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(1S)-1,5-Anhydro-1-C-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-3,5,7-trihydroxy-2H-1-benzopyran-8-yl]-D-glucitol

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 21c4aca3-8ba2-41f5-991f-6c9993c82b36
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides
IUPAC Name (2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
SMILES (Canonical) C1C(C(OC2=C1C(=CC(=C2C3C(C(C(C(O3)CO)O)O)O)O)O)C4=CC(=C(C=C4)O)O)O
SMILES (Isomeric) C1[C@H]([C@H](OC2=C1C(=CC(=C2[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O)C4=CC(=C(C=C4)O)O)O
InChI InChI=1S/C21H24O11/c22-6-14-16(28)17(29)18(30)21(31-14)15-12(26)5-10(24)8-4-13(27)19(32-20(8)15)7-1-2-9(23)11(25)3-7/h1-3,5,13-14,16-19,21-30H,4,6H2/t13-,14-,16-,17+,18-,19-,21+/m1/s1
InChI Key XWDHVYPMZCGHNM-SBNMIOBJSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C21H24O11
Molecular Weight 452.40 g/mol
Exact Mass 452.13186158 g/mol
Topological Polar Surface Area (TPSA) 201.00 Ų
XlogP -1.00
Atomic LogP (AlogP) -0.94
H-Bond Acceptor 11
H-Bond Donor 9
Rotatable Bonds 3

Synonyms

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(1S)-1,5-Anhydro-1-C-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-3,5,7-trihydroxy-2H-1-benzopyran-8-yl]-D-glucitol
103215-48-1

2D Structure

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2D Structure of (1S)-1,5-Anhydro-1-C-[(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-3,5,7-trihydroxy-2H-1-benzopyran-8-yl]-D-glucitol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.6354 63.54%
Caco-2 - 0.9069 90.69%
Blood Brain Barrier - 0.6250 62.50%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Nucleus 0.4480 44.80%
OATP2B1 inhibitior - 0.5632 56.32%
OATP1B1 inhibitior + 0.8828 88.28%
OATP1B3 inhibitior + 0.9713 97.13%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.8000 80.00%
BSEP inhibitior - 0.7163 71.63%
P-glycoprotein inhibitior - 0.7368 73.68%
P-glycoprotein substrate - 0.8414 84.14%
CYP3A4 substrate + 0.5371 53.71%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate + 0.3508 35.08%
CYP3A4 inhibition - 0.9014 90.14%
CYP2C9 inhibition - 0.9446 94.46%
CYP2C19 inhibition - 0.9185 91.85%
CYP2D6 inhibition - 0.9166 91.66%
CYP1A2 inhibition - 0.9124 91.24%
CYP2C8 inhibition - 0.5825 58.25%
CYP inhibitory promiscuity - 0.8647 86.47%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6685 66.85%
Eye corrosion - 0.9943 99.43%
Eye irritation - 0.8386 83.86%
Skin irritation - 0.7763 77.63%
Skin corrosion - 0.9580 95.80%
Ames mutagenesis + 0.6064 60.64%
Human Ether-a-go-go-Related Gene inhibition + 0.7293 72.93%
Micronuclear + 0.6159 61.59%
Hepatotoxicity - 0.8802 88.02%
skin sensitisation - 0.8594 85.94%
Respiratory toxicity + 0.6111 61.11%
Reproductive toxicity + 0.7667 76.67%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity - 0.7604 76.04%
Acute Oral Toxicity (c) III 0.4032 40.32%
Estrogen receptor binding - 0.4783 47.83%
Androgen receptor binding + 0.6438 64.38%
Thyroid receptor binding + 0.6094 60.94%
Glucocorticoid receptor binding - 0.5831 58.31%
Aromatase binding - 0.5000 50.00%
PPAR gamma + 0.6512 65.12%
Honey bee toxicity - 0.8221 82.21%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5700 57.00%
Fish aquatic toxicity - 0.4731 47.31%

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 99.65% 91.11%
CHEMBL4040 P28482 MAP kinase ERK2 96.45% 83.82%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.33% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.70% 97.09%
CHEMBL1951 P21397 Monoamine oxidase A 93.23% 91.49%
CHEMBL3401 O75469 Pregnane X receptor 89.79% 94.73%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.34% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.94% 95.56%
CHEMBL2581 P07339 Cathepsin D 85.44% 98.95%
CHEMBL226 P30542 Adenosine A1 receptor 82.52% 95.93%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 81.81% 99.15%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.13% 95.89%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 21626717
LOTUS LTS0143994
wikiData Q105343320