Caffeic acid phenolic ester - Compound Card

Caffeic acid phenolic ester

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Caffeic acid phenolic ester

Structure
Zoomed Structure
  • Family: Plantae - Tamaricaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles O=C(Oc1ccc(cc1)O)/C=C/c1ccc(c(c1)O)O
InChI InChI=1S/C15H12O5/c16-11-3-5-12(6-4-11)20-15(19)8-2-10-1-7-13(17)14(18)9-10/h1-9,16-18H/b8-2+
InChIKey FQVRDZTXNYRMFP-KRXBUXKQSA-N
Formula C15H12O5
HBA 5
HBD 3
MW 272.26
Rotatable Bonds 3
TPSA 86.99
LogP 2.42
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.0
Exact Mass 272.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tamarix africana Tamaricaceae Plantae 189784

Showing of synonyms

  • Chekroun-Bechlaghem N, Belyagoubi-Benhammou N, et al. (2021). Antimicrobial and anti-inflammatory activities of three halophyte plants from Algeria and detection of som biomolecules by HPLC-DAD. Natural product research, 2021, 35(12), 2107-2111. [View] [PubMed]
Pubchem: 141395238

No compound-protein relationship available.

Structure

SMILES: c1ccccc1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 272.26 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 272.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.63
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.93
Plasma Protein Binding
48.13
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
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.24
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.6
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.29
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.33
Micronucleos
Toxic
NR-AhR
Toxic
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Toxic
NR-ER-LBD
Toxic
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
5.37
Rat (Acute)
2.13
Rat (Chronic Oral)
2.7
Fathead Minnow
4.48
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
424.16
Hydration Free Energy
-10.93
Log(D) at pH=7.4
2.22
Log(P)
2.33
Log S
-2.79
Log(Vapor Pressure)
-7.89
Melting Point
207.84
pKa Acid
8.23
pKa Basic
6.0
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.9601
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9471
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9360
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 4 0.9205
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.9160
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9132
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9121
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9116
Carnitine O-palmitoyltransferase 2, mitochondrial P18886 CPT2_RAT Rattus norvegicus 3 0.9107
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8973
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.8819
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8772
S-norcoclaurine synthase Q67A25 NCS_THLFG Thalictrum flavum subsp. glaucum 3 0.8718
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8713
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8709
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8684
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 4 0.8611
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8532
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8418
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8366
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8358
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8314
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8277
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.8272
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.8177
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8175
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8166
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8165
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8161
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8082
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8032
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8026
NADPH-dependent 7-cyano-7-deazaguanine reductase Q9KTK0 QUEF_VIBCH Vibrio cholerae serotype O1 3 0.7905
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 3 0.7876
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7843
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7842
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7836
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7808
Beta-lactamase Q79MP6 Q79MP6_PSEAI Pseudomonas aeruginosa 2 0.7799
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7784
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7779
Thymidylate kinase Q8I4S1 Q8I4S1_PLAF7 Plasmodium falciparum 4 0.7773
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7741
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7697
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7691
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7687
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7682
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7679
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7672
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7660
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7652
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7586
ALK tyrosine kinase receptor Q9UM73 ALK_HUMAN Homo sapiens 3 0.7554
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 4 0.7522
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7520
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7511
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7507
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7501
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 3 0.7490
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 3 0.7457
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7451
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7416
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7415
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7415
Aminopeptidase N P04825 AMPN_ECOLI Escherichia coli 3 0.7407
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7407
Putative FAD-dependent oxygenase EncM Q9KHK2 Q9KHK2_9ACTN Streptomyces maritimus 3 0.7406
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7405
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7384
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7383
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7376
Glycogen phosphorylase, liver form P06737 PYGL_HUMAN Homo sapiens 3 0.7363
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7361
Cytochrome P450 3A4 P08684 CP3A4_HUMAN Homo sapiens 4 0.7335
Pol polyprotein Q90K99 Q90K99_9HIV1 Human immunodeficiency virus 1 3 0.7314
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7314
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7308
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7304
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7297
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7288
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7286
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7284
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7281
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 2 0.7279
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7277
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7248
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7243
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.7240
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7237
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 2 0.7231
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7222
Cell division protein FtsZ P0A029 FTSZ_STAAM Staphylococcus aureus 3 0.7220
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7207
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7203
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7186
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7178
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7178
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7177
clade A/E 93TH057 HIV-1 gp120 core A0A0M3KKW9 A0A0M3KKW9_9HIV1 Human immunodeficiency virus 1 2 0.7174
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7167
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7159
Matrilysin P09237 MMP7_HUMAN Homo sapiens 3 0.7155
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7153
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7153
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7148
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7135
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7134
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7118
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7113
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7103
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7100
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7097
Protein-tyrosine kinase 2-beta Q14289 FAK2_HUMAN Homo sapiens 3 0.7096
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 2 0.7088
TamL D3Y1I2 D3Y1I2_9ACTN Streptomyces sp. 307-9 3 0.7085
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7078
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7077
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7075
Unconventional myosin-Va Q02440 MYO5A_CHICK Gallus gallus 2 0.7070
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7069
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 3 0.7052
Glycine N-methyltransferase P13255 GNMT_RAT Rattus norvegicus 4 0.7050
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 5 0.7044
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7042
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7041
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7040
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7039
Cell division protein FtsZ P0A031 FTSZ_STAAU Staphylococcus aureus 3 0.7037
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 2 0.7036
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7027
Formate--tetrahydrofolate ligase Q2RM91 FTHS_MOOTA Moorella thermoacetica 2 0.7017
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 2 0.7016
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7013
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7010
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7007

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