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Wf-3681
- Family: Fungi - Chaetomiaceae
- Kingdom: Fungi
-
Class: Lactone
- Subclass: Butenolide Derivative
| Canonical Smiles | OC(=O)CCC1OC(=O)C(=C1c1ccccc1)O |
|---|---|
| InChI | InChI=1S/C13H12O5/c14-10(15)7-6-9-11(12(16)13(17)18-9)8-4-2-1-3-5-8/h1-5,9,16H,6-7H2,(H,14,15) |
| InChIKey | PPZVSYXNLXFYAD-UHFFFAOYSA-N |
| Formula | C13H12O5 |
| HBA | 4 |
| HBD | 2 |
| MW | 248.23 |
| Rotatable Bonds | 4 |
| TPSA | 83.83 |
| LogP | 1.75 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.23 |
| Exact Mass | 248.07 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Chaetomium sp. | Chaetomiaceae | Fungi | 1769349 |
Showing of synonyms
Wf-3681
WF 3681
105364-56-5
3-(4-hydroxy-5-oxo-3-phenyl-2H-furan-2-yl)propanoic acid
(+-)-2,5-Dihydro-4-hydroxy-5-oxo-3-phenyl-2-furanpropanoic acid
2,5-dihydro-4-hydroxy-5-oxo-3-phenyl-2-furanpropanoic acid
3-(4-hydroxy-5-oxo-3-phenyl-2,5-dihydro-2-furan)propionic acid
MLS000863561
(+-)-WS 3681
MEGxm0_000256
SCHEMBL8904639
CHEMBL1544905
ACon0_001447
ACon1_000871
DTXSID20909465
CHEBI:182217
PPZVSYXNLXFYAD-UHFFFAOYSA-N
HMS2268P16
2-Furanpropanoic acid, 2,5-dihydro-4-hydroxy-5-oxo-3-phenyl-, (+-)-
AKOS022663669
NCGC00169277-01
SMR000440692
HY-155164
NS00097307
3-(4-hydroxy-5-oxo-3-phenyl-2H-uran-2-yl)propanoic acid
3-(4-Hydroxy-5-oxo-3-phenyl-2,5-dihydro-2-furyl)-propionic acid
3-(4-hydroxy-5-oxo-3-phenyl-2,5-dihydro-2-furyl)propionic acid
3-(4-hydroxy-5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)propanoic acid
3-(4-hydroxy-5-oxo-3-phenyl2,5-dihydro-2-furyl)propionic acid
90055-27-9
- Ancheeva E, Küppers L, et al. (2017). Expanding the Metabolic Profile of the Fungus Chaetomium sp. through Co-culture with Autoclaved Pseudomonas aeruginosa. Eur. J. Org. Chem., 2017(22), 3256-3264. [View]
Pubchem:
128356
Cas:
105364-56-5
Gnps:
CCMSLIB00004688095
Chebi:
182217
Nmrshiftdb2:
70104071
Chembl:
CHEMBL1544905
No compound-protein relationship available.
