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5-p-cis-coumaroylquinic acid

Family: Plantae - Zygophyllaceae
Kingdom: Plantae
Class: Phenolic
- Subclass: Quinic Acid Derivative

Canonical Smiles	O=C(O[C@@H]1C[C@@](O)(C[C@H]([C@H]1O)O)C(=O)O)/C=C\c1ccc(cc1)O
InChI	InChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(19)24-12-8-16(23,15(21)22)7-11(18)14(12)20/h1-6,11-12,14,17-18,20,23H,7-8H2,(H,21,22)/b6-3-/t11-,12-,14-,16+/m1/s1
InChIKey	BMRSEYFENKXDIS-JMYXGHFSSA-N
Formula	C₁₆H₁₈O₈
HBA	7
HBD	5
MW	338.31
Rotatable Bonds	4
TPSA	144.52
LogP	-0.35
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	338.1
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Tribulus terrestris	Zygophyllaceae	Plantae	210369

Showing of synonyms

Hammoda HM, Ghazy NM, et al. (2013). Chemical constituents from Tribulus terrestris and screening of their antioxidant activity. Phytochemistry,2013,92,153-159. [View] [PubMed]

Pubchem: 90478782

Cas: 185502-68-5

Zinc: ZINC000013514678

Nmrshiftdb2: 60028583

No compound-protein relationship available.

SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 338.31 g/mol

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 338.31 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 338.31 g/mol

Antioxidant

Absorption

Caco-2 (logPapp): -6.31
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -3.7
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.82

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.74
Plasma Protein Binding: 60.21
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: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.83
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.99
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.64
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 3.76
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: -2.07
Rat (Acute): 1.99
Rat (Chronic Oral): 3.09
Fathead Minnow: 3.83
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 416.54
Hydration Free Energy: -10.32
Log(D) at pH=7.4: -1.19
Log(P): -0.08
Log S: -1.51
Log(Vapor Pressure): -12.64
Melting Point: 194.78
pKa Acid: 2.98
pKa Basic: 6.63

