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Dracunculin
- 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
Dracunculin
28843-40-5
6-methoxy-7,8-methylenedioxycoumarin
7,8-Methylenedioxy-6-methoxycoumarin
4-methoxy-[1,3]dioxolo[4,5-h]chromen-8-one
8H-1,3-Dioxolo[4,5-h][1]benzopyran-8-one, 4-methoxy-
4-Methoxy-8H-1,3-dioxolo[4,5-h][1]benzopyran-8-one
4-methoxy-8H-[1,3]dioxolo[4,5-h]chromen-8-one
8RY253KJU4
DTXSID20415753
CHEBI:178386
DB-359702
4-methoxypyrano[6,5-e][1,3]benzodioxol-8-one
4-methoxy-2H,8H-[1,3]dioxolo[4,5-h]chromen-8-one
4-Methoxy-2H,8H-[1,3]dioxolo[4,5-h][1]benzopyran-8-one
- Marco JA, Sanz-Cervera JF, et al. (1997). Sesquiterpene lactones and lignans from Artemisia arborescens.. Phytochemistry,1997,44(6),1133-1137. [View]
Pubchem:
5319474
Cas:
28843-40-5
Zinc:
ZINC000002566154
Chebi:
178386
Nmrshiftdb2:
60023945
Comptox:
DTXSID20415753
No compound-protein relationship available.
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 |