Cynarine

Details

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Internal ID cc2a2c5e-b084-484f-a1d9-2cce482b2941
Taxonomy Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
IUPAC Name (1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
SMILES (Canonical) C1C(C(C(CC1(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O)O
SMILES (Isomeric) C1[C@H]([C@@H]([C@@H](C[C@]1(C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)O)O
InChI InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
InChI Key YDDUMTOHNYZQPO-RVXRWRFUSA-N
Popularity 102 references in papers

Physical and Chemical Properties

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Molecular Formula C25H24O12
Molecular Weight 516.40 g/mol
Exact Mass 516.12677620 g/mol
Topological Polar Surface Area (TPSA) 211.00 Ų
XlogP 1.50
Atomic LogP (AlogP) 1.03
H-Bond Acceptor 11
H-Bond Donor 7
Rotatable Bonds 7

Synonyms

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Cynarine
Cinarine
30964-13-7
Cinarin
1,5-Dicaffeoylquinic acid
1,3-Dicaffeoylquinic acid
Cynarine [INN]
Plemocil
1,3-Dicqa
Phemocil
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Cynarine

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9316 93.16%
Caco-2 - 0.9089 90.89%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.8005 80.05%
OATP2B1 inhibitior - 0.7088 70.88%
OATP1B1 inhibitior + 0.9492 94.92%
OATP1B3 inhibitior + 0.9502 95.02%
MATE1 inhibitior - 0.7200 72.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.7252 72.52%
P-glycoprotein inhibitior - 0.4291 42.91%
P-glycoprotein substrate - 0.8245 82.45%
CYP3A4 substrate + 0.5567 55.67%
CYP2C9 substrate + 0.6016 60.16%
CYP2D6 substrate - 0.8522 85.22%
CYP3A4 inhibition - 0.9109 91.09%
CYP2C9 inhibition - 0.9219 92.19%
CYP2C19 inhibition - 0.8849 88.49%
CYP2D6 inhibition - 0.9442 94.42%
CYP1A2 inhibition - 0.8691 86.91%
CYP2C8 inhibition + 0.5306 53.06%
CYP inhibitory promiscuity - 0.9763 97.63%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.8664 86.64%
Carcinogenicity (trinary) Non-required 0.5584 55.84%
Eye corrosion - 0.9917 99.17%
Eye irritation - 0.9005 90.05%
Skin irritation - 0.7017 70.17%
Skin corrosion - 0.9105 91.05%
Ames mutagenesis - 0.8300 83.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3669 36.69%
Micronuclear + 0.5800 58.00%
Hepatotoxicity + 0.6375 63.75%
skin sensitisation - 0.6487 64.87%
Respiratory toxicity + 0.5333 53.33%
Reproductive toxicity + 0.6778 67.78%
Mitochondrial toxicity + 0.6375 63.75%
Nephrotoxicity - 0.8853 88.53%
Acute Oral Toxicity (c) III 0.7458 74.58%
Estrogen receptor binding + 0.7161 71.61%
Androgen receptor binding + 0.7728 77.28%
Thyroid receptor binding + 0.5671 56.71%
Glucocorticoid receptor binding + 0.6883 68.83%
Aromatase binding - 0.5626 56.26%
PPAR gamma + 0.5581 55.81%
Honey bee toxicity - 0.8245 82.45%
Biodegradation - 0.7000 70.00%
Crustacea aquatic toxicity - 0.6355 63.55%
Fish aquatic toxicity + 0.9945 99.45%

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 99.61% 91.11%
CHEMBL1951 P21397 Monoamine oxidase A 96.94% 91.49%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.38% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.66% 86.33%
CHEMBL3194 P02766 Transthyretin 92.58% 90.71%
CHEMBL221 P23219 Cyclooxygenase-1 91.64% 90.17%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 91.44% 94.45%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 90.98% 96.00%
CHEMBL1806 P11388 DNA topoisomerase II alpha 90.82% 89.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.70% 95.56%
CHEMBL1821 P08173 Muscarinic acetylcholine receptor M4 89.43% 94.08%
CHEMBL245 P20309 Muscarinic acetylcholine receptor M3 88.63% 97.53%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 88.43% 94.62%
CHEMBL4208 P20618 Proteasome component C5 87.59% 90.00%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 85.34% 99.15%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 85.20% 95.50%
CHEMBL3137262 O60341 LSD1/CoREST complex 83.69% 97.09%
CHEMBL216 P11229 Muscarinic acetylcholine receptor M1 83.11% 94.23%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 82.98% 94.97%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 81.79% 91.07%
CHEMBL340 P08684 Cytochrome P450 3A4 80.36% 91.19%

Cross-Links

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PubChem 5281769
NPASS NPC284948
ChEMBL CHEMBL487258
LOTUS LTS0039940
wikiData Q1763092