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

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

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6-O-apio-beta-furanosyl-[5-O-(cis-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-FSJKCEPESA-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
59.33
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
5.520
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.800
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
5.700
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
-269.700
Rat (Acute)
2.250
Rat (Chronic Oral)
3.820
Fathead Minnow
3.970
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
543.440
Hydration Free Energy
-3.430
Log(D) at pH=7.4
0.110
Log(P)
-1.37
Log S
-2.2
Log(Vapor Pressure)
-14.38
Melting Point
152.97
pKa Acid
4.44
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 0.9385
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9319
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8916
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8909
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8876
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8738
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8561
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8410
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8288
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7963
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7936
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7858
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7795
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7728
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7711
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7708
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7677
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7624
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7540
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7512
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7484
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7452
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7440
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7436
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7432
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7368
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7362
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7340
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7322
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7321
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7320
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7318
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7295
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7289
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7265
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7251
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.7242
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7241
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7237
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7231
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 2 0.7227
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase P0AF12 MTNN_ECOLI Escherichia coli 2 0.7208
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 2 0.7195
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 2 0.7195
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7187
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 2 0.7165
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7150
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 2 0.7145
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7136
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7135
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7129
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7101
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7096
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7091
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 2 0.7083
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7081
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7078
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7078
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7074
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7073
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7072
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7070
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7068
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7066
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7065
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7051
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7050
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7047
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase P47229 BPHD_PARXL Paraburkholderia xenovorans 2 0.7039
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7034
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7033
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7029
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7023
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7021
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7018
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7016
Putative FAD-dependent oxygenase EncM Q9KHK2 Q9KHK2_9ACTN Streptomyces maritimus 2 0.7016
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7002
Aspartate aminotransferase, mitochondrial P00508 AATM_CHICK Gallus gallus 2 0.7002

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