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8953
Flavin-dependent monooxygenase	Q93L51	TETX_BACT4	Bacteroides thetaiotaomicron	3	0.8953
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8917
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.8917
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8912
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.8912
Ectonucleoside triphosphate diphosphohydrolase I	Q5ZUA2	Q5ZUA2_LEGPH	Legionella pneumophila subsp. pneumophila	3	0.8807
Ectonucleoside triphosphate diphosphohydrolase I	Q5ZUA2	Q5ZUA2_LEGPH	Legionella pneumophila subsp. pneumophila	3	0.8807
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8649
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8649
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8545
ATP-dependent molecular chaperone HSP82	P02829	HSP82_YEAST	Saccharomyces cerevisiae	3	0.8545
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.8468
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.8468
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8372
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.8372
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8310
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8310
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8310
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8310
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8262
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.8262
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8260
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8260
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8205
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8205
Shikimate dehydrogenase (NADP(+))	P56119	AROE_HELPY	Helicobacter pylori	3	0.8122
Shikimate dehydrogenase (NADP(+))	P56119	AROE_HELPY	Helicobacter pylori	3	0.8122
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7927
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7927
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7911
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7911
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7910
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7910
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7771
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	3	0.7771
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7649
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7649
Nodulation fucosyltransferase NodZ	Q9AQ17	Q9AQ17_BRASW	Bradyrhizobium sp	3	0.7608
Nodulation fucosyltransferase NodZ	Q9AQ17	Q9AQ17_BRASW	Bradyrhizobium sp	3	0.7608
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7571
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7571
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7567
Thermolysin	P00800	THER_BACTH	Bacillus thermoproteolyticus	3	0.7567
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7537
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7537
Precorrin-3 methylase	O68097	O68097_RHOCA	Rhodobacter capsulatus	3	0.7519
Precorrin-3 methylase	O68097	O68097_RHOCA	Rhodobacter capsulatus	3	0.7519
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7508
Cyclin-dependent kinase 9	P50750	CDK9_HUMAN	Homo sapiens	3	0.7508
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	2	0.7495
Streptavidin	P22629	SAV_STRAV	Streptomyces avidinii	2	0.7495
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7475
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7475
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7399
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7399
Ribosome-inactivating protein alpha-trichosanthin	P09989	RIPT_TRIKI	Trichosanthes kirilowii	3	0.7396
Ribosome-inactivating protein alpha-trichosanthin	P09989	RIPT_TRIKI	Trichosanthes kirilowii	3	0.7396
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7372
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.7372
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7362
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	4	0.7362
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7337
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7337
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7333
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7333
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7326
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7326
Integrin alpha-5	P08648	ITA5_HUMAN	Homo sapiens	3	0.7302
Integrin alpha-5	P08648	ITA5_HUMAN	Homo sapiens	3	0.7302
Carboxyethyl-arginine beta-lactam-synthase	P0DJQ7	BLS_STRCL	Streptomyces clavuligerus	3	0.7297
Carboxyethyl-arginine beta-lactam-synthase	P0DJQ7	BLS_STRCL	Streptomyces clavuligerus	3	0.7297
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	3	0.7296
Virulence sensor histidine kinase PhoQ	P0DM80	PHOQ_SALTY	Salmonella typhimurium	3	0.7296
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7285
Ras-related protein Ral-B	P11234	RALB_HUMAN	Homo sapiens	3	0.7285
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7255
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7255
Cytosol aminopeptidase	P00727	AMPL_BOVIN	Bos taurus	2	0.7252
Cytosol aminopeptidase	P00727	AMPL_BOVIN	Bos taurus	2	0.7252
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7248
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7248
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7241
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7241
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7240
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	3	0.7240
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7235
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7235
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	3	0.7217
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	3	0.7217
Acetyl-CoA acetyltransferase, mitochondrial	P24752	THIL_HUMAN	Homo sapiens	3	0.7216
Acetyl-CoA acetyltransferase, mitochondrial	P24752	THIL_HUMAN	Homo sapiens	3	0.7216
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7212
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7212
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7201
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7201
23S rRNA (guanine(745)-N(1))-methyltransferase	P36999	RLMA_ECOLI	Escherichia coli	3	0.7197
23S rRNA (guanine(745)-N(1))-methyltransferase	P36999	RLMA_ECOLI	Escherichia coli	3	0.7197
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7196
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7196
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7190
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7190
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7189
Caffeoyl-CoA O-methyltransferase	Q40313	CAMT_MEDSA	Medicago sativa	3	0.7189
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7179
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	3	0.7179
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	2	0.7176
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	2	0.7176
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7170
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7170
Methionine--tRNA ligase	P00959	SYM_ECOLI	Escherichia coli	3	0.7170
Methionine--tRNA ligase	P00959	SYM_ECOLI	Escherichia coli	3	0.7170
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7157
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7157
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7154
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7154
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7138
Aurora kinase A	O14965	AURKA_HUMAN	Homo sapiens	3	0.7138
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7137
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7137
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7137
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7137
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7117
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7117
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7100
Coagulation factor X	P00742	FA10_HUMAN	Homo sapiens	2	0.7100
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7100
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7100
2'-5'-oligoadenylate synthase 1	P00973	OAS1_HUMAN	Homo sapiens	2	0.7093
2'-5'-oligoadenylate synthase 1	P00973	OAS1_HUMAN	Homo sapiens	2	0.7093
Hydroxymethylglutaryl-CoA synthase	Q9FD71	HMGCS_ENTFL	Enterococcus faecalis	2	0.7082
Hydroxymethylglutaryl-CoA synthase	Q9FD71	HMGCS_ENTFL	Enterococcus faecalis	2	0.7082
Holliday junction branch migration complex subunit RuvB	Q9PMT7	RUVB_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	2	0.7077
Holliday junction branch migration complex subunit RuvB	Q9PMT7	RUVB_CAMJE	Campylobacter jejuni subsp. jejuni serotype O:2	2	0.7077
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7075
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7075
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1	Q9Y3Z3	SAMH1_HUMAN	Homo sapiens	3	0.7066
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1	Q9Y3Z3	SAMH1_HUMAN	Homo sapiens	3	0.7066
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7063
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7063
Malate dehydrogenase	P10584	MDH_THETH	Thermus thermophilus	3	0.7054
Malate dehydrogenase	P10584	MDH_THETH	Thermus thermophilus	3	0.7054
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7049
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7049
Cytosol aminopeptidase	O86436	AMPA_PSEPU	Pseudomonas putida	3	0.7041
Cytosol aminopeptidase	O86436	AMPA_PSEPU	Pseudomonas putida	3	0.7041
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7038
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7038
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7033
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7033
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	3	0.7032
Nucleoside 2-deoxyribosyltransferase	Q8RLY5	Q8RLY5_LACHE	Lactobacillus helveticus	3	0.7032
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7031
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7031
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7023
3-hydroxy-3-methylglutaryl-coenzyme A reductase	P04035	HMDH_HUMAN	Homo sapiens	3	0.7023
Chaperone protein ClpB	Q9RA63	CLPB_THET8	Thermus thermophilus	4	0.7005
Chaperone protein ClpB	Q9RA63	CLPB_THET8	Thermus thermophilus	4	0.7005
Lipoprotein E	P26093	HEL_HAEIN	Haemophilus influenzae	3	0.7001
Lipoprotein E	P26093	HEL_HAEIN	Haemophilus influenzae	3	0.7001

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