4,7-dimethoxy-5-(prop-2-enyl)benzo-1,3 dioxolan - Compound Card

4,7-dimethoxy-5-(prop-2-enyl)benzo-1,3 dioxolan

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4,7-dimethoxy-5-(prop-2-enyl)benzo-1,3 dioxolan

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenylpropanoid
Canonical Smiles C=CCc1cc(OC)c2c(c1OC)OCO2
InChI InChI=1S/C12H14O4/c1-4-5-8-6-9(13-2)11-12(10(8)14-3)16-7-15-11/h4,6H,1,5,7H2,2-3H3
InChIKey QQRSPHJOOXUALR-UHFFFAOYSA-N
Formula C12H14O4
HBA 4
HBD 0
MW 222.24
Rotatable Bonds 4
TPSA 36.92
LogP 2.16
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 16
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 222.09
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Petroselinum crispum Apiaceae Plantae 4043
2 Apium graveolens Apiaceae Plantae 4045
3 Foeniculum vulgare Apiaceae Plantae 2849586
4 Carum montanum Apiaceae Plantae 1981248

Showing of synonyms

  • Laouer H, Meriem EK, et al. (2009). An antibacterial and antifungal phenylpropanoid from Carum montanum (Coss. et Dur.) Benth. et Hook.. Phytotherapy Research,2009,23,1726-1730. [View] [PubMed]
  • Zoubiri S, Baaliouamer A, et al. (2014). Chemical composition and larvicidal activity of Algerian Foeniculum vulgare seed essential oil. Arabian Journal of Chemistry,2014,7,480-485. [View]
  • MacLeod AJ, MacLeod G, et al. (1988). Volatile aroma constituents of celery. Phytochemistry,1988,27(2),373-375. [View]
  • MacLeod AJ, Snyder CH, et al. (1985). Volatile aroma constituents of parsley leaves. Phytochemistry,1985,24(11),2623-2627. [View]
CPRiL: 230764
Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 222.24 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-4.49
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.98
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.76

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.88
Plasma Protein Binding
36.93
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
5.44
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.74
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.81
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.98
Micronucleos
Safe
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
3.97
Rat (Acute)
2.25
Rat (Chronic Oral)
1.47
Fathead Minnow
4.36
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
302.21
Hydration Free Energy
-5.73
Log(D) at pH=7.4
2.36
Log(P)
3.16
Log S
-2.49
Log(Vapor Pressure)
-3.98
Melting Point
9.56
pKa Acid
9.28
pKa Basic
0.85
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9871
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9871
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9623
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9623
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9042
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9042
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9030
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9030
O-GlcNAcase NagJ Q0TR53 OGA_CLOP1 Clostridium perfringens 3 0.8029
O-GlcNAcase NagJ Q0TR53 OGA_CLOP1 Clostridium perfringens 3 0.8029
Uridine phosphorylase P12758 UDP_ECOLI Escherichia coli 3 0.7965
Uridine phosphorylase P12758 UDP_ECOLI Escherichia coli 3 0.7965
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7942
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7942
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7905
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7905
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7736
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7736
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7619
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7619
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7603
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7603
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7525
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7525
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7521
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7521
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7494
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7494
DNA topoisomerase 1 P06612 TOP1_ECOLI Escherichia coli 3 0.7443
DNA topoisomerase 1 P06612 TOP1_ECOLI Escherichia coli 3 0.7443
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7428
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7428
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7357
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7357
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7343
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7343
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7320
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7320
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7316
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7316
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7292
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7292
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7283
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7283
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7273
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7273
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 2 0.7268
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 2 0.7268
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 2 0.7258
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 2 0.7258
Cell division control protein 42 homolog P60953 CDC42_HUMAN Homo sapiens 2 0.7252
Cell division control protein 42 homolog P60953 CDC42_HUMAN Homo sapiens 2 0.7252
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7243
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7243
L-methionine gamma-lyase P13254 MEGL_PSEPU Pseudomonas putida 3 0.7241
L-methionine gamma-lyase P13254 MEGL_PSEPU Pseudomonas putida 3 0.7241
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 3 0.7233
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 3 0.7233
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7232
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7232
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 2 0.7212
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 2 0.7212
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7195
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7195
Thymidylate kinase Q9KQI2 KTHY_VIBCH Vibrio cholerae serotype O1 3 0.7193
Thymidylate kinase Q9KQI2 KTHY_VIBCH Vibrio cholerae serotype O1 3 0.7193
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7187
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7187
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7185
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7185
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7177
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7177
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7163
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7163
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7161
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7161
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7159
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7159
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7158
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7158
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7156
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7156
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7153
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7153
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7124
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7124
Uridine phosphorylase 2 O95045 UPP2_HUMAN Homo sapiens 3 0.7120
Uridine phosphorylase 2 O95045 UPP2_HUMAN Homo sapiens 3 0.7120
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 2 0.7111
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 2 0.7111
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7110
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7110
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7088
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7088
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7086
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7086
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 2 0.7072
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 2 0.7072
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7069
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7069
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 2 0.7067
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 2 0.7067
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7063
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 2 0.7063
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7059
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7059
Aspartate aminotransferase P00509 AAT_ECOLI Escherichia coli 2 0.7053
Aspartate aminotransferase P00509 AAT_ECOLI Escherichia coli 2 0.7053
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7047
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7047
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 2 0.7041
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 2 0.7041
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 2 0.7034
Poly [ADP-ribose] polymerase 1 P09874 PARP1_HUMAN Homo sapiens 2 0.7034
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7022
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7022
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7022
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7022
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7019
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7019
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7004
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7004

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