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(3Z,5S)-5-hydroxy-4-(4-hydroxyphenyl)-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6-dihydro-1-benzoxocin-2-one

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 58c7a0dc-e062-423f-9c67-88c4cac509a9
Taxonomy Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
IUPAC Name (3Z,5S)-5-hydroxy-4-(4-hydroxyphenyl)-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6-dihydro-1-benzoxocin-2-one
SMILES (Canonical) C1C(C(=CC(=O)OC2=C1C=CC(=C2)OC3C(C(C(C(O3)CO)O)O)O)C4=CC=C(C=C4)O)O
SMILES (Isomeric) C1[C@@H](/C(=C\C(=O)OC2=C1C=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)/C4=CC=C(C=C4)O)O
InChI InChI=1S/C23H24O10/c24-10-18-20(28)21(29)22(30)23(33-18)31-14-6-3-12-7-16(26)15(9-19(27)32-17(12)8-14)11-1-4-13(25)5-2-11/h1-6,8-9,16,18,20-26,28-30H,7,10H2/b15-9-/t16-,18+,20+,21-,22+,23+/m0/s1
InChI Key BFKUDGRBSUJNLA-LRYVSMNUSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C23H24O10
Molecular Weight 460.40 g/mol
Exact Mass 460.13694696 g/mol
Topological Polar Surface Area (TPSA) 166.00 Ų
XlogP -0.40
Atomic LogP (AlogP) -0.52
H-Bond Acceptor 10
H-Bond Donor 6
Rotatable Bonds 4

Synonyms

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(3Z,5S)-5-hydroxy-4-(4-hydroxyphenyl)-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6-dihydro-1-benzoxocin-2-one
126589-95-5
AKOS040762361

2D Structure

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2D Structure of (3Z,5S)-5-hydroxy-4-(4-hydroxyphenyl)-9-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,6-dihydro-1-benzoxocin-2-one

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7565 75.65%
Caco-2 - 0.9177 91.77%
Blood Brain Barrier - 0.6500 65.00%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.5363 53.63%
OATP2B1 inhibitior - 0.5628 56.28%
OATP1B1 inhibitior + 0.8980 89.80%
OATP1B3 inhibitior + 0.9366 93.66%
MATE1 inhibitior - 0.9600 96.00%
OCT2 inhibitior - 0.8500 85.00%
BSEP inhibitior + 0.6671 66.71%
P-glycoprotein inhibitior - 0.6695 66.95%
P-glycoprotein substrate - 0.8160 81.60%
CYP3A4 substrate + 0.6375 63.75%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8695 86.95%
CYP3A4 inhibition - 0.9135 91.35%
CYP2C9 inhibition - 0.8682 86.82%
CYP2C19 inhibition - 0.8442 84.42%
CYP2D6 inhibition - 0.8602 86.02%
CYP1A2 inhibition - 0.8468 84.68%
CYP2C8 inhibition + 0.6567 65.67%
CYP inhibitory promiscuity - 0.6913 69.13%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.7246 72.46%
Eye corrosion - 0.9919 99.19%
Eye irritation - 0.9050 90.50%
Skin irritation - 0.7865 78.65%
Skin corrosion - 0.9572 95.72%
Ames mutagenesis - 0.5900 59.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4055 40.55%
Micronuclear + 0.6333 63.33%
Hepatotoxicity - 0.7750 77.50%
skin sensitisation - 0.8307 83.07%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity + 0.5750 57.50%
Nephrotoxicity - 0.6594 65.94%
Acute Oral Toxicity (c) III 0.4176 41.76%
Estrogen receptor binding + 0.7197 71.97%
Androgen receptor binding + 0.5691 56.91%
Thyroid receptor binding - 0.4921 49.21%
Glucocorticoid receptor binding - 0.5636 56.36%
Aromatase binding + 0.5538 55.38%
PPAR gamma + 0.7617 76.17%
Honey bee toxicity - 0.7537 75.37%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5650 56.50%
Fish aquatic toxicity + 0.9184 91.84%

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 96.41% 98.95%
CHEMBL220 P22303 Acetylcholinesterase 94.98% 94.45%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 94.32% 94.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 94.22% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.22% 86.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 91.94% 99.17%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 91.76% 95.89%
CHEMBL5608 Q16288 NT-3 growth factor receptor 91.60% 95.89%
CHEMBL5339 Q5NUL3 G-protein coupled receptor 120 91.25% 95.78%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 91.25% 96.09%
CHEMBL1951 P21397 Monoamine oxidase A 91.17% 91.49%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 89.05% 99.15%
CHEMBL2288 Q13526 Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 87.39% 91.71%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.79% 94.45%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.28% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.93% 89.00%
CHEMBL2243 O00519 Anandamide amidohydrolase 83.34% 97.53%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 83.17% 90.71%
CHEMBL6175 Q9H3R0 Lysine-specific demethylase 4C 83.04% 96.69%
CHEMBL4208 P20618 Proteasome component C5 81.92% 90.00%
CHEMBL1994 P08235 Mineralocorticoid receptor 81.66% 100.00%
CHEMBL3401 O75469 Pregnane X receptor 81.10% 94.73%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 80.50% 85.00%

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.
Ononis speciosa

Cross-Links

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PubChem 6442480
LOTUS LTS0142559
wikiData Q104934341