2-propenoic acid, 3-(4-(acetyloxy)-3-methoxypheny)-3-(4-acetyloxy)-3-methoxyphenyl)-2-propenyl ester - Compound Card

2-propenoic acid, 3-(4-(acetyloxy)-3-methoxypheny)-3-(4-acetyloxy)-3-methoxyphenyl)-2-propenyl ester

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2-propenoic acid, 3-(4-(acetyloxy)-3-methoxypheny)-3-(4-acetyloxy)-3-methoxyphenyl)-2-propenyl ester

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Ester
    • Subclass: Diester Of Caffeic Acid Derivative
Canonical Smiles C(=O)(C=C(c1ccc(c(c1)OC)OC(=O)C)c1ccc(c(c1)OC)OC(=O)C)OCC=C
InChI InChI=1S/C24H24O8/c1-6-11-30-24(27)14-19(17-7-9-20(31-15(2)25)22(12-17)28-4)18-8-10-21(32-16(3)26)23(13-18)29-5/h6-10,12-14H,1,11H2,2-5H3
InChIKey BVJVPVQAZMEADU-UHFFFAOYSA-N
Formula C24H24O8
HBA 8
HBD 0
MW 440.45
Rotatable Bonds 9
TPSA 97.36
LogP 3.72
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 32
Formal Charge 0
Fraction CSP3 0.21
Exact Mass 440.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tephrosia apollinea Leguminosae/Fabaceae Plantae 1390541
2 Tephrosia purpurea Leguminosae/Fabaceae Plantae 228354

Showing of synonyms

  • Khalafalah A.K, Yousef A.H, et al. (2010). Chemical constituents of Tephrosia purpurea. Pharmacognosy research, 2010, 2(2), 72-5. [View] [PubMed]
  • Khalafallah A, Suleiman S, et al. (2009). Prenylated flavonoids from Tephrosia apollinea. Chinese Chemical Letters, 2009, 20(12), 1465-1468. [View]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=C)c2ccccc2

Level: 1

Mol. Weight: 440.45 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 440.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.26
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.640
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.83

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.930
Plasma Protein Binding
27.4
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.770
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.220
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.200
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.060
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-43.100
Rat (Acute)
2.490
Rat (Chronic Oral)
2.490
Fathead Minnow
5.580
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
458.220
Hydration Free Energy
-3.610
Log(D) at pH=7.4
3.980
Log(P)
3.46
Log S
-5.56
Log(Vapor Pressure)
-7.52
Melting Point
93.82
pKa Acid
10.09
pKa Basic
1.89
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9137
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8949
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8730
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8677
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8677
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8627
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8598
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8478
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.8476
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8468
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8431
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8398
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8374
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8374
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8308
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8173
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.7985
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7954
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7948
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7931
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7913
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7896
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7878
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7876
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7857
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7850
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7795
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7759
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7716
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7696
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.7692
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7692
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7643
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7583
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7573
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7558
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7546
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7534
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7528
High affinity nerve growth factor receptor P04629 NTRK1_HUMAN Homo sapiens 3 0.7526
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7526
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7526
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7512
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 2 0.7500
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7497
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7497
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7495
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7478
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7467
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7449
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7442
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7436
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7434
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7417
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7408
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7407
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7404
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7400
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7390
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7387
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7379
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 2 0.7372
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7358
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7357
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7349
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7342
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7342
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7335
Mineralocorticoid receptor P08235 MCR_HUMAN Homo sapiens 3 0.7331
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7286
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7275
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7264
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7261
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7257
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7252
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7243
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7233
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7221
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7219
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7212
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7209
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7201
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7191
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7186
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7182
Dihydropteroate synthase Q81VW8 Q81VW8_BACAN Bacillus anthracis 3 0.7156
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7154
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7143
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7136
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7132
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7124
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7116
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7115
Glycerol kinase P0A6F3 GLPK_ECOLI Escherichia coli 4 0.7114
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 4 0.7103
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7101
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7100
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7096
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7096
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7091
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7084
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7080
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7076
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7070
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7069
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7057
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7050
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7043
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7038
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7034
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7031
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7025
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7025
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7022
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7018
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7008
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7006
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7003
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7000

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