(2S)-2-[2-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one

Details

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Internal ID 16958bbf-ab04-4084-a022-65c62a7e80ee
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones
IUPAC Name (2S)-2-[2-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
SMILES (Canonical) CC1C(C(C(C(O1)OC2=C(C=C(C=C2)O)C3CC(=O)C4=C(C=C(C=C4O3)O)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(C=C(C=C2)O)[C@@H]3CC(=O)C4=C(C=C(C=C4O3)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
InChI InChI=1S/C27H32O15/c1-9-20(33)25(42-26-23(36)22(35)21(34)18(8-28)41-26)24(37)27(38-9)40-15-3-2-10(29)4-12(15)16-7-14(32)19-13(31)5-11(30)6-17(19)39-16/h2-6,9,16,18,20-31,33-37H,7-8H2,1H3/t9-,16-,18+,20-,21+,22-,23+,24+,25+,26-,27-/m0/s1
InChI Key JTQOVBLCPLYXBN-VDBSBOKISA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C27H32O15
Molecular Weight 596.50 g/mol
Exact Mass 596.17412031 g/mol
Topological Polar Surface Area (TPSA) 245.00 Ų
XlogP -0.90
Atomic LogP (AlogP) -1.46
H-Bond Acceptor 15
H-Bond Donor 9
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2S)-2-[2-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-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 - 0.9049 90.49%
Blood Brain Barrier - 0.8250 82.50%
Human oral bioavailability - 0.9000 90.00%
Subcellular localzation Mitochondria 0.6881 68.81%
OATP2B1 inhibitior - 0.8484 84.84%
OATP1B1 inhibitior + 0.9065 90.65%
OATP1B3 inhibitior + 0.9552 95.52%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior + 0.6699 66.99%
P-glycoprotein inhibitior - 0.7227 72.27%
P-glycoprotein substrate - 0.5409 54.09%
CYP3A4 substrate + 0.6499 64.99%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8479 84.79%
CYP3A4 inhibition - 0.9358 93.58%
CYP2C9 inhibition - 0.9271 92.71%
CYP2C19 inhibition - 0.9330 93.30%
CYP2D6 inhibition - 0.9643 96.43%
CYP1A2 inhibition - 0.8830 88.30%
CYP2C8 inhibition + 0.5805 58.05%
CYP inhibitory promiscuity - 0.7188 71.88%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7023 70.23%
Eye corrosion - 0.9927 99.27%
Eye irritation - 0.9272 92.72%
Skin irritation - 0.8192 81.92%
Skin corrosion - 0.9626 96.26%
Ames mutagenesis - 0.6600 66.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6480 64.80%
Micronuclear + 0.6433 64.33%
Hepatotoxicity - 0.6000 60.00%
skin sensitisation - 0.9312 93.12%
Respiratory toxicity - 0.5000 50.00%
Reproductive toxicity + 0.7333 73.33%
Mitochondrial toxicity - 0.5250 52.50%
Nephrotoxicity - 0.7548 75.48%
Acute Oral Toxicity (c) III 0.5734 57.34%
Estrogen receptor binding + 0.8014 80.14%
Androgen receptor binding - 0.5641 56.41%
Thyroid receptor binding + 0.5329 53.29%
Glucocorticoid receptor binding - 0.4831 48.31%
Aromatase binding - 0.5129 51.29%
PPAR gamma + 0.7024 70.24%
Honey bee toxicity - 0.6984 69.84%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5850 58.50%
Fish aquatic toxicity + 0.8289 82.89%

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 99.09% 91.11%
CHEMBL2581 P07339 Cathepsin D 97.36% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.82% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.18% 86.33%
CHEMBL1806 P11388 DNA topoisomerase II alpha 94.78% 89.00%
CHEMBL4208 P20618 Proteasome component C5 90.62% 90.00%
CHEMBL3060 Q9Y345 Glycine transporter 2 89.43% 99.17%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.16% 95.89%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.42% 95.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.57% 94.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 86.70% 94.45%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.47% 97.09%
CHEMBL3401 O75469 Pregnane X receptor 84.64% 94.73%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 83.90% 90.71%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.44% 95.89%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 82.22% 86.92%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 81.47% 99.15%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 81.12% 96.21%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 80.64% 95.78%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.56% 99.23%

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.
Thelypteris acuminata

Cross-Links

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PubChem 11995074
LOTUS LTS0048855
wikiData Q105134940