Caffeic acid - Compound Card

Caffeic acid

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Caffeic acid

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae, Animalia
  • Class: Phenolic
    • Subclass: Hydroxycinnamic Acid
Canonical Smiles OC(=O)/C=C/c1ccc(c(c1)O)O
InChI InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
InChIKey QAIPRVGONGVQAS-DUXPYHPUSA-N
Formula C9H8O4
HBA 3
HBD 3
MW 180.16
Rotatable Bonds 2
TPSA 77.76
LogP 1.2
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 13
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 180.04
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Thalassia hemprichii Hydrocharitaceae Plantae 55496
2 Apis mellifica Apidae Animalia 7460
3 Cotoneaster orbicularis Rosaceae Plantae 1851000
4 Ferula lutea Apiaceae Plantae 52470
5 Coriandrum sativum Apiaceae Plantae 4047
6 Cynara scolymus Asteraceae Plantae 59895
7 Sphaeranthus bullatus Asteraceae Plantae 1548657
8 Vepris glomerata Rutaceae Plantae 2695416
9 Vepris glomerata Rutaceae Plantae 2695416
10 Achyranthes aspera Amaranthaceae Plantae 240005
11 Rosmarinuseriocalyx Lamiaceae Plantae

Showing of synonyms

  • Hawas UW (2014). A new 8-hydroxy flavone o-xyloside sulfate and antibacterial activity from the Egyptian seagrass Thalassia hemprichii. Chemistry of Natural Compounds,2014,50(4),546-548. [View]
  • Kiplimo JJ, Koorbanally NA. (2012). Antibacterial activity of an epoxidised prenylated cinnamaldehdye derivative from Vepris glomerata. Phytochemistry Letters,2012,5(3),438-442. [View] [PubMed]
  • Ndhlala AR, Ghebrehiwot HM, et al. (2015). Antimicrobial, anthelmintic activities and characterisation of functional phenolic acids of Achyranthes aspera linn.: a medicinal plant used for the treatment of wounds and Ringworm in East Africa.. Frontiers in pharmacology,2015,6,274. [View] [PubMed]
  • Msaada K, Ben Jemia M, et al. (2014). Antioxidant activity of methanolic extracts from three coriander (Coriandrum sativum L.) fruit varieties. Arabian Journal of Chemistry,2014, in press. [View]
  • Machumi F, Yenesew A, et al. (2012). Antiparasitic and anticancer carvotacetone derivatives of Sphaeranthus bullatus. Natural Product Communications,2012,7(9),1123-1126. [View] [PubMed]
  • Boufadi YM, Soubhye J, et al. (2014). Characterization and antioxidant properties of six Algerian propolis extracts: ethyl acetate extracts inhibit myeloperoxidase activity. International Journal of Molecular Sciences,2014,15(2),2327-2345. [View] [PubMed]
  • Hammouda FM, Seif El-Nesr MM, et al. (1991). HPLC evaluation of the active constituents in the newly introduced romanian strain of Cynara scolymus cultivated in Egypt. Planta Medica,1991,57(2),A119-A120. [View]
  • Ben Salem S, Jabrane A, et al. (2013). New bioactive dihydrofuranocoumarins from the roots of the Tunisian Ferula lutea (Poir.) Maire.. Bioorganic and Medicinal Chemistry Letters,2013,23(14),4248-4252. [View] [PubMed]
  • Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]
  • Kiplimo JJ, Koorbanally NA. (2012). The phytochemistry and biological activity of secondary metabolites from Kenyan Vernonia and Vepris species. PhD Thesis, University of Kwazulu-Natal, South Africa,2012. [View] [PubMed]
  • El-Mousallamy AM, Hussein SA, et al. (2000). Unusual phenolic glycosides from Cotoneaster orbicularis. Phytochemistry,2000,53(6),699-704. [View] [PubMed]
Pubchem: 689043
Kegg Ligand: C01197
Chebi: 16433
Nmrshiftdb2: 20039649
Metabolights: MTBLC16433
Chembl: CHEMBL145
Drugbank: DB01880
Pdb Ligand: DHC
Bindingdb: 4375
CPRiL: 6346
Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 180.16 g/mol

