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5-O-caffeoylshikimic acid
- Family: Plantae - Asteraceae
- Kingdom: Plantae
- Class: Phenolic
| Canonical Smiles | O=C(O[C@@H]1CC(=C[C@H]([C@H]1O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/b4-2+/t12-,13-,15-/m1/s1 |
| InChIKey | QMPHZIPNNJOWQI-GDDAOPKQSA-N |
| Formula | C16H16O8 |
| HBA | 7 |
| HBD | 5 |
| MW | 336.3 |
| Rotatable Bonds | 4 |
| TPSA | 144.52 |
| LogP | 0.16 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.25 |
| Exact Mass | 336.08 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Atractylis cancellata | Asteraceae | Plantae | 143173 |
Showing of synonyms
5-O-caffeoylshikimic acid
Dactylifric acid
5-caffeoylshikimic acid
5U399BD0RZ
5-CSA
TRANS-5-O-CAFFEOYLSHIKIMIC ACID
1-CYCLOHEXENE-1-CARBOXYLIC ACID, 3-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-4,5-DIHYDROXY-, (3R,4R,5R)-
1-CYCLOHEXENE-1-CARBOXYLIC ACID, 5-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-3,4-DIHYDROXY-, (3R,4R,5R)-
73263-62-4
(3R,4R,5R)-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxycyclohexene-1-carboxylic acid
MEGxp0_000239
ACon1_000160
1-Cyclohexene-1-carboxylic acid, 5-((3-(3,4-dihydroxyphenyl)-1-oxo-2-p ropenyl)oxy)-3,4-dihydroxy-, (3R-(3alpha,4alpha,5beta))-
(3R,4R,5R)-5-(((E)-3-(3,4-Dihydroxyphenyl)acryloyl)oxy)-3,4-dihydroxycyclohex-1-enecarboxylic acid
AC1NQZ12
UNII-5U399BD0RZ
(3R,4R,5R)-5-[[3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-3,4-dihydroxy-1-cyclohexene-1-carboxylic Acid
CHEBI:2106
5-(trans-caffeoyl)shikimic acid
5-[(E)-caffeoyl]shikimic acid
MolPort-001-740-420
DTXSID501312675
HY-N8321
YCA26362
AKOS040760230
NCGC00180823-01
NCGC00180823-02
DA-60469
MS-25090
PD166603
CS-0143081
E80649
Q27105553
(3R,4R,5R)-5-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-3,4-dihydroxy-cyclohexene-1-carboxylic acid
(3R,4R,5R)-5-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid
1-Cyclohexene-1-carboxylic acid, 5-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-3,4-dihydroxy-, (3R-(3alpha,4alpha,5beta))-
CPRiL:
59675
SMILES: C1CC=CCC1OC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 336.3 g/mol
SMILES: C1=CCCCC1
Level: 0
Mol. Weight: 336.3 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 336.3 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.23
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.94
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.35
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.73
- Plasma Protein Binding
- 50.2
- 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
- 10.77
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -1.77
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.31
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.58
- 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
- 0.03
- Rat (Acute)
- 1.75
- Rat (Chronic Oral)
- 3.08
- Fathead Minnow
- 4.05
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 487.38
- Hydration Free Energy
- -14.65
- Log(D) at pH=7.4
- -1.24
- Log(P)
- 0.34
- Log S
- -2.05
- Log(Vapor Pressure)
- -11.39
- Melting Point
- 190.51
- pKa Acid
- 4.7
- pKa Basic
- 5.56
| 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 | 0.9271 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.9182 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9148 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9118 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.9092 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.9043 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.9004 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8766 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8665 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 4 | 0.8610 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.8474 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 3 | 0.8431 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 3 | 0.8402 |
| Branched-chain-amino-acid aminotransferase, mitochondrial | O15382 | BCAT2_HUMAN | Homo sapiens | 3 | 0.8370 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8366 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.8348 |
| Formate--tetrahydrofolate ligase | P21164 | FTHS_MOOTH | Moorella thermoacetica | 3 | 0.8266 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.8257 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8223 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8210 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.8189 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.8171 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8139 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8080 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8057 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 2 | 0.8047 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8009 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7993 |
| Steroid 3-ketoacyl-CoA thiolase | I6XHI4 | FADA5_MYCTU | Mycobacterium tuberculosis | 3 | 0.7985 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7956 |
| Ectonucleoside triphosphate diphosphohydrolase I | Q5ZUA2 | Q5ZUA2_LEGPH | Legionella pneumophila subsp. pneumophila | 3 | 0.7920 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7915 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7884 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7854 |
| 3-dehydroquinate dehydratase | P9WPX7 | AROQ_MYCTU | Mycobacterium tuberculosis | 3 | 0.7843 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7783 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7676 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7672 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7672 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7620 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.7601 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.7518 |
| Hygromycin-B 4-O-kinase | P00557 | KHYB_ECOLX | Escherichia coli | 3 | 0.7512 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7491 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.7489 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7483 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7463 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7405 |
| Activated CDC42 kinase 1 | Q07912 | ACK1_HUMAN | Homo sapiens | 3 | 0.7390 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7390 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7379 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7378 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7367 |
| Probable enoyl-CoA hydratase EchA8 | P9WNN9 | ECHA8_MYCTU | Mycobacterium tuberculosis | 4 | 0.7354 |
| NAD-dependent protein deacetylase sirtuin-3, mitochondrial | Q9NTG7 | SIR3_HUMAN | Homo sapiens | 4 | 0.7346 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7318 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7314 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 3 | 0.7314 |
| 5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase | Q8U0R7 | PURP_PYRFU | Pyrococcus furiosus | 3 | 0.7311 |
| mRNA-capping enzyme subunit alpha | P78587 | MCE1_CANAX | Candida albicans | 3 | 0.7302 |
| Genome polyprotein | A0EKU1 | A0EKU1_9FLAV | Meaban virus | 3 | 0.7264 |
| Shikimate dehydrogenase (NADP(+)) | P56119 | AROE_HELPY | Helicobacter pylori | 3 | 0.7238 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7234 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7228 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7224 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7222 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7217 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7210 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7209 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7202 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7201 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7171 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7168 |
| Hydroxymethylglutaryl-CoA synthase | Q9FD71 | HMGCS_ENTFL | Enterococcus faecalis | 2 | 0.7155 |
| Flavin-dependent monooxygenase | Q93L51 | TETX_BACT4 | Bacteroides thetaiotaomicron | 2 | 0.7148 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7148 |
| Single-stranded-DNA-specific exonuclease RecJ | D0EM60 | D0EM60_DEIRD | Deinococcus radiodurans | 3 | 0.7142 |
| Thymidylate synthase | P04818 | TYSY_HUMAN | Homo sapiens | 4 | 0.7129 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7124 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7119 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7113 |
| UTP-monosaccharide-1-phosphate uridylyltransferase | D3G6S4 | D3G6S4_LEIMA | Leishmania major | 3 | 0.7090 |
| Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 | Q9Y3Z3 | SAMH1_HUMAN | Homo sapiens | 3 | 0.7083 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7073 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 3 | 0.7066 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7066 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 4 | 0.7062 |
| Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 | Q8GZB6 | SUVH4_ARATH | Arabidopsis thaliana | 3 | 0.7051 |
| 3-hydroxy-3-methylglutaryl-coenzyme A reductase | P04035 | HMDH_HUMAN | Homo sapiens | 3 | 0.7035 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7034 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7023 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7014 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7009 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7006 |
| Elongation factor Tu 1 | P0CE47 | EFTU1_ECOLI | Escherichia coli | 3 | 0.7001 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7000 |