ANPDB

Select a section from the left sidebar

Dicaffeoylquinic acid

Family: Plantae - Convolvulaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Polyphenolic

Canonical Smiles	O=C(OC1[C@H](O)CC(C[C@H]1O)(OC(=O)/C=C/c1ccc(c(c1)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(32)36-23-19(30)11-25(24(34)35,12-20(23)31)37-22(33)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-31H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23?,25?/m1/s1
InChIKey	IYXQRCXQQWUFQV-RDJMKVHDSA-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	Convolvulus althaeoides	Convolvulaceae	Plantae	267570

Showing of synonyms

Hrichi S, Chaabane-Banaoues R, et al. (2020). Effect of seasonal variation on the chemical composition and antioxidant and antifungal activities of Convolvulus althaeoides L. leaf extract. Arabian Journal of Chemistry, 2020, 13(6), 5651-5668. [View]

Pubchem: 12358846

Cas: 251320-68-0

Gnps: CCMSLIB00010012012

Zinc: ZINC000013597248

Chebi: 176204

Nmrshiftdb2: 60028435

CPRiL: 60122

SMILES: c1ccccc1C=CC(=O)OC2CCC(CC2)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): -6.7
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -5.21
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.08

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.87
Plasma Protein Binding: 70.72
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: 9.41
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.36
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.66
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.5
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: -460.15
Rat (Acute): 2.16
Rat (Chronic Oral): 3.52
Fathead Minnow: 3.92
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Toxic
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 578.33
Hydration Free Energy: -2.79
Log(D) at pH=7.4: -0.08
Log(P): 1.24
Log S: -2.44
Log(Vapor Pressure): -14.52
Melting Point: 228.07
pKa Acid: 5.07
pKa Basic: 5.62