Antimicrobial
Antioxidant
Cytotoxic

Absorption

Caco-2 (logPapp)
-4.95
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.39
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.7
Plasma Protein Binding
31.07
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
9.38
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.15
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.27
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.47
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
3.11
Rat (Acute)
1.78
Rat (Chronic Oral)
2.91
Fathead Minnow
4.01
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
356.62
Hydration Free Energy
-11.66
Log(D) at pH=7.4
-1.56
Log(P)
1.46
Log S
-1.63
Log(Vapor Pressure)
-6.19
Melting Point
228.17
pKa Acid
5.49
pKa Basic
4.68
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 0.9321
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9321
Feruloyl esterase A O42807 FAEA_ASPNG Aspergillus niger 3 0.9138
Feruloyl esterase A O42807 FAEA_ASPNG Aspergillus niger 3 0.9138
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 3 0.9112
Adenosylmethionine-8-amino-7-oxononanoate aminotransferase P12995 BIOA_ECOLI Escherichia coli 3 0.9112
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9106
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9106
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9029
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9029
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 4 0.9002
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 4 0.9002
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8992
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8992
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.8973
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.8973
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8639
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.8639
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8499
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8499
Caffeic acid 3-O-methyltransferase P28002 COMT1_MEDSA Medicago sativa 3 0.8449
Caffeic acid 3-O-methyltransferase P28002 COMT1_MEDSA Medicago sativa 3 0.8449
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8431
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8431
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8360
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8360
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8258
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8258
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8248
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8248
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8190
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8190
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 4 0.8128
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 4 0.8128
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.8122
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.8122
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8055
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8055
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8051
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.8051
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7980
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7980
CalS13 Q8KND8 Q8KND8_MICEC Micromonospora echinospora 4 0.7961
CalS13 Q8KND8 Q8KND8_MICEC Micromonospora echinospora 4 0.7961
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7909
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7909
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7844
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7844
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7778
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7778
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7751
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7751
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7653
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7653
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7576
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7576
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7487
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7487
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7454
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7454
Malate synthase G P9WK17 MASZ_MYCTU Mycobacterium tuberculosis 3 0.7442
Malate synthase G P9WK17 MASZ_MYCTU Mycobacterium tuberculosis 3 0.7442
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7438
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7438
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 4 0.7436
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 4 0.7436
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7422
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7422
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7368
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7368
Aspartate aminotransferase P00509 AAT_ECOLI Escherichia coli 3 0.7350
Aspartate aminotransferase P00509 AAT_ECOLI Escherichia coli 3 0.7350
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7295
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7295
Ribosomal RNA small subunit methyltransferase Nep1 Q57977 NEP1_METJA Methanocaldococcus jannaschii 3 0.7291
Ribosomal RNA small subunit methyltransferase Nep1 Q57977 NEP1_METJA Methanocaldococcus jannaschii 3 0.7291
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7277
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7277
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7276
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7276
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7249
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7249
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7247
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7247
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7247
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7247
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7225
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7225
BMP-2-inducible protein kinase Q9NSY1 BMP2K_HUMAN Homo sapiens 2 0.7215
BMP-2-inducible protein kinase Q9NSY1 BMP2K_HUMAN Homo sapiens 2 0.7215
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7200
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7200
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7109
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7109
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7108
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7108
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7106
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7106
Aspartate aminotransferase, mitochondrial P00508 AATM_CHICK Gallus gallus 3 0.7089
Aspartate aminotransferase, mitochondrial P00508 AATM_CHICK Gallus gallus 3 0.7089
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7080
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7080
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7057
Ribonuclease TTHA0252 Q5SLP1 RNSE_THET8 Thermus thermophilus 3 0.7057
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7047
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7047
Tryptophan--tRNA ligase Q9PIB4 SYW_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 4 0.7046
Tryptophan--tRNA ligase Q9PIB4 SYW_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 4 0.7046
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7045
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7045
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7045
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7045
Serine/threonine-protein kinase RIO1 Q9BRS2 RIOK1_HUMAN Homo sapiens 3 0.7026
Serine/threonine-protein kinase RIO1 Q9BRS2 RIOK1_HUMAN Homo sapiens 3 0.7026
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7017
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7017

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