Cynarine

Details

• 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
• 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: 143 references in papers

Physical and Chemical Properties

• 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

• Cynarine
• Cinarine
• Cinarin
• Plemocil
• Listrocol
• 1,3-Dicqa
• 85D81U9JAV
• Caffeic acid 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene ester
• 1-carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate)
• (1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
• 3,4-Dihydroxycinnamic acid 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene ester
• 3,4-Dihydroxycinnamic acid, 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene ester
• (1R,3R,4S,5R)-1,3-Bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-4,5-dihydroxycyclohexanecarboxylic acid
• Cyclohexanecarboxylic acid, 1,3-bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-4,5-dihydroxy-, (1R,3R,4S,5R)-
• (1R-(1alpha,3alpha,4alpha,5beta))-1,3-Bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-4,5-dihydroxycyclohexanecarboxylic acid
• cynarinum
• cynarix
• (1R,3R,4S,5R)-1,3-bis(((E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl)oxy)-4,5-dihydroxycyclohexane-1-carboxylic acid
• (1R,3R,4S,5R)-1,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-4,5-dihydroxycyclohexanecarboxylic acid
• RefChem:34327
• 1,3-Dicaffeoylquinic acid (constituent of echinacea angustifolia root, echinacea pallida root, echinacea purpurea root and echinacea purpurea aerial parts)
• 1884-24-8
• Cinarina
• 1,3-Dicaffeoylquinic acid
• Cynarine [INN]
• 212891-05-9
• (1R,3R,4S,5R)-1,3-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexanecarboxylic acid
• Cynarine [MI]
• Cynarine [MART.]
• Cynarine [WHO-DD]
• 1,5-di-O-Caffeoylquinic acid
• Cyclohexanecarboxylic acid,1,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-4,5-dihydroxy-,(1R,3R,4S,5R)-
• 1884-23-7
• Phemocil
• (1R,3R,4S,5R)-1,3-bis(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexane-1-carboxylic acid
• CAS-30964-13-7
• 1,5-Dicaffeoylqunic acid
• 1,5-DQA
• UNII-85D81U9JAV
• Quinic acid 1,5-dicaffeic ester
• Cynarin (Standard)
• Cynarine [INN:WHO-DD]
• Cynarin, analytical standard
• 1,5-Dicaffeoyl quinic acid
• SCHEMBL42528
• CHEBI:520
• 1_5_dihydrocaffeoylquinic_acid
• CHEMBL487258
• orb1300209
• SCHEMBL29921198
• SCHEMBL30267017
• HY-N0359R
• YDDUMTOHNYZQPO-RVXRWRFUSA-N
• DTXSID301309674
• GLXC-07328
• HMS6018M12
• HY-N0359
• Tox21_111176
• BDBM50369484
• MSK170155
• s3301
• AKOS015912727
• Tox21_111176_1
• AC-6022
• CS-6280
• NCGC00274085-01
• AS-74959
• DA-49032
• DA-52251
• FD157793
• FD157794
• NS00007039
• 1,3-Dicaffeoylquinic acid, >=98% (HPLC)
• Q1763092
• (1R,3R,4S,5R)-1,3-Bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexanecarboxylicacid
• (1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxy-cyclohexanecarboxylic acid
• (1R,3R,4S,5R)-1,3-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxycyclohexane-1-carboxylic acid
• (1R-(1.ALPHA.,3.ALPHA.,4.ALPHA.,5.BETA.))-1,3-BIS((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-4,5-DIHYDROXYCYCLOHEXANECARBOXYLIC ACID
• Cinarine; (1R,3R,4S,5R)-1,3-bis[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-4,5-dihydroxy-cyclohexanecarboxylic acid
• Cyclohexanecarboxylic acid, 1,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-4,5-dihydroxy-

2D Structure

ADMET Properties (via admetSAR 2)

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

Proven Targets:

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%

Plants that contains it

• Achillea clypeolata
• Arctium lappa
• Artemisia argyi
• Artemisia montana
• Artemisia princeps
• Athanasia crithmifolia
• Berberis julianae
• Bridelia ferruginea
• Bystropogon origanifolius
• Cardamine heptaphylla
• Centella asiatica
• Cerbera odollam
• Chrysanthemum indicum
• Cichorium intybus
• Cichorium pumilum
• Cneorum pulverulentum
• Codonocarpus attenuatus
• Colchicum soboliferum
• Crateva magna
• Cynara cardunculus
• Dalea elegans
• Diospyros verrucosa
• Erigeron breviscapus
• Euonymus nanoides
• Foeniculum vulgare
• Inula japonica
• Ipomoea batatas
• Jacobaea subalpina
• Nepeta multifida
• Pentanema britannicum
• Pleogyne australis
• Polygala amara
• Psorodendron spinosum
• Pyrola decorata
• Quercus serrata
• Rubus allegheniensis
• Salvia abrotanoides
• Sarcandra glabra
• Saussurea involucrata
• Stephania sutchuenensis
• Swertia japonica
• Tetraneuris acaulis
• Trachelospermum asiaticum
• Unonopsis glaucopetala
• Xanthium strumarium
• Xanthium strumarium subsp. strumarium
• Zieria smithii

Cross-Links

• PubChem: 5281769
• NPASS: NPC284948
• ChEMBL: CHEMBL487258
• LOTUS: LTS0039940
• wikiData: Q1763092