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6-O-caffeoyl-D-glucopyranoside
- Family: Plantae - Rosaceae
- Kingdom: Plantae
-
Class: Phenylpropanoid
- Subclass: Phenylpropanoid Glucoside
| Canonical Smiles | O=C(/C=C/c1ccc(c(c1)O)O)OC[C@H]1OC(O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C15H18O9/c16-8-3-1-7(5-9(8)17)2-4-11(18)23-6-10-12(19)13(20)14(21)15(22)24-10/h1-5,10,12-17,19-22H,6H2/b4-2+/t10-,12-,13+,14-,15?/m1/s1 |
| InChIKey | JVVFTHAOTNXPOZ-SSLCBRODSA-N |
| Formula | C15H18O9 |
| HBA | 9 |
| HBD | 6 |
| MW | 342.3 |
| Rotatable Bonds | 4 |
| TPSA | 156.91 |
| LogP | -1.55 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.4 |
| Exact Mass | 342.1 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Prunus ssiori | Rosaceae | Plantae | 1926489 |
Showing of synonyms
6-O-caffeoyl-D-glucopyranoside
6-O-(E)-Caffeoylglucopyranose
209797-79-5
6-O-caffeoyl-d-glucopyranose
CHEMBL3590583
C15H18O9
FS-8223
- Abdallah O, Kamel M, et al. (1994). Phenylpropanoid glycosides of Prunus ssiori. Phytochemistry, 1994, 37(6), 1689-1692. [View]
No compound-protein relationship available.
SMILES: O1CCCCC1COC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 342.3 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 342.3 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 342.3 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.64
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.87
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.61
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.62
- Plasma Protein Binding
- 54.01
- 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
- 10.87
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -2.29
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.95
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.65
- 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
- 0.55
- Rat (Acute)
- 1.82
- Rat (Chronic Oral)
- 3.58
- Fathead Minnow
- 4.09
- 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
- 502.08
- Hydration Free Energy
- -18.99
- Log(D) at pH=7.4
- -0.56
- Log(P)
- -1.07
- Log S
- -1.7
- Log(Vapor Pressure)
- -13.67
- Melting Point
- 175.9
- pKa Acid
- 5.57
- pKa Basic
- 6.32
| 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 | 0.9353 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.9153 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9020 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8952 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8854 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8741 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.8707 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8679 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8493 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 3 | 0.8438 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8347 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8313 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8284 |
| Aminoglycoside N(3)-acetyltransferase | A0A3P1UCA6 | Q81P86_BACAN | Bacillus anthracis | 3 | 0.8259 |
| Caffeic acid O-methyltransferase | Q9ZTU2 | Q9ZTU2_LOLPR | Lolium perenne | 4 | 0.8090 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8086 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.8080 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7975 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7937 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7886 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7876 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7815 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7781 |
| Tyrosine-protein kinase JAK1 | P23458 | JAK1_HUMAN | Homo sapiens | 3 | 0.7736 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7683 |
| Tetracycline repressor protein class B from transposon Tn10 | P04483 | TETR2_ECOLX | Escherichia coli | 3 | 0.7682 |
| DNA gyrase subunit A | P0AES5 | GYRA_SHIFL | Shigella flexneri | 3 | 0.7672 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 3 | 0.7661 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7651 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7611 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 4 | 0.7608 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7545 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7543 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7525 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7498 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7494 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7491 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7484 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7466 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7460 |
| Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7424 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7421 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7407 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7404 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7370 |
| Tubulin--tyrosine ligase | F6Z895 | A9ULH4_XENTR | Xenopus tropicalis | 4 | 0.7367 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7333 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7321 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7314 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7284 |
| APH(2'')-Id | O68183 | O68183_ENTCA | Enterococcus casseliflavus | 3 | 0.7282 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7280 |
| Class 10 plant pathogenesis-related protein 2B | Q9LLQ2 | P102B_LUPLU | Lupinus luteus | 2 | 0.7280 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7267 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7257 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7243 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7242 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7239 |
| Threonine--tRNA ligase | P0A8M3 | SYT_ECOLI | Escherichia coli | 3 | 0.7233 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7227 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7224 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.7213 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7198 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7185 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7180 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7163 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7156 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7154 |
| Uncharacterized protein YML079W | Q03629 | YMH9_YEAST | Saccharomyces cerevisiae | 2 | 0.7150 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7144 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7129 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7126 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7125 |
| Tryptophan--tRNA ligase | Q9PIB4 | SYW_CAMJE | Campylobacter jejuni subsp. jejuni serotype O:2 | 4 | 0.7121 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 2 | 0.7118 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7117 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7110 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 3 | 0.7109 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7100 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7098 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7091 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 5 | 0.7089 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7087 |
| Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 | Q8GZB6 | SUVH4_ARATH | Arabidopsis thaliana | 3 | 0.7083 |
| Histone-lysine N-methyltransferase EHMT2 | Q96KQ7 | EHMT2_HUMAN | Homo sapiens | 3 | 0.7071 |
| Anthranilate phosphoribosyltransferase | P00500 | TRPD_ACIAD | Acinetobacter baylyi | 2 | 0.7069 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7062 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7050 |
| Gentisate 1,2-dioxygenase | Q67FT0 | Q67FT0_PSESE | Pseudaminobacter salicylatoxidans | 2 | 0.7047 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 2 | 0.7041 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7041 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7025 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 2 | 0.7021 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7016 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 4 | 0.7002 |