Caffeoyl-hydrocitric acid - Compound Card

Caffeoyl-hydrocitric acid

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Caffeoyl-hydrocitric acid

Structure
Zoomed Structure
  • Family: Plantae - Malvaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles OC(=O)CC(C(C(=O)O)OC(=O)/C=C/c1ccc(c(c1)O)O)(C(=O)O)O
InChI InChI=1S/C15H14O11/c16-8-3-1-7(5-9(8)17)2-4-11(20)26-12(13(21)22)15(25,14(23)24)6-10(18)19/h1-5,12,16-17,25H,6H2,(H,18,19)(H,21,22)(H,23,24)/b4-2+
InChIKey OUWOVSUGDPWIBY-DUXPYHPUSA-N
Formula C15H14O11
HBA 8
HBD 6
MW 370.27
Rotatable Bonds 8
TPSA 198.89
LogP -0.6
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.2
Exact Mass 370.05
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Hibiscus noldeae Malvaceae Plantae 47605

Showing of synonyms

  • Tomani JCD, Kagisha V, et al. (2020). The Inhibition of NLRP3 Inflammasome and IL-6 Production by Hibiscus noldeae Baker f. Derived Constituents Provides a Link to Its Anti-Inflammatory Therapeutic Potentials. Molecules. 2020, 25(20), 4693. [View] [PubMed]
Pubchem: 24797519
Chebi: 169788

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 370.27 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.24
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.77
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-5.2

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
-0.05
Plasma Protein Binding
5.34
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
1.27
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.27
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.04
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.54
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
10.87
Rat (Acute)
1.84
Rat (Chronic Oral)
4.06
Fathead Minnow
3.71
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
418.94
Hydration Free Energy
-7.7
Log(D) at pH=7.4
-5.87
Log(P)
-0.07
Log S
-1.08
Log(Vapor Pressure)
-13.49
Melting Point
186.6
pKa Acid
2.54
pKa Basic
7.03
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 0.9264
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9156
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9121
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9040
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 3 0.9032
Avidin P02701 AVID_CHICK Gallus gallus 3 0.9015
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8934
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.8931
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8668
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8620
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8598
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8590
MutT/nudix family protein Q5SJY9 Q5SJY9_THET8 Thermus thermophilus 3 0.8526
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 3 0.8485
Geranyl diphosphate synthase large subunit Q9SBR3 Q9SBR3_MENPI Mentha piperita 3 0.8472
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8462
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8364
Eukaryotic translation initiation factor 4E type 2 O60573 IF4E2_HUMAN Homo sapiens 5 0.8236
Uncharacterized protein Q8DY32 Q8DY32_STRA5 Streptococcus agalactiae serotype V 5 0.8234
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 3 0.8231
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8209
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 3 0.8152
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8141
Malate dehydrogenase P10584 MDH_THETH Thermus thermophilus 4 0.8099
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 3 0.8098
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8093
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8087
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8066
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7927
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7923
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7912
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 3 0.7887
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7883
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7879
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 4 0.7868
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7777
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7739
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase B1MKD5 B1MKD5_MYCA9 Mycobacteroides abscessus 3 0.7715
Caffeic acid 3-O-methyltransferase P28002 COMT1_MEDSA Medicago sativa 3 0.7708
non-specific serine/threonine protein kinase Q6FS46 Q6FS46_CANGA Candida glabrata 4 0.7698
RNA-directed RNA polymerase P11124 RDRP_BPPH6 Pseudomonas phage phi6 3 0.7684
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7676
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 4 0.7649
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7621
Chemotaxis protein CheA Q56310 CHEA_THEMA Thermotoga maritima 3 0.7606
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7529
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7522
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7517
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7517
Riboflavin biosynthesis protein Q9WZW1 Q9WZW1_THEMA Thermotoga maritima 4 0.7490
5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase Q8U0R7 PURP_PYRFU Pyrococcus furiosus 3 0.7465
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7465
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7438
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7425
Farnesyl pyrophosphate synthase P14324 FPPS_HUMAN Homo sapiens 3 0.7412
Probable enoyl-CoA hydratase EchA8 P9WNN9 ECHA8_MYCTU Mycobacterium tuberculosis 4 0.7402
Integrin alpha-5 P08648 ITA5_HUMAN Homo sapiens 3 0.7374
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7371
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7366
Interleukin enhancer-binding factor 2 Q9CXY6 ILF2_MOUSE Mus musculus 3 0.7348
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7346
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7334
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7299
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7271
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 5 0.7264
SRSF protein kinase 1 Q96SB4 SRPK1_HUMAN Homo sapiens 4 0.7250
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7248
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7225
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7219
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7217
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7205
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7199
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7194
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 4 0.7189
Geranylgeranyl pyrophosphate synthase BTS1 Q12051 GGPPS_YEAST Saccharomyces cerevisiae 3 0.7188
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7182
3-hydroxy-3-methylglutaryl-coenzyme A reductase P04035 HMDH_HUMAN Homo sapiens 3 0.7181
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7176
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7175
Amino acid ABC transporter D0VWX4 D0VWX4_GEOSE Geobacillus stearothermophilus 3 0.7163
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7159
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7158
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7143
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7138
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7129
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7125
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7125
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7122
Ectonucleoside triphosphate diphosphohydrolase I Q5ZUA2 Q5ZUA2_LEGPH Legionella pneumophila subsp. pneumophila 3 0.7113
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7099
Mexicain P84346 MEX1_JACME Jacaratia mexicana 3 0.7094
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7071
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7071
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7063
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7059
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 3 0.7055
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7047
Phosphoribosylformylglycinamidine synthase subunit PurL Q9X0X3 PURL_THEMA Thermotoga maritima 3 0.7046
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7043
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7041
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7031
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7028
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7023
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7010
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7009
Glucose-1-phosphate thymidylyltransferase Q9AGY4 Q9AGY4_ANETH Aneurinibacillus thermoaerophilus 4 0.7000

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