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(Z)-p-coumaric acid

Family: Plantae - Hypericaceae
Kingdom: Plantae
Class: Phenolic

Canonical Smiles	OC(=O)/C=C\c1ccc(cc1)O
InChI	InChI=1S/C9H8O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-6,10H,(H,11,12)/b6-3-
InChIKey	NGSWKAQJJWESNS-UTCJRWHESA-N
Formula	C₉H₈O₃
HBA	2
HBD	2
MW	164.16
Rotatable Bonds	2
TPSA	57.53
LogP	1.49
Number Rings	1
Number Aromatic Rings	1
Heavy Atom Count	12
Formal Charge	0
Fraction CSP3	0.0
Exact Mass	164.05
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Euphorbia gaditana	Euphorbiaceae	Plantae	3990
2	Hypericum sinaicum	Hypericaceae	Plantae	1137027

Showing of synonyms

El-Hawary S, Ahmed FA, et al. (2022). Antiinflammatory and antioxidant activity of Hypericum sinaicum Boiss. growing widely in Egypt. Natural product research, 2022, 36(11), 2913-2916. [View] [PubMed]
Badaoui M, Magid A, et al. (2020). Antioxidant activity-guided isolation of constituents from Euphorbia gaditana Coss. and their antioxidant and tyrosinase inhibitory activities. Phytochemistry Letters, 2020, 39, 99-104. [View]

Pubchem: 1549106

Cas: 4501-31-9

Zinc: ZINC000004632590

Kegg Ligand: C06738

Chebi: 17450

Nmrshiftdb2: 60025266

Metabolights: MTBLC17450

Chembl: CHEMBL2336752

CPRiL: 410708

SMILES: c1ccccc1

Level: 0

Mol. Weight: 164.16 g/mol

Antioxidant

Absorption

Caco-2 (logPapp): -4.87
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.11
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.74

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.76
Plasma Protein Binding: 43.12
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: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 5.48
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -0.09
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 0.92
Liver Injury II: Safe
hERG Blockers: Safe
Daphnia Maga: 4.01
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: 0.74
Rat (Acute): 1.83
Rat (Chronic Oral): 2.52
Fathead Minnow: 3.98
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: 325.04
Hydration Free Energy: -9.31
Log(D) at pH=7.4: -1.41
Log(P): 1.96
Log S: -2.25
Log(Vapor Pressure): -5.44
Melting Point: 238.19
pKa Acid: 4.49
pKa Basic: 2.29

