(3R,5R)-1,3,5-trihydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylic acid

Details

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Internal ID b3affc7c-a207-4a66-8fc1-f702834cb110
Taxonomy Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
IUPAC Name (3R,5R)-1,3,5-trihydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylic acid
SMILES (Canonical) C1C(C(C(CC1(C(=O)O)O)O)C(=O)C=CC2=CC=C(C=C2)O)O
SMILES (Isomeric) C1[C@H](C([C@@H](CC1(C(=O)O)O)O)C(=O)/C=C/C2=CC=C(C=C2)O)O
InChI InChI=1S/C16H18O7/c17-10-4-1-9(2-5-10)3-6-11(18)14-12(19)7-16(23,15(21)22)8-13(14)20/h1-6,12-14,17,19-20,23H,7-8H2,(H,21,22)/b6-3+/t12-,13-,14?,16?/m1/s1
InChI Key LDKXJGREMRAESV-FWDXKVTKSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C16H18O7
Molecular Weight 322.31 g/mol
Exact Mass 322.10525291 g/mol
Topological Polar Surface Area (TPSA) 135.00 Ų
XlogP 0.20
Atomic LogP (AlogP) -0.08
H-Bond Acceptor 6
H-Bond Donor 5
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (3R,5R)-1,3,5-trihydroxy-4-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]cyclohexane-1-carboxylic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8326 83.26%
Caco-2 - 0.8865 88.65%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.6286 62.86%
Subcellular localzation Mitochondria 0.7058 70.58%
OATP2B1 inhibitior - 0.7214 72.14%
OATP1B1 inhibitior + 0.9419 94.19%
OATP1B3 inhibitior + 0.9548 95.48%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8588 85.88%
BSEP inhibitior - 0.9061 90.61%
P-glycoprotein inhibitior - 0.9657 96.57%
P-glycoprotein substrate - 0.8238 82.38%
CYP3A4 substrate - 0.5269 52.69%
CYP2C9 substrate - 0.7887 78.87%
CYP2D6 substrate - 0.8603 86.03%
CYP3A4 inhibition - 0.8655 86.55%
CYP2C9 inhibition - 0.9378 93.78%
CYP2C19 inhibition - 0.9470 94.70%
CYP2D6 inhibition - 0.9547 95.47%
CYP1A2 inhibition - 0.9629 96.29%
CYP2C8 inhibition - 0.6633 66.33%
CYP inhibitory promiscuity - 0.9832 98.32%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.8821 88.21%
Carcinogenicity (trinary) Non-required 0.6146 61.46%
Eye corrosion - 0.9908 99.08%
Eye irritation - 0.8707 87.07%
Skin irritation - 0.5798 57.98%
Skin corrosion - 0.8823 88.23%
Ames mutagenesis - 0.8300 83.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6791 67.91%
Micronuclear + 0.6000 60.00%
Hepatotoxicity - 0.6277 62.77%
skin sensitisation - 0.5714 57.14%
Respiratory toxicity + 0.6000 60.00%
Reproductive toxicity + 0.6111 61.11%
Mitochondrial toxicity + 0.5500 55.00%
Nephrotoxicity - 0.5644 56.44%
Acute Oral Toxicity (c) III 0.7508 75.08%
Estrogen receptor binding + 0.7278 72.78%
Androgen receptor binding + 0.6662 66.62%
Thyroid receptor binding + 0.5185 51.85%
Glucocorticoid receptor binding + 0.6745 67.45%
Aromatase binding - 0.5533 55.33%
PPAR gamma + 0.5288 52.88%
Honey bee toxicity - 0.9073 90.73%
Biodegradation - 0.6250 62.50%
Crustacea aquatic toxicity - 0.6500 65.00%
Fish aquatic toxicity + 0.9759 97.59%

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 97.80% 91.11%
CHEMBL2179 P04062 Beta-glucocerebrosidase 89.75% 85.31%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.76% 95.56%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 88.00% 96.09%
CHEMBL206 P03372 Estrogen receptor alpha 87.89% 97.64%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.60% 89.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.76% 97.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 84.44% 86.33%
CHEMBL4208 P20618 Proteasome component C5 84.06% 90.00%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 83.73% 94.45%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 83.71% 94.62%
CHEMBL3194 P02766 Transthyretin 83.66% 90.71%
CHEMBL2563 Q9UQL6 Histone deacetylase 5 83.53% 89.67%
CHEMBL242 Q92731 Estrogen receptor beta 83.22% 98.35%
CHEMBL4227 P25090 Lipoxin A4 receptor 81.66% 100.00%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 81.09% 96.00%

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.
Humulus lupulus

Cross-Links

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PubChem 101639422
NPASS NPC7157