SMILES: C1OC(=O)C=C1c2ccccc2
Level: 1
Mol. Weight: 248.23 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 248.23 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 248.23 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.04
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.66
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.03
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.69
- Plasma Protein Binding
- 14.43
- 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
- Non-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
- 2.26
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -0.79
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.11
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.41
- 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
- 2.64
- Rat (Acute)
- 1.41
- Rat (Chronic Oral)
- 2.34
- Fathead Minnow
- 4.07
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 362.95
- Hydration Free Energy
- -9.05
- Log(D) at pH=7.4
- -1.81
- Log(P)
- 0.56
- Log S
- -1.92
- Log(Vapor Pressure)
- -6.43
- Melting Point
- 161.98
- pKa Acid
- 4.7
- pKa Basic
- 2.68
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Polymerase basic protein 2 | P31345 | PB2_I75A3 | Influenza A virus | 3 | 0.9701 |
| Inosine-5'-monophosphate dehydrogenase | P50097 | IMDH_TRIFO | Tritrichomonas foetus | 3 | 0.9484 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.9367 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.9364 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.9349 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.9233 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.9173 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.9033 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8911 |
| Inosine-5'-monophosphate dehydrogenase | P50097 | IMDH_TRIFO | Tritrichomonas foetus | 3 | 0.8726 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8706 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.8592 |
| cAMP-dependent protein kinase type II-beta regulatory subunit | P12369 | KAP3_RAT | Rattus norvegicus | 3 | 0.8389 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 3 | 0.8340 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.8257 |
| Plasma membrane ATPase | Q42932 | Q42932_NICPL | Nicotiana plumbaginifolia | 3 | 0.8245 |
| Tryptophan synthase alpha chain | P00929 | TRPA_SALTY | Salmonella typhimurium | 4 | 0.8213 |
| Proton-gated ion channel | Q7NDN8 | GLIC_GLOVI | Gloeobacter violaceus | 3 | 0.8198 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 3 | 0.8132 |
| Acidic phospholipase A2 3 | P60045 | PA2A3_NAJSG | Naja sagittifera | 3 | 0.8105 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 3 | 0.8097 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.8035 |
| Gag-Pol polyprotein | P03369 | POL_HV1A2 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7928 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.7913 |
| Tryptophan synthase alpha chain | P00929 | TRPA_SALTY | Salmonella typhimurium | 3 | 0.7883 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.7829 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.7818 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.7788 |
| Single-stranded-DNA-specific exonuclease RecJ | D0EM60 | D0EM60_DEIRD | Deinococcus radiodurans | 3 | 0.7769 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7767 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7741 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 4 | 0.7729 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 3 | 0.7729 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7643 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7589 |
| Unconventional myosin-Va | Q02440 | MYO5A_CHICK | Gallus gallus | 3 | 0.7574 |
| L-methionine gamma-lyase | Q84AR1 | Q84AR1_CITFR | Citrobacter freundii | 3 | 0.7564 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 3 | 0.7544 |
| Nucleoside diphosphate kinase, cytosolic | P22887 | NDKC_DICDI | Dictyostelium discoideum | 3 | 0.7521 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 2 | 0.7501 |
| dTDP-fucosamine acetyltransferase | Q8FBQ3 | WECD_ECOL6 | Escherichia coli O6:H1 | 3 | 0.7492 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.7474 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7428 |
| Adenylate cyclase type 10 | Q96PN6 | ADCYA_HUMAN | Homo sapiens | 3 | 0.7424 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7420 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7411 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 2 | 0.7407 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7388 |
| cAMP-dependent protein kinase type II-beta regulatory subunit | P12369 | KAP3_RAT | Rattus norvegicus | 3 | 0.7383 |
