Coumaroyl galloyl-glucopyranoside - Compound Card

Coumaroyl galloyl-glucopyranoside

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Coumaroyl galloyl-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Tamaricaceae
  • Kingdom: Plantae
  • Class: Tannin
Canonical Smiles OC[C@H]1OC(OC(=O)c2cc(O)c(c(c2)O)O)(C(=O)/C=C/c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C22H22O12/c23-9-15-18(29)19(30)20(31)22(33-15,16(27)6-3-10-1-4-12(24)5-2-10)34-21(32)11-7-13(25)17(28)14(26)8-11/h1-8,15,18-20,23-26,28-31H,9H2/b6-3+/t15-,18-,19+,20-,22?/m1/s1
InChIKey NKTYURIEXDRZNY-PMWQZIJWSA-N
Formula C22H22O12
HBA 12
HBD 8
MW 478.41
Rotatable Bonds 6
TPSA 214.44
LogP -0.88
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.27
Exact Mass 478.11
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Tamarix articulata Tamaricaceae Plantae 189786

Showing of synonyms

  • Shaalan Y.M, Handoussa H, et al. (2018). Destabilizing the interplay between miR-1275 and IGF2BPs by Tamarix articulata and quercetin in hepatocellular carcinoma. Nat Prod Res,2018,32(18),2217-2220. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C=CC(=O)C2(CCCCO2)OC(=O)c3ccccc3

Level: 2

Mol. Weight: 478.41 g/mol

Structure

SMILES: O1CCCCC1C(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 478.41 g/mol

Structure

SMILES: c1ccccc1C(=O)OC2CCCCO2

Level: 1

Mol. Weight: 478.41 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 478.41 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 478.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.87
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.68
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-0.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.67
Plasma Protein Binding
62.61
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
11.3
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.84
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.87
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.92
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
-126.81
Rat (Acute)
2.25
Rat (Chronic Oral)
3.96
Fathead Minnow
4.13
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
640.92
Hydration Free Energy
-3.95
Log(D) at pH=7.4
-0.72
Log(P)
-0.52
Log S
-3.49
Log(Vapor Pressure)
-12.45
Melting Point
180.52
pKa Acid
4.41
pKa Basic
7.98
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 0.9224
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8515
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8498
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8406
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.8266
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8236
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8226
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8163
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8061
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8056
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8055
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7995
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7942
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7853
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7709
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.7696
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7682
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7655
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7644
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7628
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7526
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 3 0.7519
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7470
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7464
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7370
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7349
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 4 0.7302
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7282
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7264
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7260
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7217
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7216
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7187
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7181
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7170
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7167
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7159
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7153
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7150
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7122
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7115
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7106
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7087
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7073
Tryptase alpha/beta-1 Q15661 TRYB1_HUMAN Homo sapiens 3 0.7066
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7049
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7024
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7019
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7008

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