19/c1-13-26(41)28(43)30(45)32(49-13)53-31-29(44)27(42)22(12-48-24(40)11-34(2,46)10-23(38)39)52-33(31)50-15-7-17(36)25-18(37)9-20(51-21(25)8-15)14-4-5-19(47-3)16(35)6-14/h4-8,13,20,22,26-33,35-36,41-46H,9-12H2,1-3H3,(H,38,39)/t13-,20-,22+,26-,27-,28+,29-,30+,31+,32-,33+,34+/m0/s1
InChI Key SHCWOSSXLGIQEQ-MDSOOJGZSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C34H42O19
Molecular Weight 754.70 g/mol
Exact Mass 754.23202911 g/mol
Topological Polar Surface Area (TPSA) 298.00 Ų
XlogP -1.50
Atomic LogP (AlogP) -0.99
H-Bond Acceptor 18
H-Bond Donor 9
Rotatable Bonds 12

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of (3R)-5-[[(2R,3R,4S,5R,6S)-3,4-dihydroxy-6-[[(2S)-5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-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

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6402 64.02%
Caco-2 - 0.8826 88.26%
Blood Brain Barrier - 0.7000 70.00%
Human oral bioavailability - 0.9000 90.00%
Subcellular localzation Mitochondria 0.5965 59.65%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8959 89.59%
OATP1B3 inhibitior + 0.9263 92.63%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.9000 90.00%
BSEP inhibitior + 0.6945 69.45%
P-glycoprotein inhibitior + 0.6449 64.49%
P-glycoprotein substrate + 0.6116 61.16%
CYP3A4 substrate + 0.7024 70.24%
CYP2C9 substrate - 0.8250 82.50%
CYP2D6 substrate - 0.8742 87.42%
CYP3A4 inhibition - 0.8520 85.20%
CYP2C9 inhibition - 0.9479 94.79%
CYP2C19 inhibition - 0.9394 93.94%
CYP2D6 inhibition - 0.9392 93.92%
CYP1A2 inhibition - 0.8684 86.84%
CYP2C8 inhibition + 0.7174 71.74%
CYP inhibitory promiscuity - 0.9490 94.90%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6153 61.53%
Eye corrosion - 0.9901 99.01%
Eye irritation - 0.9163 91.63%
Skin irritation - 0.8283 82.83%
Skin corrosion - 0.9489 94.89%
Ames mutagenesis - 0.7400 74.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6919 69.19%
Micronuclear + 0.5900 59.00%
Hepatotoxicity - 0.7551 75.51%
skin sensitisation - 0.9217 92.17%
Respiratory toxicity - 0.5889 58.89%
Reproductive toxicity + 0.8667 86.67%
Mitochondrial toxicity + 0.7375 73.75%
Nephrotoxicity - 0.9228 92.28%
Acute Oral Toxicity (c) III 0.5667 56.67%
Estrogen receptor binding + 0.8314 83.14%
Androgen receptor binding - 0.6607 66.07%
Thyroid receptor binding + 0.5238 52.38%
Glucocorticoid receptor binding + 0.6871 68.71%
Aromatase binding + 0.6107 61.07%
PPAR gamma + 0.7593 75.93%
Honey bee toxicity - 0.6774 67.74%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.6100 61.00%
Fish aquatic toxicity + 0.9628 96.28%

Targets

Top

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 99.28% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 98.74% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.44% 85.14%
CHEMBL2581 P07339 Cathepsin D 96.64% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.62% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 95.16% 89.00%
CHEMBL3714130 P46095 G-protein coupled receptor 6 92.52% 97.36%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 92.05% 94.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.72% 97.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 91.67% 99.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 91.35% 95.89%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.52% 95.56%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 86.72% 99.15%
CHEMBL3401 O75469 Pregnane X receptor 86.14% 94.73%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 86.06% 99.23%
CHEMBL4208 P20618 Proteasome component C5 85.53% 90.00%
CHEMBL5255 O00206 Toll-like receptor 4 84.78% 92.50%
CHEMBL2243 O00519 Anandamide amidohydrolase 83.18% 97.53%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 81.93% 97.33%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 80.68% 95.78%
CHEMBL215 P09917 Arachidonate 5-lipoxygenase 80.60% 92.68%
CHEMBL4481 P35228 Nitric oxide synthase, inducible 80.42% 94.80%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 80.14% 86.92%
CHEMBL1951 P21397 Monoamine oxidase A 80.07% 91.49%

Plants that contains it

Top
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

Top
PubChem 162910169
LOTUS LTS0120675
wikiData Q105252872