6-O-[5-O-(trans-ferulic acid)-beta-apiofuranosyl]-alpha/beta-glucopyranoside - Compound Card

6-O-[5-O-(trans-ferulic acid)-beta-apiofuranosyl]-alpha/beta-glucopyranoside

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6-O-[5-O-(trans-ferulic acid)-beta-apiofuranosyl]-alpha/beta-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Ebenaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles COc1cc(/C=C/C(=O)OCC2(O)CO[C@@H]([C@H]2O)OC[C@@H]2OC(O)[C@H]([C@@H]([C@H]2O)O)O)ccc1O
InChI InChI=1S/C21H28O13/c1-30-12-6-10(2-4-11(12)22)3-5-14(23)32-8-21(29)9-33-20(18(21)27)31-7-13-15(24)16(25)17(26)19(28)34-13/h2-6,13,15-20,22,24-29H,7-9H2,1H3/b5-3+/t13-,15-,16+,17-,18+,19?,20-,21?/m0/s1
InChIKey HORSEUYDTNGPHR-LVYVGWOASA-N
Formula C21H28O13
HBA 13
HBD 7
MW 488.44
Rotatable Bonds 8
TPSA 204.83
LogP -2.78
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 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: 488.44 g/mol

Structure

SMILES: C1OCCC1COC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 488.44 g/mol

Structure

SMILES: O1CCCCC1COC2CCCO2

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

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 488.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.25
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.180
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.17

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.760
Plasma Protein Binding
57.22
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
7.480
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.870
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.910
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.880
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
-155.880
Rat (Acute)
2.020
Rat (Chronic Oral)
3.860
Fathead Minnow
4.130
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
559.940
Hydration Free Energy
-3.460
Log(D) at pH=7.4
-0.240
Log(P)
-1.61
Log S
-2.37
Log(Vapor Pressure)
-14.93
Melting Point
174.81
pKa Acid
3.93
pKa Basic
4.58
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 0.9529
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9475
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9315
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.9246
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9029
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9008
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8952
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8903
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8896
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8828
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8817
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8795
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8755
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8740
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8724
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8696
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8482
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8422
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8412
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8376
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8339
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8324
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8268
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8185
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8184
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8112
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8109
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8048
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8038
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7926
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7894
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7879
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7854
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7813
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7735
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7698
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7652
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7636
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7618
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7593
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7586
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7572
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7542
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7539
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7527
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7514
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7473
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7467
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7461
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7458
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7458
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7428
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7424
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7407
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7406
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7389
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7371
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7370
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7354
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7353
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7346
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7342
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7340
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7339
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7339
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 2 0.7333
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7323
DNA-(apurinic or apyrimidinic site) lyase Q97FM4 Q97FM4_CLOAB Clostridium acetobutylicum 4 0.7322
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7319
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7317
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7314
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7312
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7311
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7311
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7310
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7305
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7300
Cytochrome b-c1 complex subunit 1, mitochondrial P31800 QCR1_BOVIN Bos taurus 3 0.7295
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7295
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7270
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7264
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7262
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7257
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7253
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7250
Probable bifunctional SAT/APS kinase O67174 SATC_AQUAE Aquifex aeolicus 3 0.7248
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7239
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 2 0.7239
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7212
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7208
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7208
Mitogen-activated protein kinase kinase kinase 7 O43318 M3K7_HUMAN Homo sapiens 3 0.7194
DNA (cytosine-5)-methyltransferase 3A O88508 DNM3A_MOUSE Mus musculus 3 0.7192
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7191
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7179
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7177
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7177
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 4 0.7163
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 2 0.7160
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7160
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7154
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7151
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7151
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7147
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7145
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7144
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7138
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7138
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7137
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7125
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7124
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7123
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7123
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7122
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7101
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7099
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7093
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7092
Transitional endoplasmic reticulum ATPase Q01853 TERA_MOUSE Mus musculus 3 0.7087
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7080
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7076
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7074
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7074
Transitional endoplasmic reticulum ATPase P55072 TERA_HUMAN Homo sapiens 3 0.7067
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7066
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7063
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 3 0.7061
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7060
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7059
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7054
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7046
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7044
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7039
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7033
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 3 0.7032
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7031
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 2 0.7021
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 3 0.7017
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7017
Casein kinase II subunit alpha P15790 CSK21_YEAST Saccharomyces cerevisiae 4 0.7014
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7010
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase P47229 BPHD_PARXL Paraburkholderia xenovorans 2 0.7010
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7009
Neprilysin P08049 NEP_RABIT Oryctolagus cuniculus 4 0.7008
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7008
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7007
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 2 0.7001

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