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Chlorogenic acid methyl ester
- Family: Plantae - Asteraceae
- Kingdom: Plantae
- Class: Phenolic
| Canonical Smiles | COC(=O)[C@]1(O)C[C@@H](O)[C@H]([C@@H](C1)OC(=O)/C=C/c1ccc(c(c1)O)O)O |
|---|---|
| InChI | InChI=1S/C17H20O9/c1-25-16(23)17(24)7-12(20)15(22)13(8-17)26-14(21)5-3-9-2-4-10(18)11(19)6-9/h2-6,12-13,15,18-20,22,24H,7-8H2,1H3/b5-3+/t12-,13-,15-,17+/m1/s1 |
| InChIKey | MZNIJRAPCCELQX-AWOKGZDASA-N |
| Formula | C17H20O9 |
| HBA | 9 |
| HBD | 5 |
| MW | 368.34 |
| Rotatable Bonds | 4 |
| TPSA | 153.75 |
| LogP | -0.56 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.41 |
| Exact Mass | 368.11 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Atractylis cancellata | Asteraceae | Plantae | 143173 |
Showing of synonyms
Chlorogenic acid methyl ester
Methyl chlorogenate
Methyl 5-o-caffeoylquinate
Chlorogenic acid, methyl ester
UNII-E6GC3KV7JK
E6GC3KV7JK
Chlorogenic methyl ester
Cyclohexanecarboxylic acid, 3-(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,4,5-trihydroxy-, methyl ester, (1S,3R,4R,5R)-
Cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,4,5-trihydroxy-, methyl ester, (1S,3R,4R,5R)-
Cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, methyl ester, (1S-(1alpha,3beta,4alpha,5alpha))-
3-O-Caffeoylquinic acid methyl ester
123483-19-2
29708-87-0
CHEMBL416955
Methyl (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylate
Methyl (1S,3R,4R,5R)-3-(((E)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylate
Methyl (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxy-cyclohexanecarboxylate
Methyl Chlorogenic Acid
HY-N4168B
MZNIJRAPCCELQX-AWOKGZDASA-
CHEBI:145094
DTXSID501289036
HY-N4168
BDBM50343049
NSC741645
AKOS037514511
AKOS040763658
FS-7815
NSC-741645
DA-49620
DA-55393
FC177959
CS-0032297
CS-0618388
E80658
G14242
Q27276938
(1S,3R,4R,5R)-3-[(E)-3-(3,4-Dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic acid methyl ester
CYCLOHEXANECARBOXYLIC ACID, 3-((3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-1,4,5-TRIHYDROXY-, METHYL ESTER, (1S-(1.ALPHA.,3.BETA.,4.ALPHA.,5.ALPHA.))-
Cyclohexanecarboxylic acid, 3-(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl-Oxy-1,4,5-trihydroxy-, methyl ester, (1S,3R,4R,5R)-
InChI=1/C17H20O9/c1-25-16(23)17(24)7-12(20)15(22)13(8-17)26-14(21)5-3-9-2-4-10(18)11(19)6-9/h2-6,12-13,15,18-20,22,24H,7-8H2,1H3/b5-3+/t12-,13-,15-,17+/m1/s1
Methyl (1S,3R,4R,5R)-3-((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylate
Pubchem:
6476139
Cas:
123483-19-2
Gnps:
CCMSLIB00006516309
Zinc:
ZINC000006482465
Chebi:
145094
Nmrshiftdb2:
20172585
Chembl:
CHEMBL416955
Bindingdb:
50343049
CPRiL:
352239
SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 368.34 g/mol
SMILES: C1CCCCC1
Level: 0
Mol. Weight: 368.34 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 368.34 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.89
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.900
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.05
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.540
- Plasma Protein Binding
- 56.9
- 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
- Non-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
- 11.190
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -1.580
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.630
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.540
- 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
- -2.770
- Rat (Acute)
- 2.010
- Rat (Chronic Oral)
- 3.330
- Fathead Minnow
- 4.120
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 454.100
- Hydration Free Energy
- -13.570
- Log(D) at pH=7.4
- 0.560
- Log(P)
- 0.23
- Log S
- -2.49
- Log(Vapor Pressure)
- -8.74
- Melting Point
- 167.48
- pKa Acid
- 6.0
- pKa Basic
- 4.2
| 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 | 0.9273 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.9206 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9164 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9115 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8770 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8706 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8699 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 4 | 0.8651 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 3 | 0.8445 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8399 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8361 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.8276 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8209 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 3 | 0.8185 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8184 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8056 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8036 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7925 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7899 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7889 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7883 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.7799 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7787 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7787 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7779 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7712 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 2 | 0.7700 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7698 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7675 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7620 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7605 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 3 | 0.7448 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7430 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7399 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7397 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7366 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7317 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7289 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7260 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7259 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7246 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7224 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7221 |
| histidine kinase | O32393 | O32393_ARTPT | Arthrospira platensis | 3 | 0.7209 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7199 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7196 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7165 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7149 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7143 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7138 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.7138 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7130 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7117 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7111 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7105 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7094 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7090 |
| Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 | Q8GZB6 | SUVH4_ARATH | Arabidopsis thaliana | 3 | 0.7084 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7060 |
| DNA ligase | P43813 | DNLJ_HAEIN | Haemophilus influenzae | 3 | 0.7051 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7045 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7041 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 2 | 0.7033 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7011 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7007 |