Dracunculin - Compound Card

Dracunculin

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Dracunculin

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Coumarin
Canonical Smiles COc1cc2ccc(=O)oc2c2c1OCO2
InChI InChI=1S/C11H8O5/c1-13-7-4-6-2-3-8(12)16-9(6)11-10(7)14-5-15-11/h2-4H,5H2,1H3
InChIKey GHIKZCCKJTXOGO-UHFFFAOYSA-N
Formula C11H8O5
HBA 5
HBD 0
MW 220.18
Rotatable Bonds 1
TPSA 57.9
LogP 1.53
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 16
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 220.04
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia arborescens Asteraceae Plantae 72386

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1997). Sesquiterpene lactones and lignans from Artemisia arborescens.. Phytochemistry,1997,44(6),1133-1137. [View]

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)ccc3c2oc(=O)cc3

Level: 0

Mol. Weight: 220.18 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.54
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.030
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.34

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.100
Plasma Protein Binding
60.45
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
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.800
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.110
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.290
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.620
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
4.060
Rat (Acute)
2.310
Rat (Chronic Oral)
1.480
Fathead Minnow
4.380
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
365.790
Hydration Free Energy
-8.580
Log(D) at pH=7.4
1.500
Log(P)
1.86
Log S
-3.05
Log(Vapor Pressure)
-5.47
Melting Point
165.48
pKa Acid
5.94
pKa Basic
0.17
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9802
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9802
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9461
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9461
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9372
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9372
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9329
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9329
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9315
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9315
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9262
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.9262
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9259
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.9259
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9036
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9036
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8815
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8815
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8787
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8787
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8733
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8733
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8588
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8588
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8419
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8419
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.8233
Achbp I6L8L2 I6L8L2_CAPTE Capitella teleta 3 0.8233
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8208
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8208
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8133
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8133
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8047
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.8047
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7953
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7953
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7820
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 2 0.7820
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 2 0.7726
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 2 0.7726
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7627
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7627
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7618
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7618
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7591
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7591
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7571
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7571
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7570
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7570
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7532
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7532
O-GlcNAcase NagJ Q0TR53 OGA_CLOP1 Clostridium perfringens 3 0.7528
O-GlcNAcase NagJ Q0TR53 OGA_CLOP1 Clostridium perfringens 3 0.7528
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7527
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7527
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7522
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7522
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7507
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7507
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7461
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7461
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7460
cGMP-dependent protein kinase 1 P00516 KGP1_BOVIN Bos taurus 3 0.7460
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7453
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7453
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7440
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7440
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7427
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7427
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7414
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7414
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 3 0.7412
Nucleoside permease Q9KPL5 Q9KPL5_VIBCH Vibrio cholerae serotype O1 3 0.7412
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7407
Uncharacterized protein Q3F0V8 Q3F0V8_BACTI Bacillus thuringiensis serovar israelensis ATCC 35646 3 0.7407
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7364
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7364
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7362
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7362
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7361
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7361
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 2 0.7340
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 2 0.7340
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7337
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7337
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7327
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7327
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7276
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7276
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7249
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7249
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7243
D-mycarose 3-C-methyltransferase Q194Q4 Q194Q4_STRAA Streptomyces argillaceus 4 0.7243
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7231
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7231
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7222
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7222
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7217
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7217
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7216
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7216
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7208
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7208
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7206
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7206
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7206
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7206
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 2 0.7168
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 2 0.7168
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7160
tRNA (adenine(9)-N1)-methyltransferase Q4J894 TRM10_SULAC Sulfolobus acidocaldarius 3 0.7160
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7154
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7154
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7150
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7150
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7150
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7150
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7140
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7140
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7136
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7136
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7113
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7113
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7086
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7086
Thymidylate kinase Q9KQI2 KTHY_VIBCH Vibrio cholerae serotype O1 3 0.7076
Thymidylate kinase Q9KQI2 KTHY_VIBCH Vibrio cholerae serotype O1 3 0.7076
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7030
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 2 0.7030
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7022
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7022
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7021
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7021
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7013
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7013
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7002
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7002

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