5,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one

Details

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Internal ID 6033a6df-4f17-42c5-914d-232dadd968bb
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
IUPAC Name 5,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
SMILES (Canonical) CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=C(C3=O)C(=C(C=C4)O)O)C5=CC(=C(C=C5)O)OC)O)O)O)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=C(C3=O)C(=C(C=C4)O)O)C5=CC(=C(C=C5)O)OC)O)O)O)O)O)O
InChI InChI=1S/C28H32O16/c1-9-17(31)21(35)23(37)27(41-9)40-8-15-19(33)22(36)24(38)28(43-15)44-26-20(34)16-13(6-5-12(30)18(16)32)42-25(26)10-3-4-11(29)14(7-10)39-2/h3-7,9,15,17,19,21-24,27-33,35-38H,8H2,1-2H3/t9-,15+,17-,19+,21+,22-,23+,24+,27+,28-/m0/s1
InChI Key YPVHXSHTDWFNMH-ZIXFLESYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C28H32O16
Molecular Weight 624.50 g/mol
Exact Mass 624.16903493 g/mol
Topological Polar Surface Area (TPSA) 255.00 Ų
XlogP -1.00
Atomic LogP (AlogP) -1.38
H-Bond Acceptor 16
H-Bond Donor 9
Rotatable Bonds 7

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 5,6-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.4777 47.77%
Caco-2 - 0.9288 92.88%
Blood Brain Barrier - 0.9250 92.50%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.6902 69.02%
OATP2B1 inhibitior - 0.5796 57.96%
OATP1B1 inhibitior + 0.8890 88.90%
OATP1B3 inhibitior + 0.9479 94.79%
MATE1 inhibitior - 0.7800 78.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.5835 58.35%
P-glycoprotein inhibitior - 0.5974 59.74%
P-glycoprotein substrate - 0.5285 52.85%
CYP3A4 substrate + 0.6151 61.51%
CYP2C9 substrate - 0.7502 75.02%
CYP2D6 substrate - 0.8538 85.38%
CYP3A4 inhibition - 0.8619 86.19%
CYP2C9 inhibition - 0.9071 90.71%
CYP2C19 inhibition - 0.9025 90.25%
CYP2D6 inhibition - 0.9231 92.31%
CYP1A2 inhibition - 0.9045 90.45%
CYP2C8 inhibition + 0.7860 78.60%
CYP inhibitory promiscuity - 0.6670 66.70%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.6995 69.95%
Eye corrosion - 0.9891 98.91%
Eye irritation - 0.9138 91.38%
Skin irritation - 0.8249 82.49%
Skin corrosion - 0.9594 95.94%
Ames mutagenesis - 0.5892 58.92%
Human Ether-a-go-go-Related Gene inhibition - 0.4463 44.63%
Micronuclear + 0.7492 74.92%
Hepatotoxicity - 0.5948 59.48%
skin sensitisation - 0.9436 94.36%
Respiratory toxicity + 0.5111 51.11%
Reproductive toxicity + 0.8111 81.11%
Mitochondrial toxicity - 0.6625 66.25%
Nephrotoxicity - 0.9665 96.65%
Acute Oral Toxicity (c) III 0.6904 69.04%
Estrogen receptor binding + 0.8333 83.33%
Androgen receptor binding + 0.5724 57.24%
Thyroid receptor binding + 0.5217 52.17%
Glucocorticoid receptor binding + 0.6774 67.74%
Aromatase binding + 0.5891 58.91%
PPAR gamma + 0.7333 73.33%
Honey bee toxicity - 0.7695 76.95%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5549 55.49%
Fish aquatic toxicity + 0.8477 84.77%

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%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 98.13% 94.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 96.86% 89.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 96.16% 86.33%
CHEMBL2581 P07339 Cathepsin D 95.58% 98.95%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.37% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.96% 96.09%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 91.99% 99.15%
CHEMBL1951 P21397 Monoamine oxidase A 91.05% 91.49%
CHEMBL3401 O75469 Pregnane X receptor 88.66% 94.73%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.59% 99.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.20% 95.56%
CHEMBL3714130 P46095 G-protein coupled receptor 6 85.40% 97.36%
CHEMBL2345 P51812 Ribosomal protein S6 kinase alpha 3 84.56% 95.64%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 83.55% 96.00%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 82.13% 90.71%
CHEMBL4306 P22460 Voltage-gated potassium channel subunit Kv1.5 81.39% 94.03%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 80.14% 94.45%

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.
Morinda citrifolia

Cross-Links

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PubChem 163037816
LOTUS LTS0149810
wikiData Q105351879