Caffeic acid glucorhamnoside - Compound Card

Caffeic acid glucorhamnoside

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Caffeic acid glucorhamnoside

Structure
Zoomed Structure
  • Family: Plantae - Juncaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Glycoside
Canonical Smiles CC[C@@H]1OC(O[C@H]2[C@H](O)OC([C@@H]([C@@H]2O)O)OC(=O)/C=C/c2ccc(c(c2)O)O)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C21H28O13/c1-2-11-13(25)14(26)16(28)20(31-11)33-18-15(27)17(29)21(34-19(18)30)32-12(24)6-4-8-3-5-9(22)10(23)7-8/h3-7,11,13-23,25-30H,2H2,1H3/b6-4+/t11-,13-,14+,15-,16-,17+,18+,19+,20?,21?/m0/s1
InChIKey UTBKBZAPMAXVDW-XCLYCKQCSA-N
Formula C21H28O13
HBA 13
HBD 8
MW 488.44
Rotatable Bonds 6
TPSA 215.83
LogP -2.35
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 488.15
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Juncus acutus Juncaceae Plantae 308385

Showing of synonyms

  • Awaad AS (2006). Phenolic glycosides of Juncus acutus and its anti-eczematic activity. Chemistry of Natural Compounds,2006,42(2),152-155. [View]
Pubchem: 162817168
Nmrshiftdb2: 70090544

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OC(OC2)CCC2OC3CCCCO3

Level: 2

Mol. Weight: 488.44 g/mol

Structure

SMILES: O1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 488.44 g/mol

Structure

SMILES: C1OCCCC1OC2CCCCO2

Level: 1

Mol. Weight: 488.44 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 488.44 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 488.44 g/mol

Anti-eczematic

Absorption

Caco-2 (logPapp)
-6.49
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.38
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.69
Plasma Protein Binding
55.81
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
8.59
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-3.38
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.72
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.5
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
-131.11
Rat (Acute)
1.98
Rat (Chronic Oral)
4.07
Fathead Minnow
4.07
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
576.77
Hydration Free Energy
-3.55
Log(D) at pH=7.4
-0.21
Log(P)
-0.61
Log S
-2.41
Log(Vapor Pressure)
-15.61
Melting Point
173.91
pKa Acid
3.49
pKa Basic
5.5
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 0.9297
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9297
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9203
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9203
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9117
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9117
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8841
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8841
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8771
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8771
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8760
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8760
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8659
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8659
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8444
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8444
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8434
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8434
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8365
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8365
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8208
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8208
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8150
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8150
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8117
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8117
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8088
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8088
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8020
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8020
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8013
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8013
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7993
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7993
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7942
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7942
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7932
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7932
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7925
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7925
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7921
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7921
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7837
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7837
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7785
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7785
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7782
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7782
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7779
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7779
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7698
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7698
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7646
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7646
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7589
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7589
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7521
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7521
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7492
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7492
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7484
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7484
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7449
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7449
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7387
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7387
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7362
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7362
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7342
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7342
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7341
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7341
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7319
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7319
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7311
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7311
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7304
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7304
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7287
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7287
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7256
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7256
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7249
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7249
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7247
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7247
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7242
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7242
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7212
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7212
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7191
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7191
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7186
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7186
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7167
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7167
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7154
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7154
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7153
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7153
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7147
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7147
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7108
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7108
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7108
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7108
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7099
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7099
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7097
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7097
Guanylate kinase P15454 KGUA_YEAST Saccharomyces cerevisiae 3 0.7091
Guanylate kinase P15454 KGUA_YEAST Saccharomyces cerevisiae 3 0.7091
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7089
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7089
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7064
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7064
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7054
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 3 0.7054
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7051
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7051
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7046
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7046
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7038
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7038
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7028
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7028
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7013
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7013
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7006
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7006

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