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	0.9349
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.9253
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.9145
MAP kinase-activated protein kinase 2	P49137	MAPK2_HUMAN	Homo sapiens	3	0.9056
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.9036
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8831
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8777
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8684
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8616
Avidin	P02701	AVID_CHICK	Gallus gallus	3	0.8469
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	4	0.8382
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.8362
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8358
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8346
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	3	0.8311
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8306
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8290
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8289
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.8229
S-adenosylmethionine decarboxylase proenzyme	P17707	DCAM_HUMAN	Homo sapiens	3	0.8216
Aminoglycoside N(3)-acetyltransferase	A0A3P1UCA6	Q81P86_BACAN	Bacillus anthracis	3	0.8197
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8170
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8166
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8162
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.8158
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.8132
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.8080
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8013
Multidrug efflux pump subunit AcrB	P31224	ACRB_ECOLI	Escherichia coli	4	0.7984
Valacyclovir hydrolase	Q86WA6	BPHL_HUMAN	Homo sapiens	3	0.7946
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7943
Lysozyme C II	P11941	LYSC2_ONCMY	Oncorhynchus mykiss	3	0.7883
Beta-1 adrenergic receptor	P07700	ADRB1_MELGA	Meleagris gallopavo	3	0.7860
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7824
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7806
5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase	Q8U0R7	PURP_PYRFU	Pyrococcus furiosus	3	0.7750
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7750
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7746
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7703
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	3	0.7698
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7683
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7673
Tubulin--tyrosine ligase	F6Z895	A9ULH4_XENTR	Xenopus tropicalis	4	0.7661
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7565
cAMP-dependent protein kinase catalytic subunit alpha	P00517	KAPCA_BOVIN	Bos taurus	3	0.7563
Tyrosine-protein kinase JAK3	P52333	JAK3_HUMAN	Homo sapiens	3	0.7560
Riboflavin biosynthesis protein	Q9WZW1	Q9WZW1_THEMA	Thermotoga maritima	4	0.7539
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	3	0.7526
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7499
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7498
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.7484
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7482
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7451
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7442
Genome polyprotein	A0EKU1	A0EKU1_9FLAV	Meaban virus	3	0.7436
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7429
Threonine--tRNA ligase	P0A8M3	SYT_ECOLI	Escherichia coli	3	0.7394
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7390
Purine nucleoside phosphorylase	Q8I3X4	Q8I3X4_PLAF7	Plasmodium falciparum	3	0.7375
Tyrosine-protein kinase JAK1	P23458	JAK1_HUMAN	Homo sapiens	3	0.7366
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7354
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7353
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7329
Eukaryotic translation initiation factor 4E type 2	O60573	IF4E2_HUMAN	Homo sapiens	4	0.7289
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7287
Hydroxymethylglutaryl-CoA synthase	Q9FD71	HMGCS_ENTFL	Enterococcus faecalis	2	0.7283
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7277
APH(2'')-Id	O68183	O68183_ENTCA	Enterococcus casseliflavus	3	0.7269
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7268
Probable enoyl-CoA hydratase EchA8	P9WNN9	ECHA8_MYCTU	Mycobacterium tuberculosis	4	0.7265
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7251
DNA translocase FtsK	Q9I0M3	FTSK_PSEAE	Pseudomonas aeruginosa	3	0.7250
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7246
non-specific serine/threonine protein kinase	Q6FS46	Q6FS46_CANGA	Candida glabrata	4	0.7232
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.7231
Serine/threonine-protein kinase N1	Q16512	PKN1_HUMAN	Homo sapiens	3	0.7229
Uncharacterized protein	Q8DY32	Q8DY32_STRA5	Streptococcus agalactiae serotype V	4	0.7227
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7226
Histone-lysine N-methyltransferase SETD7	Q8WTS6	SETD7_HUMAN	Homo sapiens	3	0.7223
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	4	0.7197
Inosine-5'-monophosphate dehydrogenase	P50097	IMDH_TRIFO	Tritrichomonas foetus	3	0.7189
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7186
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7179
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7175
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7171
Ribosomal RNA small subunit methyltransferase NEP1	Q06287	NEP1_YEAST	Saccharomyces cerevisiae	4	0.7167
histidine kinase	O32393	O32393_ARTPT	Arthrospira platensis	3	0.7165
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7149
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7148
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	3	0.7144
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7134
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	2	0.7130
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7129
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7127
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7126
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7121
Protein mono-ADP-ribosyltransferase PARP3	Q9Y6F1	PARP3_HUMAN	Homo sapiens	3	0.7114
Deoxycytidine kinase	P27707	DCK_HUMAN	Homo sapiens	3	0.7113
Activated CDC42 kinase 1	Q07912	ACK1_HUMAN	Homo sapiens	3	0.7102
DNA (cytosine-5)-methyltransferase 3A	O88508	DNM3A_MOUSE	Mus musculus	3	0.7099
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	4	0.7098
Flagellum-specific ATP synthase	P26465	FLII_SALTY	Salmonella typhimurium	2	0.7098
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7093
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7090
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7089
Nonspecific lipid-transfer protein, putative	C9ZUV7	C9ZUV7_TRYB9	Trypanosoma brucei gambiense	3	0.7085
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7077
Bifunctional AAC/APH	P0A0C1	AACA_STAAU	Staphylococcus aureus	4	0.7076
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7073
Eukaryotic translation initiation factor 4E-1	P29557	IF4E1_WHEAT	Triticum aestivum	4	0.7072
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4	Q8GZB6	SUVH4_ARATH	Arabidopsis thaliana	3	0.7071
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	2	0.7068
mRNA cap guanine-N7 methyltransferase	Q8SR66	MCES_ENCCU	Encephalitozoon cuniculi	4	0.7063
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7063
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic	Q43088	RBCMT_PEA	Pisum sativum	3	0.7061
Nucleoside diphosphate kinase A 2	P52175	NDKA2_BOVIN	Bos taurus	4	0.7055
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	3	0.7055
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	2	0.7054
DNA ligase	P43813	DNLJ_HAEIN	Haemophilus influenzae	3	0.7051
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7048
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7042
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7042
Histone-lysine N-methyltransferase EHMT1	Q9H9B1	EHMT1_HUMAN	Homo sapiens	3	0.7038
Histone-lysine N-methyltransferase EHMT2	Q96KQ7	EHMT2_HUMAN	Homo sapiens	3	0.7037
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7031
Chorismate mutase AroH	P19080	AROH_BACSU	Bacillus subtilis	2	0.7031
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7028
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7027
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7023
Vitamin D-binding protein	P02774	VTDB_HUMAN	Homo sapiens	2	0.7016
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7015
Probable bifunctional SAT/APS kinase	O67174	SATC_AQUAE	Aquifex aeolicus	3	0.7006
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7004

Download SDF