6-O-apio-beta-furanosyl-[5-O-(trans-dimethoxycinnamic acid)]-alpha/beta-glucopyranoside - Compound Card

6-O-apio-beta-furanosyl-[5-O-(trans-dimethoxycinnamic acid)]-alpha/beta-glucopyranoside

Select a section from the left sidebar

6-O-apio-beta-furanosyl-[5-O-(trans-dimethoxycinnamic acid)]-alpha/beta-glucopyranoside

Structure
Zoomed Structure
  • Family: Ebenaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles COc1ccc(cc1OC)/C=C/C(=O)OCC1(O)CO[C@@H]([C@H]1O)OC[C@@H]1OC(O)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C22H30O13/c1-30-12-5-3-11(7-13(12)31-2)4-6-15(23)33-9-22(29)10-34-21(19(22)27)32-8-14-16(24)17(25)18(26)20(28)35-14/h3-7,14,16-21,24-29H,8-10H2,1-2H3/b6-4+/t14-,16-,17+,18-,19+,20?,21-,22?/m0/s1
InChIKey HBYHINMQDZPYMK-ZFFAPNLTSA-N
Formula C22H30O13
HBA 13
HBD 6
MW 502.47
Rotatable Bonds 9
TPSA 193.83
LogP -2.47
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 502.17
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Diospyros bipindensis Ebenaceae Plantae 413723

Showing of synonyms

  • Cesari I, Queiroz EF, et al. (2013). Extensive phytochemical investigation of the polar constituents of Diospyros bipindensis Gürke traditionally used by Baka pygmies.. Phytochemistry,2013, 96, 279-287. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)OCC2CC(OC2)OCC3CCCCO3

Level: 2

Mol. Weight: 346.42 g/mol

Structure

SMILES: C1OCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 232.28 g/mol

Structure

SMILES: O1CCCCC1COC2CCCO2

Level: 1

Mol. Weight: 186.25 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 86.13 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 72.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.04
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.070
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.810
Plasma Protein Binding
59.17
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
5.530
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.740
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.040
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.710
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
-267.820
Rat (Acute)
2.250
Rat (Chronic Oral)
3.830
Fathead Minnow
4.120
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
543.920
Hydration Free Energy
-3.430
Log(D) at pH=7.4
0.120
Log(P)
-1.41
Log S
-2.22
Log(Vapor Pressure)
-14.35
Melting Point
158.92
pKa Acid
4.45
pKa Basic
3.2
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.9350
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9227
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8817
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8799
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8747
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8647
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8563
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8288
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8213
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8160
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7805
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7673
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7582
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7579
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7567
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7554
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7528
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7520
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7478
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7469
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7449
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7419
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7371
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7366
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7357
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7345
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7334
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7320
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7315
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7308
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7303
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7298
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7294
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7292
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7289
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7245
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7240
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7238
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7237
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7201
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7200
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 2 0.7199
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7199
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7196
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7189
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7182
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7177
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7177
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7176
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7170
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7160
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7158
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7158
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7156
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7153
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7150
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7139
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7123
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7110
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7108
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7103
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7098
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7094
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 2 0.7092
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7090
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7075
Pantothenate synthetase P9WIL4 PANC_MYCTO Mycobacterium tuberculosis 2 0.7069
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7067
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 2 0.7062
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7062
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7062
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7055
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7048
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7039
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7031
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7022
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7021
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7018
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7016
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 2 0.7015
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7013
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7004

Download SDF