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.9464
Anthranilate phosphoribosyltransferase	P9WFX5	TRPD_MYCTU	Mycobacterium tuberculosis	3	0.9419
Polymerase acidic protein	Q5EP34	Q5EP34_9INFA	Influenza A virus	3	0.9387
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9336
Threonine synthase 1, chloroplastic	Q9S7B5	THRC1_ARATH	Arabidopsis thaliana	3	0.9235
2-methyl-3-hydroxypyridine-5-carboxylic acid oxygenase	Q988D3	Q988D3_RHILO	Mesorhizobium japonicum)	3	0.9227
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.9067
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.8983
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.8908
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8817
Carboxyethyl-arginine beta-lactam-synthase	P0DJQ7	BLS_STRCL	Streptomyces clavuligerus	3	0.8713
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	3	0.8680
Trichothecene 15-O-acetyltransferase TRI3	Q9C1B7	TRI3_FUSSP	Fusarium sporotrichioides	3	0.8500
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.8353
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	3	0.8322
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8296
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8253
Prenyltransferase	Q4R2T2	Q4R2T2_STRC1	Streptomyces sp	3	0.8215
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8205
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8203
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.8141
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	3	0.8123
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.8044
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7988
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7984
NADPH-dependent 7-cyano-7-deazaguanine reductase	Q9KTK0	QUEF_VIBCH	Vibrio cholerae serotype O1	3	0.7967
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase	Q9TQS6	DHDH_MACFA	Macaca fascicularis	3	0.7935
Cyclic nucleotide-gated potassium channel mll3241	Q98GN8	CNGK1_RHILO	Mesorhizobium japonicum)	3	0.7927
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7914
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7893
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2	O88703	HCN2_MOUSE	Mus musculus	3	0.7815
cAMP-activated global transcriptional regulator Vfr	P55222	VFR_PSEAE	Pseudomonas aeruginosa	3	0.7798
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7791
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7790
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7754
Precorrin-3 methylase	O68097	O68097_RHOCA	Rhodobacter capsulatus	3	0.7747
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7724
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7708
Mevalonate kinase	P17256	KIME_RAT	Rattus norvegicus	3	0.7696
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	3	0.7692
5'-methylthioadenosine nucleosidase	Q9T0I8	MTN1_ARATH	Arabidopsis thaliana	3	0.7691
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 1	O88704	HCN1_MOUSE	Mus musculus	3	0.7687
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7669
HD domain protein	Q836G9	Q836G9_ENTFA	Enterococcus faecalis	3	0.7642
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7636
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	3	0.7619
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7588
Myosin heavy chain, striated muscle	P24733	MYS_ARGIR	Argopecten irradians	3	0.7585
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7549
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7543
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2	Q9UL51	HCN2_HUMAN	Homo sapiens	3	0.7539
cGMP-dependent protein kinase 2	Q13237	KGP2_HUMAN	Homo sapiens	2	0.7530
Methylmalonyl-CoA decarboxylase	P52045	SCPB_ECOLI	Escherichia coli	3	0.7523
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7517
Cyclic nucleotide-binding domain-containing protein	E0RR11	E0RR11_SPITD	Spirochaeta thermophila	3	0.7512
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	3	0.7495
tRNA (cytidine-2'-O-)-methyltransferase TrmJ	Q4JB16	TRMJ_SULAC	Sulfolobus acidocaldarius	3	0.7473
Genome polyprotein	Q8QL64	Q8QL64_9FLAV	Modoc virus	3	0.7445
Serine/threonine-protein kinase PLK1	P53350	PLK1_HUMAN	Homo sapiens	3	0.7434
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2	O88703	HCN2_MOUSE	Mus musculus	2	0.7431
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7430
Formylmethanofuran--tetrahydromethanopterin formyltransferase	Q49610	FTR_METKA	Methanopyrus kandleri	3	0.7415
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7415
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	2	0.7413
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7380
Tyrosine-protein kinase SYK	P43405	KSYK_HUMAN	Homo sapiens	3	0.7355
Caffeic acid O-methyltransferase	Q9ZTU2	Q9ZTU2_LOLPR	Lolium perenne	3	0.7348
Ras-related protein Rap-1b	P61224	RAP1B_HUMAN	Homo sapiens	3	0.7344
Genome polyprotein	A9LIE0	A9LIE0_9FLAV	dengue virus type 3	3	0.7342
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7336
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7326
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7311
Nitric oxide synthase 1	P29476	NOS1_RAT	Rattus norvegicus	3	0.7308
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	2	0.7305
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7286
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7279
Purine nucleoside phosphorylase DeoD-type	P0ABP9	DEOD_ECO57	Escherichia coli O157:H7	2	0.7279
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7272
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7260
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7257
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7251
Genome polyprotein	Q6YMS4	POLG_DEN3S	Dengue virus type 3	3	0.7249
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	3	0.7242
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	2	0.7240
Pyridoxal kinase	O00764	PDXK_HUMAN	Homo sapiens	2	0.7239
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7231
Petrobactin biosynthesis protein AsbB	Q81RQ8	Q81RQ8_BACAN	Bacillus anthracis	3	0.7226
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7220
Angiotensin-converting enzyme	Q10714	ACE_DROME	Drosophila melanogaster	2	0.7218
Purine nucleoside phosphorylase DeoD-type	Q5EEL8	DEOD_BACCE	Bacillus cereus	2	0.7215
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	2	0.7208
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7204
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7192
histidine kinase	Q9WZV7	Q9WZV7_THEMA	Thermotoga maritima	3	0.7182
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7174
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7170
Avidin	P02701	AVID_CHICK	Gallus gallus	2	0.7163
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	3	0.7151
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7150
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7149
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7143
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	3	0.7141
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	2	0.7139
Aspartate carbamoyltransferase catalytic subunit	P0A786	PYRB_ECOLI	Escherichia coli	2	0.7132
DNA-binding transcriptional dual regulator CRP	P0ACJ8	CRP_ECOLI	Escherichia coli	2	0.7131
S-methyl-5'-thioadenosine phosphorylase	I0B503	I0B503_SCHMA	Schistosoma mansoni	3	0.7128
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7124
AcsD	Q93AT8	Q93AT8_DICCH	Dickeya chrysanthemi	3	0.7124
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7123
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7122
Uncharacterized protein YML079W	Q03629	YMH9_YEAST	Saccharomyces cerevisiae	2	0.7106
L-lactate dehydrogenase	Q27743	LDH_PLAFD	Plasmodium falciparum	2	0.7099
Gentisate 1,2-dioxygenase	Q67FT0	Q67FT0_PSESE	Pseudaminobacter salicylatoxidans	2	0.7086
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7082
Biflaviolin synthase CYP158A1	Q9KZF5	C1581_STRCO	Streptomyces coelicolor / M145)	2	0.7080
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	2	0.7078
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2	O88703	HCN2_MOUSE	Mus musculus	2	0.7074
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7068
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7065
Three-prime repair exonuclease 1	Q91XB0	TREX1_MOUSE	Mus musculus	2	0.7060
Single-stranded-DNA-specific exonuclease RecJ	D0EM60	D0EM60_DEIRD	Deinococcus radiodurans	2	0.7056
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	2	0.7054
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7054
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7053
2',3'-cyclic-nucleotide 3'-phosphodiesterase	P16330	CN37_MOUSE	Mus musculus	2	0.7051
5-methylthioadenosine/S-adenosylhomocysteine deaminase	Q7NZ90	Q7NZ90_CHRVO	Chromobacterium violaceum	2	0.7051
N-terminal acetyltransferase A complex subunit NAT1	P12945	NAT1_YEAST	Saccharomyces cerevisiae	2	0.7048
Purine nucleoside phosphorylase	P00491	PNPH_HUMAN	Homo sapiens	2	0.7045
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7043
Egl nine homolog 1	Q9GZT9	EGLN1_HUMAN	Homo sapiens	2	0.7041
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7033
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	2	0.7032
Protocatechuate 3,4-dioxygenase beta chain	P00437	PCXB_PSEPU	Pseudomonas putida	2	0.7030
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7030
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7020
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7016
Cyclic AMP receptor protein	Q5SID7	CRP_THET8	Thermus thermophilus	2	0.7015
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7014

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