5,7-dihydroxy-2-(4-hydroxyphenyl)-3,8-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one

Details

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Internal ID 67a0cdfe-0035-4219-afbf-b67484b54531
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-8-O-glycosides
IUPAC Name 5,7-dihydroxy-2-(4-hydroxyphenyl)-3,8-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
SMILES (Canonical) C1=CC(=CC=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)OC4C(C(C(C(O4)CO)O)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
SMILES (Isomeric) C1=CC(=CC=C1C2=C(C(=O)C3=C(O2)C(=C(C=C3O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
InChI InChI=1S/C27H30O17/c28-6-12-15(33)18(36)20(38)26(40-12)43-23-11(32)5-10(31)14-17(35)25(22(42-24(14)23)8-1-3-9(30)4-2-8)44-27-21(39)19(37)16(34)13(7-29)41-27/h1-5,12-13,15-16,18-21,26-34,36-39H,6-7H2/t12-,13-,15-,16-,18+,19+,20-,21-,26+,27+/m1/s1
InChI Key VMOKZQAQPBUNRW-PXJYGDGDSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C27H30O17
Molecular Weight 626.50 g/mol
Exact Mass 626.14829948 g/mol
Topological Polar Surface Area (TPSA) 286.00 Ų
XlogP -1.40
Atomic LogP (AlogP) -3.07
H-Bond Acceptor 17
H-Bond Donor 11
Rotatable Bonds 7

Synonyms

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99224-12-1
HERBACETIN-3,8-DIGLUCOPYRANOSIDE
Herbacetin 3,8-O-diglucoside
CHEMBL596219
5,7-dihydroxy-2-(4-hydroxyphenyl)-3,8-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
5,7-dihydroxy-2-(4-hydroxyphenyl)-3,8-bis[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
Herbacetin 3,8-diglucoside
DTXSID70912828
CHEBI:191048
BDBM50304345
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of 5,7-dihydroxy-2-(4-hydroxyphenyl)-3,8-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-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 - 0.5736 57.36%
Caco-2 - 0.9183 91.83%
Blood Brain Barrier - 0.7500 75.00%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.5848 58.48%
OATP2B1 inhibitior - 0.5553 55.53%
OATP1B1 inhibitior + 0.9116 91.16%
OATP1B3 inhibitior + 0.9434 94.34%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior + 0.6094 60.94%
P-glycoprotein inhibitior - 0.4679 46.79%
P-glycoprotein substrate - 0.8171 81.71%
CYP3A4 substrate + 0.5694 56.94%
CYP2C9 substrate - 0.6762 67.62%
CYP2D6 substrate - 0.8575 85.75%
CYP3A4 inhibition - 0.9390 93.90%
CYP2C9 inhibition - 0.9315 93.15%
CYP2C19 inhibition - 0.9047 90.47%
CYP2D6 inhibition - 0.9458 94.58%
CYP1A2 inhibition - 0.9180 91.80%
CYP2C8 inhibition + 0.6860 68.60%
CYP inhibitory promiscuity - 0.7526 75.26%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6848 68.48%
Eye corrosion - 0.9930 99.30%
Eye irritation - 0.8673 86.73%
Skin irritation - 0.8255 82.55%
Skin corrosion - 0.9691 96.91%
Ames mutagenesis + 0.5346 53.46%
Human Ether-a-go-go-Related Gene inhibition + 0.6914 69.14%
Micronuclear + 0.6433 64.33%
Hepatotoxicity - 0.6196 61.96%
skin sensitisation - 0.9132 91.32%
Respiratory toxicity + 0.5556 55.56%
Reproductive toxicity + 0.7111 71.11%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity - 0.6435 64.35%
Acute Oral Toxicity (c) IV 0.4763 47.63%
Estrogen receptor binding + 0.7676 76.76%
Androgen receptor binding + 0.6752 67.52%
Thyroid receptor binding - 0.5421 54.21%
Glucocorticoid receptor binding - 0.5545 55.45%
Aromatase binding + 0.5531 55.31%
PPAR gamma + 0.6915 69.15%
Honey bee toxicity - 0.7520 75.20%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.6450 64.50%
Fish aquatic toxicity + 0.7958 79.58%

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 99.42% 91.11%
CHEMBL2581 P07339 Cathepsin D 94.80% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.57% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 94.45% 94.00%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 90.37% 99.15%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.90% 94.45%
CHEMBL3401 O75469 Pregnane X receptor 88.67% 94.73%
CHEMBL3060 Q9Y345 Glycine transporter 2 88.10% 99.17%
CHEMBL2345 P51812 Ribosomal protein S6 kinase alpha 3 86.18% 95.64%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.71% 86.33%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 84.59% 86.92%
CHEMBL3194 P02766 Transthyretin 83.89% 90.71%
CHEMBL3137262 O60341 LSD1/CoREST complex 82.56% 97.09%
CHEMBL242 Q92731 Estrogen receptor beta 82.15% 98.35%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 81.80% 95.78%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 80.02% 95.56%

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.
Rhodiola rosea

Cross-Links

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PubChem 5491604
NPASS NPC8573
ChEMBL CHEMBL596219
LOTUS LTS0226544
wikiData Q82883243