(Z)-4-coumaric acid 4-O-beta-D-apiofuranosyl-(1’’→2’)-O-beta-D-glucopyranoside - Compound Card

(Z)-4-coumaric acid 4-O-beta-D-apiofuranosyl-(1’’→2’)-O-beta-D-glucopyranoside

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(Z)-4-coumaric acid 4-O-beta-D-apiofuranosyl-(1’’→2’)-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Acanthaceae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles OCC1C[C@@H](Oc2ccc(cc2)/C=C\C(=O)O)C(C(C1O)O)OC1OCC(C1O)(O)CO
InChI InChI=1S/C21H28O11/c22-8-12-7-14(31-13-4-1-11(2-5-13)3-6-15(24)25)18(17(27)16(12)26)32-20-19(28)21(29,9-23)10-30-20/h1-6,12,14,16-20,22-23,26-29H,7-10H2,(H,24,25)/b6-3-/t12?,14-,16?,17?,18?,19?,20?,21?/m1/s1
InChIKey MJWNVXWRNYLZIG-GDXCHRBKSA-N
Formula C21H28O11
HBA 10
HBD 7
MW 456.44
Rotatable Bonds 8
TPSA 186.37
LogP -1.91
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.57
Exact Mass 456.16
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Eremomastax speciosa Acanthaceae Plantae 37794

Showing of synonyms

  • Eve MO, Alfred TN, et al. (2020). Chemical constituents of Erememostax speciosa (HOCHST.) cufod leaves and its cytotoxic potential on NIH-3T3 cells. Bulletin of the Chemical Society of Ethiopia,2020,34(3),634-640. [View]

No compound-protein relationship available.

Structure

SMILES: O1CCCC1OC2C(CCCC2)Oc3ccccc3

Level: 2

Mol. Weight: 456.44 g/mol

Structure

SMILES: c1ccccc1OC2CCCCC2

Level: 1

Mol. Weight: 456.44 g/mol

Structure

SMILES: O1CCCC1OC2CCCCC2

Level: 1

Mol. Weight: 456.44 g/mol

Structure

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 456.44 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 456.44 g/mol

Structure

SMILES: C1CCOC1

Level: 0

Mol. Weight: 456.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.45
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.46
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-1.35

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.74
Plasma Protein Binding
17.52
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
3.6
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-3.09
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.6
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.24
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
-67.54
Rat (Acute)
2.21
Rat (Chronic Oral)
3.76
Fathead Minnow
3.97
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
541.44
Hydration Free Energy
-3.98
Log(D) at pH=7.4
-2.43
Log(P)
-0.7
Log S
-1.72
Log(Vapor Pressure)
-13.22
Melting Point
167.52
pKa Acid
2.57
pKa Basic
5.81
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8741
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8680
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8472
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8453
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 3 0.8401
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8219
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8172
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8106
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 3 0.8027
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8010
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7994
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7749
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7675
Deacetoxycephalosporin C synthase P18548 CEFE_STRCL Streptomyces clavuligerus 3 0.7645
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7635
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7519
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 3 0.7401
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.7378
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7291
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7261
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7256
Large structural protein Q91L20 Q91L20_9MONO Human metapneumovirus 3 0.7214
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7202
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7170
Egl nine homolog 1 Q9GZT9 EGLN1_HUMAN Homo sapiens 2 0.7131
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7107
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7091
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7089
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7080
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7057
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7039
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7017

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