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4,5-dicaffeoyl quinic acid

Family: Plantae - Convolvulaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Hydroxycinnamic Acid

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-ZSGFIFMUSA-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	Plantae	91244
2	Helichrysum mechowianum	Compositae	Plantae	3030040
3	Cressa cretica	Convolvulaceae	Plantae	1465651

Showing of synonyms

Abdallah H.M.I, Elshamy A.I, et al. (2017). Anti-inflammatory, Antipyretic, and Antinociceptive Effects of a Cressa cretica Aqueous Extract. Planta medica, 2017, 83(17), 1313-1320. [View] [PubMed]
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]
Malolo FA, Bissoue Nouga A, et al. (2015). Protease-inhibiting, molecular modeling and antimicrobial activities of extracts and constituents from Helichrysum foetidum and Helichrysum mechowianum (compositae).. Chemistry Central journal,2015, 9, 32. [View] [PubMed]

Pubchem: 13887346

Zinc: ZINC000038194827

Nmrshiftdb2: 80002976

Chembl: CHEMBL453276

CPRiL: 117991

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): -6.82
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: 80.25
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: -1.95
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: -455.61
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: 586.32
Hydration Free Energy: -3.12
Log(D) at pH=7.4: 0.06
Log(P): 1.45
Log S: -2.81
Log(Vapor Pressure): -15.08
Melting Point: 258.55
pKa Acid: 5.08
pKa Basic: 5.9

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	0.9366
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9147
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9060
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.8863
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	3	0.8809
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8761
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.8708
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8685
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	3	0.8648
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8498
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.8494
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8479
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.8441
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8438
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8434
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8345
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8315
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8300
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8278
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	3	0.8232
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.8229
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.8213
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.8150
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8066
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7975
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7962
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7921
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7910
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.7819
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7804
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7802
Ectonucleoside triphosphate diphosphohydrolase I	Q5ZUA2	Q5ZUA2_LEGPH	Legionella pneumophila subsp. pneumophila	3	0.7775
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7747
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7739
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7731
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7724
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7710
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7675
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	5	0.7659
Seminal ribonuclease	P00669	RNS_BOVIN	Bos taurus	3	0.7633
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7633
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7627
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7600
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7599
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7591
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7575
Succinyl-CoA:acetate CoA-transferase	B3EY95	SCACT_ACEAC	Acetobacter aceti	3	0.7567
Inosine-5'-monophosphate dehydrogenase	P50097	IMDH_TRIFO	Tritrichomonas foetus	3	0.7528
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7506
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7502
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7501
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7496
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7474
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.7468
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7435
Nucleoside diphosphate kinase	Q2SWE7	NDK_BURTA	Burkholderia thailandensis	3	0.7431
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7404
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7345
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7283
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7278
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7278
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7275
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7268
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7259
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7257
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7251
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase	P12995	BIOA_ECOLI	Escherichia coli	3	0.7248
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7223
Hydroxymethylglutaryl-CoA synthase	Q9FD71	HMGCS_ENTFL	Enterococcus faecalis	2	0.7199
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7193
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7188
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7186
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7172
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7165
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7151
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7148
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7140
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7137
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7134
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7123
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7122
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7113
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7111
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	3	0.7101
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7093
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7092
mRNA-capping enzyme subunit alpha	P78587	MCE1_CANAX	Candida albicans	3	0.7091
Histone-lysine N-methyltransferase 2C	Q8NEZ4	KMT2C_HUMAN	Homo sapiens	3	0.7088
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7088
Histone-lysine N-methyltransferase EHMT2	Q96KQ7	EHMT2_HUMAN	Homo sapiens	3	0.7070
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7065
ADP compounds hydrolase NudE	P45799	NUDE_ECOLI	Escherichia coli	2	0.7065
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7062
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7051
Tyrosine-protein kinase ABL1	P00519	ABL1_HUMAN	Homo sapiens	3	0.7049
Insulin-degrading enzyme	P14735	IDE_HUMAN	Homo sapiens	3	0.7049
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7046
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7041
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	4	0.7034
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7029
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7018
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7017
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7016
Alpha-ketoglutarate-dependent dioxygenase FTO	Q9C0B1	FTO_HUMAN	Homo sapiens	2	0.7016
L-lactate dehydrogenase	Q5SJA1	LDH_THET8	Thermus thermophilus	3	0.7011

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