Dillapiole - Compound Card

Dillapiole

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Dillapiole

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Monoaromatic
    • Subclass: Benzodioxole
Canonical Smiles C=CCc1cc2OCOc2c(c1OC)OC
InChI InChI=1S/C12H14O4/c1-4-5-8-6-9-11(16-7-15-9)12(14-3)10(8)13-2/h4,6H,1,5,7H2,2-3H3
InChIKey LIKYNOPXHGPMIH-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 Daucus carota subsp. maritimus Apiaceae Plantae 126355
2 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]
  • Jabrane A, Ben Jannet H, et al. (2009). Flower and root oils of the Tunisian Daucus carota L. ssp. maritimus (Apiaceae): integrated analyses by GC, GC/MS, and 13C-NMR spectroscopy, and in vitro antibacterial activity.. Chemistry and Biodiversity,2009,6(6),881-889. [View] [PubMed]
Pubchem: 10231
Kegg Ligand: C10449
Chebi: 70453
Nmrshiftdb2: 60031232
Metabolights: MTBLC70453
Bindingdb: 50242106
CPRiL: 116029
Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 222.24 g/mol

Antibacterial
Antimicrobial

Absorption

Caco-2 (logPapp)
-4.47
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.0
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.67

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.93
Plasma Protein Binding
34.87
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
5.82
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.73
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.77
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.2
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
3.91
Rat (Acute)
2.26
Rat (Chronic Oral)
1.48
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
302.05
Hydration Free Energy
-5.78
Log(D) at pH=7.4
2.19
Log(P)
2.98
Log S
-2.38
Log(Vapor Pressure)
-3.96
Melting Point
9.52
pKa Acid
9.39
pKa Basic
1.03
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 0.9869
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.9869
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9473
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.9473
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9426
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.9426
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9070
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9070
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9002
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9002
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8231
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8231
O-GlcNAcase NagJ Q0TR53 OGA_CLOP1 Clostridium perfringens 3 0.7988
O-GlcNAcase NagJ Q0TR53 OGA_CLOP1 Clostridium perfringens 3 0.7988
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7841
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7841
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7583
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7583
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7555
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7555
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7542
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7542
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7499
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7499
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7485
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7485
LL-diaminopimelate aminotransferase, chloroplastic Q93ZN9 DAPAT_ARATH Arabidopsis thaliana 2 0.7482
LL-diaminopimelate aminotransferase, chloroplastic Q93ZN9 DAPAT_ARATH Arabidopsis thaliana 2 0.7482
DNA topoisomerase 1 P06612 TOP1_ECOLI Escherichia coli 3 0.7388
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7388
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7388
DNA topoisomerase 1 P06612 TOP1_ECOLI Escherichia coli 3 0.7388
Cysteine desulfurase IscS 2 O29689 ISCS2_ARCFU Archaeoglobus fulgidus 2 0.7349
Cysteine desulfurase IscS 2 O29689 ISCS2_ARCFU Archaeoglobus fulgidus 2 0.7349
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7317
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7317
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7315
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7315
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7309
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7309
Aspartate aminotransferase, mitochondrial P00508 AATM_CHICK Gallus gallus 2 0.7308
Aspartate aminotransferase, mitochondrial P00508 AATM_CHICK Gallus gallus 2 0.7308
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7289
Ferric enterobactin-binding periplasmic protein FepB P0AEL6 FEPB_ECOLI Escherichia coli 3 0.7289
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 3 0.7282
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 3 0.7282
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7282
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7282
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7274
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 2 0.7274
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7271
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 2 0.7271
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7269
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7269
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7258
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7258
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7249
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7249
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7243
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7243
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7216
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7216
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7213
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 2 0.7213
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 3 0.7208
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 3 0.7208
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7207
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7207
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7206
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7206
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7204
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7204
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7196
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7196
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7192
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7192
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7185
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7185
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7182
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7182
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7178
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7178
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 2 0.7171
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 2 0.7171
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7169
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7169
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7160
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7160
Thymidylate kinase Q9KQI2 KTHY_VIBCH Vibrio cholerae serotype O1 3 0.7159
Thymidylate kinase Q9KQI2 KTHY_VIBCH Vibrio cholerae serotype O1 3 0.7159
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7145
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7145
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7140
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7140
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7138
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7138
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7133
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7133
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7127
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7127
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 3 0.7126
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 3 0.7126
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7124
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7124
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7123
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7123
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7121
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7121
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7121
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7121
Uridine phosphorylase 2 O95045 UPP2_HUMAN Homo sapiens 3 0.7111
Uridine phosphorylase 2 O95045 UPP2_HUMAN Homo sapiens 3 0.7111
Uridine phosphorylase P12758 UDP_ECOLI Escherichia coli 3 0.7111
Uridine phosphorylase P12758 UDP_ECOLI Escherichia coli 3 0.7111
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7092
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7092
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7077
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7077
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 2 0.7071
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7071
Anthranilate phosphoribosyltransferase P9WFX5 TRPD_MYCTU Mycobacterium tuberculosis 2 0.7071
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7071
Nucleoside phosphorylase, putative Q57VZ2 Q57VZ2_TRYB2 Trypanosoma brucei brucei 3 0.7050
Nucleoside phosphorylase, putative Q57VZ2 Q57VZ2_TRYB2 Trypanosoma brucei brucei 3 0.7050
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 2 0.7045
3-hydroxybenzoate 4-monooxygenase Q6SSJ6 MOBA_COMTE Comamonas testosteroni 2 0.7045
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7040
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7040
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7040
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7040
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7036
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7036
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7031
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7031
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7020
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7020
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7015
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7015
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7010
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7010
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7002
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7002

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