methyl (1R,3R,4S,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylate

Details

Top
Internal ID bbdca0d3-6b66-40db-bc5f-fc97c9eb404a
Taxonomy Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
IUPAC Name methyl (1R,3R,4S,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylate
SMILES (Canonical) COC(=O)C1(CC(C(C(C1)OC(=O)C=CC2=CC=C(C=C2)O)O)O)O
SMILES (Isomeric) COC(=O)[C@]1(C[C@H]([C@@H]([C@@H](C1)OC(=O)/C=C/C2=CC=C(C=C2)O)O)O)O
InChI InChI=1S/C17H20O8/c1-24-16(22)17(23)8-12(19)15(21)13(9-17)25-14(20)7-4-10-2-5-11(18)6-3-10/h2-7,12-13,15,18-19,21,23H,8-9H2,1H3/b7-4+/t12-,13-,15+,17-/m1/s1
InChI Key WZYLCZULUZFCHF-UEHMLNNNSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C17H20O8
Molecular Weight 352.30 g/mol
Exact Mass 352.11581759 g/mol
Topological Polar Surface Area (TPSA) 134.00 Ų
XlogP 0.30
Atomic LogP (AlogP) -0.26
H-Bond Acceptor 8
H-Bond Donor 4
Rotatable Bonds 4

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of methyl (1R,3R,4S,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylate

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8483 84.83%
Caco-2 - 0.8280 82.80%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.7857 78.57%
Subcellular localzation Mitochondria 0.7302 73.02%
OATP2B1 inhibitior - 0.8587 85.87%
OATP1B1 inhibitior + 0.9329 93.29%
OATP1B3 inhibitior + 0.9420 94.20%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.8338 83.38%
BSEP inhibitior + 0.5656 56.56%
P-glycoprotein inhibitior - 0.8478 84.78%
P-glycoprotein substrate - 0.6433 64.33%
CYP3A4 substrate + 0.6116 61.16%
CYP2C9 substrate - 0.7984 79.84%
CYP2D6 substrate - 0.8434 84.34%
CYP3A4 inhibition - 0.8918 89.18%
CYP2C9 inhibition - 0.8717 87.17%
CYP2C19 inhibition - 0.8952 89.52%
CYP2D6 inhibition - 0.9429 94.29%
CYP1A2 inhibition - 0.8568 85.68%
CYP2C8 inhibition + 0.4710 47.10%
CYP inhibitory promiscuity - 0.9709 97.09%
UGT catelyzed + 0.8000 80.00%
Carcinogenicity (binary) - 0.9243 92.43%
Carcinogenicity (trinary) Non-required 0.5906 59.06%
Eye corrosion - 0.9907 99.07%
Eye irritation - 0.9212 92.12%
Skin irritation - 0.6858 68.58%
Skin corrosion - 0.8950 89.50%
Ames mutagenesis - 0.7400 74.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3908 39.08%
Micronuclear + 0.5800 58.00%
Hepatotoxicity + 0.5243 52.43%
skin sensitisation - 0.7589 75.89%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.6889 68.89%
Mitochondrial toxicity + 0.6000 60.00%
Nephrotoxicity - 0.7905 79.05%
Acute Oral Toxicity (c) III 0.6851 68.51%
Estrogen receptor binding + 0.7395 73.95%
Androgen receptor binding + 0.6514 65.14%
Thyroid receptor binding - 0.4947 49.47%
Glucocorticoid receptor binding + 0.7227 72.27%
Aromatase binding - 0.5848 58.48%
PPAR gamma - 0.5094 50.94%
Honey bee toxicity - 0.8380 83.80%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.5600 56.00%
Fish aquatic toxicity + 0.9619 96.19%

Targets

Top

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 98.87% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.55% 96.09%
CHEMBL4040 P28482 MAP kinase ERK2 93.02% 83.82%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.52% 94.45%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 90.89% 96.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.79% 95.56%
CHEMBL2179 P04062 Beta-glucocerebrosidase 89.22% 85.31%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.92% 85.14%
CHEMBL4208 P20618 Proteasome component C5 88.22% 90.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 87.14% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.99% 86.33%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 84.92% 94.97%
CHEMBL245 P20309 Muscarinic acetylcholine receptor M3 83.70% 97.53%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.18% 89.00%
CHEMBL2581 P07339 Cathepsin D 82.59% 98.95%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.18% 95.50%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.09% 95.89%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 81.39% 95.89%
CHEMBL2535 P11166 Glucose transporter 80.77% 98.75%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 80.37% 94.08%
CHEMBL221 P23219 Cyclooxygenase-1 80.15% 90.17%

Plants that contains it

Top
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.
Platycladus orientalis

Cross-Links

Top
PubChem 21626501
LOTUS LTS0266901
wikiData Q105323647