| Snake venom metalloproteinase atrolysin-D | P15167 | VM1AD_CROAT | Crotalus atrox | 3 | 0.7379 |
| Aminopeptidase N | P04825 | AMPN_ECOLI | Escherichia coli | 3 | 0.7369 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7349 |
| Three-prime repair exonuclease 1 | Q91XB0 | TREX1_MOUSE | Mus musculus | 3 | 0.7343 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7342 |
| Cytosol aminopeptidase | P00727 | AMPL_BOVIN | Bos taurus | 2 | 0.7341 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.7314 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7312 |
| 5-formyltetrahydrofolate cyclo-ligase | P75430 | MTHFS_MYCPN | Mycoplasma pneumoniae | 2 | 0.7290 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7284 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 3 | 0.7277 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7247 |
| Metallophosphoesterase MPPED2 | B1WBP0 | MPPD2_RAT | Rattus norvegicus | 3 | 0.7244 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 2 | 0.7242 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 2 | 0.7240 |
| Vascular endothelial growth factor receptor 2 | P35968 | VGFR2_HUMAN | Homo sapiens | 3 | 0.7239 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7233 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7224 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 2 | 0.7224 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 2 | 0.7213 |
| Prostaglandin F2a synthase | Q8I6L9 | Q8I6L9_TRYCR | Trypanosoma cruzi | 2 | 0.7210 |
| Signaling protein | P83820 | P83820_THETH | Thermus thermophilus | 3 | 0.7189 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7187 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7185 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7176 |
| Nucleoside diphosphate kinase | Q5UQL3 | NDK_MIMIV | Acanthamoeba polyphaga mimivirus | 2 | 0.7175 |
| Phospholipase A2 | P00593 | PA21B_BOVIN | Bos taurus | 3 | 0.7171 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 2 | 0.7169 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7154 |
| L-lactate dehydrogenase | Q27743 | LDH_PLAFD | Plasmodium falciparum | 2 | 0.7152 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7150 |
| Glutamate receptor ionotropic, kainate 1 | P22756 | GRIK1_RAT | Rattus norvegicus | 2 | 0.7140 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7140 |
| ATP-dependent helicase/nuclease subunit A | P23478 | ADDA_BACSU | Bacillus subtilis | 2 | 0.7135 |
| Chalcone synthase 2 | P30074 | CHS2_MEDSA | Medicago sativa | 2 | 0.7134 |
| Amino-acid acetyltransferase | Q5FAK7 | Q5FAK7_NEIG1 | Neisseria gonorrhoeae | 2 | 0.7128 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7127 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7125 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 2 | 0.7123 |
| Cysteine synthase | P45040 | CYSK_HAEIN | Haemophilus influenzae | 3 | 0.7119 |
| Agglutinin alpha chain | P18674 | LECA_MACPO | Maclura pomifera | 3 | 0.7117 |
| Lipoprotein E | P26093 | HEL_HAEIN | Haemophilus influenzae | 3 | 0.7094 |
| Acyl-CoA:acyl-CoA alkyltransferase | Q8PDX2 | OLEA_XANCP | Xanthomonas campestris pv. campestris | 3 | 0.7092 |
| 3'-5' exoribonuclease Rv2179c | P9WJ73 | EXRBN_MYCTU | Mycobacterium tuberculosis | 2 | 0.7092 |
| 3-hydroxy-3-methylglutaryl-coenzyme A reductase | P04035 | HMDH_HUMAN | Homo sapiens | 2 | 0.7091 |
| 4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase, chloroplastic | Q9FYS3 | HGGL_SECCE | Secale cereale | 3 | 0.7084 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 2 | 0.7084 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7081 |
| Metallophosphoesterase | A3DJ38 | A3DJ38_HUNT2 | Clostridium thermocellum | 3 | 0.7073 |
| Protein mono-ADP-ribosyltransferase PARP3 | Q9Y6F1 | PARP3_HUMAN | Homo sapiens | 2 | 0.7069 |
| Interleukin enhancer-binding factor 2 | Q9CXY6 | ILF2_MOUSE | Mus musculus | 2 | 0.7056 |
| Nucleoprotein | P13699 | NCAP_LASSJ | Lassa virus | 3 | 0.7050 |
| Diamine acetyltransferase 1 | P21673 | SAT1_HUMAN | Homo sapiens | 2 | 0.7048 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7044 |
| Glutamate dehydrogenase 1, mitochondrial | P00366 | DHE3_BOVIN | Bos taurus | 3 | 0.7038 |
| Type 4 fimbrial biogenesis protein PilM | G3XD28 | G3XD28_PSEAE | Pseudomonas aeruginosa | 3 | 0.7035 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7030 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7027 |
| Phosphatidylinositol 5-phosphate 4-kinase type-2 beta | P78356 | PI42B_HUMAN | Homo sapiens | 3 | 0.7026 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 3 | 0.7019 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7011 |
| Heat shock cognate 71 kDa protein | P19120 | HSP7C_BOVIN | Bos taurus | 3 | 0.7004 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7000 |