(1R,3R,4S,5R)-3-[(Z)-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid

Details

Top
Internal ID 865ca1fd-a862-4a5f-8151-60916cb3b3f6
Taxonomy Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
IUPAC Name (1R,3R,4S,5R)-3-[(Z)-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
SMILES (Canonical) C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=O)C(=O)C=C2)O)O
SMILES (Isomeric) C1[C@H]([C@@H]([C@@H](C[C@]1(C(=O)O)O)OC(=O)/C=C\C2=CC(=O)C(=O)C=C2)O)O
InChI InChI=1S/C16H16O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,19,21,24H,6-7H2,(H,22,23)/b4-2-/t11-,12-,14+,16-/m1/s1
InChI Key ITENTBHADJNDDH-DJTMHQFBSA-N
Popularity 0 references in papers

Physical and Chemical Properties

Top
Molecular Formula C16H16O9
Molecular Weight 352.29 g/mol
Exact Mass 352.07943208 g/mol
Topological Polar Surface Area (TPSA) 158.00 Ų
XlogP -1.70
Atomic LogP (AlogP) -1.58
H-Bond Acceptor 8
H-Bond Donor 4
Rotatable Bonds 4

Synonyms

Top
There are no found synonyms.

2D Structure

Top
2D Structure of (1R,3R,4S,5R)-3-[(Z)-3-(3,4-dioxocyclohexa-1,5-dien-1-yl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid

3D Structure

Top

ADMET Properties (via admetSAR 2)

Top
Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.7565 75.65%
Caco-2 - 0.9321 93.21%
Blood Brain Barrier + 0.5250 52.50%
Human oral bioavailability - 0.5286 52.86%
Subcellular localzation Mitochondria 0.8117 81.17%
OATP2B1 inhibitior - 0.8595 85.95%
OATP1B1 inhibitior + 0.9472 94.72%
OATP1B3 inhibitior + 0.9392 93.92%
MATE1 inhibitior - 0.8800 88.00%
OCT2 inhibitior - 0.8838 88.38%
BSEP inhibitior - 0.8454 84.54%
P-glycoprotein inhibitior - 0.9223 92.23%
P-glycoprotein substrate - 0.7379 73.79%
CYP3A4 substrate + 0.6074 60.74%
CYP2C9 substrate - 0.8019 80.19%
CYP2D6 substrate - 0.8818 88.18%
CYP3A4 inhibition - 0.9626 96.26%
CYP2C9 inhibition - 0.8960 89.60%
CYP2C19 inhibition - 0.8825 88.25%
CYP2D6 inhibition - 0.9388 93.88%
CYP1A2 inhibition - 0.9477 94.77%
CYP2C8 inhibition - 0.8329 83.29%
CYP inhibitory promiscuity - 0.9699 96.99%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9243 92.43%
Carcinogenicity (trinary) Non-required 0.6303 63.03%
Eye corrosion - 0.9877 98.77%
Eye irritation - 0.9530 95.30%
Skin irritation - 0.6788 67.88%
Skin corrosion - 0.9305 93.05%
Ames mutagenesis - 0.7000 70.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6105 61.05%
Micronuclear + 0.5200 52.00%
Hepatotoxicity + 0.5250 52.50%
skin sensitisation - 0.6544 65.44%
Respiratory toxicity + 0.6778 67.78%
Reproductive toxicity + 0.6889 68.89%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity - 0.7199 71.99%
Acute Oral Toxicity (c) III 0.5379 53.79%
Estrogen receptor binding + 0.6318 63.18%
Androgen receptor binding + 0.5799 57.99%
Thyroid receptor binding - 0.6241 62.41%
Glucocorticoid receptor binding + 0.5920 59.20%
Aromatase binding - 0.5000 50.00%
PPAR gamma - 0.5629 56.29%
Honey bee toxicity - 0.8121 81.21%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.6700 67.00%
Fish aquatic toxicity + 0.9402 94.02%

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 97.66% 91.11%
CHEMBL221 P23219 Cyclooxygenase-1 93.91% 90.17%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 90.98% 94.23%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 90.13% 94.08%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 87.80% 96.09%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 87.37% 94.97%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 87.14% 95.56%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.85% 89.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 84.64% 94.45%
CHEMBL4208 P20618 Proteasome component C5 83.60% 90.00%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 83.46% 94.62%
CHEMBL1293249 Q13887 Kruppel-like factor 5 82.73% 86.33%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 82.42% 85.14%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 81.08% 95.50%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 80.82% 96.00%
CHEMBL279 P35968 Vascular endothelial growth factor receptor 2 80.74% 95.52%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 80.05% 99.23%
CHEMBL340 P08684 Cytochrome P450 3A4 80.00% 91.19%

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.
Cynara cardunculus

Cross-Links

Top
PubChem 163028953
LOTUS LTS0263555
wikiData Q105119994