4-[1-acetoxy-2-(diacetylamino)ethyl]phenyl acetate - Compound Card

4-[1-acetoxy-2-(diacetylamino)ethyl]phenyl acetate

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4-[1-acetoxy-2-(diacetylamino)ethyl]phenyl acetate

Structure
Zoomed Structure
  • Family: Plantae - Chenopodiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CC(=O)OC(c1ccc(cc1)OC(=O)C)CN(C(=O)C)C(=O)C
InChI InChI=1S/C16H19NO6/c1-10(18)17(11(2)19)9-16(23-13(4)21)14-5-7-15(8-6-14)22-12(3)20/h5-8,16H,9H2,1-4H3
InChIKey WXBPPNDYHGULCD-UHFFFAOYSA-N
Formula C16H19NO6
HBA 6
HBD 0
MW 321.33
Rotatable Bonds 5
TPSA 89.98
LogP 1.61
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 321.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Haloxylon scoparium Chenopodiaceae Plantae 1665493

Showing of synonyms

  • Lachkar N, Lamchouri F, et al. (2021). Chemical composition, phenolic content and antioxidant capacity of Haloxylon scoparium extracts. Evidence-based complementary and alternative medicine : eCAM, 2021, 2021, 9011168. [View] [PubMed]
Pubchem: 91711710

No compound-protein relationship available.

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 321.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.65
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.35
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.19
Plasma Protein Binding
15.89
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
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
6.18
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.06
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.68
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.95
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
1.24
Rat (Acute)
2.06
Rat (Chronic Oral)
1.93
Fathead Minnow
4.26
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
345.35
Hydration Free Energy
-8.6
Log(D) at pH=7.4
0.72
Log(P)
1.59
Log S
-2.64
Log(Vapor Pressure)
-5.91
Melting Point
91.19
pKa Acid
11.83
pKa Basic
4.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9764
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.9449
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.9422
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.9367
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8889
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8880
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8808
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 3 0.8789
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.8770
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8710
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8635
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8581
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8579
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8364
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8310
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8167
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8102
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8043
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8024
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7943
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7936
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7915
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7779
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7760
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7685
Peroxidase C1A P00433 PER1A_ARMRU Armoracia rusticana 2 0.7684
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7637
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7563
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7546
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7519
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7518
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7508
Cyclic nucleotide-binding domain-containing protein E0RR11 E0RR11_SPITD Spirochaeta thermophila 2 0.7492
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7422
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7409
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7396
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 2 0.7383
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7380
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7378
Oxygen-insensitive NAD(P)H nitroreductase P38489 NFSB_ECOLI Escherichia coli 3 0.7364
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7346
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7328
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7326
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7326
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7322
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7318
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7318
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7308
Cyclic nucleotide-gated potassium channel mll3241 Q98GN8 CNGK1_RHILO Mesorhizobium japonicum) 2 0.7293
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7285
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7278
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7270
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7261
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7249
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7237
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7237
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7234
Thymidylate synthase Q4JQW2 TYSY_VZVO Varicella-zoster virus 3 0.7219
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7212
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7210
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7210
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7207
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7204
L-methionine gamma-lyase Q84AR1 Q84AR1_CITFR Citrobacter freundii 3 0.7202
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7200
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7189
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7188
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7180
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7178
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7175
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7169
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7159
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7159
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7148
Catalase-peroxidase Q3JNW6 KATG_BURP1 Burkholderia pseudomallei 2 0.7141
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 2 0.7139
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7132
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7117
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7111
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 2 0.7101
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7100
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7098
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7089
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7089
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 3 0.7083
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7078
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7075
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7075
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7072
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7070
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7062
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7056
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7045
2-hydroxy-6-oxo-6-phenylhexa-2,4-dienoate hydrolase P47229 BPHD_PARXL Paraburkholderia xenovorans 2 0.7045
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7035
Glutamate receptor 3 P19492 GRIA3_RAT Rattus norvegicus 3 0.7033
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7024
D-alanyl-D-alanine carboxypeptidase P15555 DAC_STRSR Streptomyces sp 2 0.7021
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7020
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7018
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7017
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7003
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 2 0.7003
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7002

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