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3,4-dicaffeoyl quinic acid

Family: Plantae - Asteraceae-Compositae
Kingdom: Plantae
Class: Phenolic
- Subclass: Quinic Acid Derivative

Canonical Smiles	O=C(O[C@@H]1[C@@H](O)C[C@@](C[C@@H]1OC(=O)/C=C/c1ccc(c(c1)O)O)(O)C(=O)O)/C=C/c1ccc(c(c1)O)O
InChI	InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(35,24(33)34)11-19(30)23(20)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20-,23+,25-/m0/s1
InChIKey	UFCLZKMFXSILNL-KDBOUVDRSA-N
Formula	C₂₅H₂₄O₁₂
HBA	11
HBD	7
MW	516.46
Rotatable Bonds	7
TPSA	211.28
LogP	1.03
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	37
Formal Charge	0
Fraction CSP3	0.24
Exact Mass	516.13
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Erigeron floribundus	Asteraceae-Compositae	Plantae	91244

Showing of synonyms

Berto C, Maggi F, et al. (2014). Phenolic constituents of Erigeron floribundus (Asteraceae), a Cameroonian medicinal plant.. Natural Product Communications, 2014, 9(12), 1691-1964. [View] [PubMed]

Pubchem: 10324242

Zinc: ZINC000038517271

Nmrshiftdb2: 70002594

Chembl: CHEMBL453537

No compound-protein relationship available.

SMILES: c1ccccc1C=CC(=O)OC2C(CCCC2)OC(=O)C=Cc3ccccc3

Level: 2

Mol. Weight: 516.46 g/mol

SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 516.46 g/mol

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 516.46 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 516.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.83
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.77
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: -2.76

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.81
Plasma Protein Binding: 80.16
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.47
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.9
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.63
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 5.72
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: -455.56
Rat (Acute): 2.2
Rat (Chronic Oral): 3.62
Fathead Minnow: 3.91
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 585.59
Hydration Free Energy: -3.12
Log(D) at pH=7.4: 0.08
Log(P): 1.43
Log S: -2.82
Log(Vapor Pressure): -15.05
Melting Point: 257.34
pKa Acid: 5.09
pKa Basic: 5.87

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.9357
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	3	0.9317
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.9129
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9088
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9065
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8767
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8739
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8701
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8682
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8674
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8518
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8426
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.8374
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8344
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.8325
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	3	0.8323
Nucleoside diphosphate kinase	Q2SWE7	NDK_BURTA	Burkholderia thailandensis	3	0.8316
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.8298
Ectonucleoside triphosphate diphosphohydrolase I	Q5ZUA2	Q5ZUA2_LEGPH	Legionella pneumophila subsp. pneumophila	3	0.8250
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8223
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.8215
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8098
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8048
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	4	0.8016
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.8013
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7955
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7919
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7907
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.7900
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7868
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7822
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7807
Bromodomain-containing protein 2	P25440	BRD2_HUMAN	Homo sapiens	3	0.7805
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7773
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7746
[Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 2, mitochondrial	Q15119	PDK2_HUMAN	Homo sapiens	4	0.7741
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7719
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7698
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.7698
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	2	0.7664
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7663
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7646
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7625
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7584
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7580
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7579
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7575
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7561
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7560
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7535
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7500
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7497
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	4	0.7476
Succinyl-CoA:acetate CoA-transferase	B3EY95	SCACT_ACEAC	Acetobacter aceti	3	0.7449
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7442
RNA-directed RNA polymerase	P11124	RDRP_BPPH6	Pseudomonas phage phi6	3	0.7399
Tyrosine-protein kinase Lck	P06239	LCK_HUMAN	Homo sapiens	4	0.7392
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	4	0.7332
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7306
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7304
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7302
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7293
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7290
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7287
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7277
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7276
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7273
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7260
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7257
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7253
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7238
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7229
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7227
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7225
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7220
Copper-transporting ATPase	Q97UU7	Q97UU7_SACS2	Saccharolobus solfataricus	4	0.7216
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7206
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7189
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7187
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7187
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7184
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7182
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7180
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7172
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7164
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	2	0.7149
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7127
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7125
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7118
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7116
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7115
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7114
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	4	0.7113
Pantothenate kinase	P9WPA7	COAA_MYCTU	Mycobacterium tuberculosis	4	0.7108
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7105
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7101
Eukaryotic translation initiation factor 4E	P06730	IF4E_HUMAN	Homo sapiens	5	0.7096
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7091
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7088
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7088
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	2	0.7080
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7074
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7072
Tryptophan--tRNA ligase	Q9PIB4	SYW_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	4	0.7053
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7050
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7044
Ribosomal RNA small subunit methyltransferase NEP1	Q06287	NEP1_YEAST	Saccharomyces cerevisiae	4	0.7039
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7024
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7020
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7019
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7018
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7018
NTPase P4	Q94M05	Q94M05_9VIRU	Pseudomonas phage phi12	3	0.7009
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7007
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7006
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7000
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7000

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