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Chaetobutenolide C
- Family: Fungi - Chaetomiaceae
- Kingdom: Fungi
-
Class: Lactone
- Subclass: Butenolide Derivative
| Canonical Smiles | COC1(CCC(=O)O)OC(=O)C(=C1c1ccccc1)O |
|---|---|
| InChI | InChI=1S/C14H14O6/c1-19-14(8-7-10(15)16)11(12(17)13(18)20-14)9-5-3-2-4-6-9/h2-6,17H,7-8H2,1H3,(H,15,16) |
| InChIKey | JIJNZYGKBCXMOO-UHFFFAOYSA-N |
| Formula | C14H14O6 |
| HBA | 5 |
| HBD | 2 |
| MW | 278.26 |
| Rotatable Bonds | 5 |
| TPSA | 93.06 |
| LogP | 1.72 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.29 |
| Exact Mass | 278.08 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Chaetomium sp. | Chaetomiaceae | Fungi | 1769349 |
Showing of synonyms
Chaetobutenolide C
- 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:
132608436
No compound-protein relationship available.
SMILES: C1OC(=O)C=C1c2ccccc2
Level: 1
Mol. Weight: 278.26 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 278.26 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 278.26 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.15
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.840
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.42
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.700
- Plasma Protein Binding
- 6.09
- 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
- 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
- 2.500
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -0.370
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.200
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.920
- 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
- 3.690
- Rat (Acute)
- 1.630
- Rat (Chronic Oral)
- 2.870
- Fathead Minnow
- 4.110
- 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
- 369.130
- Hydration Free Energy
- -10.370
- Log(D) at pH=7.4
- -1.160
- Log(P)
- 0.25
- Log S
- -1.8
- Log(Vapor Pressure)
- -7.17
- Melting Point
- 145.86
- pKa Acid
- 4.33
- pKa Basic
- 3.84
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Snake venom metalloproteinase atrolysin-D | P15167 | VM1AD_CROAT | Crotalus atrox | 3 | 0.9391 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 3 | 0.9211 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 3 | 0.9042 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 3 | 0.8637 |
| cAMP-dependent protein kinase type II-beta regulatory subunit | P12369 | KAP3_RAT | Rattus norvegicus | 3 | 0.8511 |
| L-lactate dehydrogenase A chain | P13491 | LDHA_RABIT | Oryctolagus cuniculus | 3 | 0.8447 |
| Pyridoxal kinase, putative | C4LVZ4 | C4LVZ4_ENTHI | Entamoeba histolytica | 3 | 0.8441 |
| N-terminal acetyltransferase A complex subunit NAT1 | P12945 | NAT1_YEAST | Saccharomyces cerevisiae | 3 | 0.8384 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.8357 |
| Plasma membrane ATPase | Q42932 | Q42932_NICPL | Nicotiana plumbaginifolia | 3 | 0.8341 |
| Single-stranded-DNA-specific exonuclease RecJ | D0EM60 | D0EM60_DEIRD | Deinococcus radiodurans | 3 | 0.8324 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8217 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.8171 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.8032 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8000 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.7970 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7788 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7751 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.7698 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7692 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7625 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.7605 |
| Nucleoside diphosphate kinase, cytosolic | P22887 | NDKC_DICDI | Dictyostelium discoideum | 3 | 0.7601 |
| D-alanyl-D-alanine carboxypeptidase | P15555 | DAC_STRSR | Streptomyces sp | 3 | 0.7564 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7503 |
| Mitochondrial dynamics protein MIEF1 | Q9NQG6 | MID51_HUMAN | Homo sapiens | 2 | 0.7486 |
| Hydroxymethylglutaryl-CoA synthase | Q9FD71 | HMGCS_ENTFL | Enterococcus faecalis | 2 | 0.7458 |
| dTDP-fucosamine acetyltransferase | Q8FBQ3 | WECD_ECOL6 | Escherichia coli O6:H1 | 3 | 0.7420 |
| AcsD | Q93AT8 | Q93AT8_DICCH | Dickeya chrysanthemi | 3 | 0.7382 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7382 |
| CCA-adding enzyme | O28126 | CCA_ARCFU | Archaeoglobus fulgidus | 2 | 0.7370 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7368 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.7359 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7354 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.7321 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7310 |
| 5-formyltetrahydrofolate cyclo-ligase | P75430 | MTHFS_MYCPN | Mycoplasma pneumoniae | 2 | 0.7308 |
| Cysteine synthase | P45040 | CYSK_HAEIN | Haemophilus influenzae | 3 | 0.7298 |
| Inosine-5'-monophosphate dehydrogenase | P50097 | IMDH_TRIFO | Tritrichomonas foetus | 3 | 0.7295 |
| Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 2 | 0.7289 |
| Cytidine and deoxycytidylate deaminase zinc-binding region | Q82Y41 | Q82Y41_NITEU | Nitrosomonas europaea | 3 | 0.7285 |
| Egl nine homolog 1 | Q9GZT9 | EGLN1_HUMAN | Homo sapiens | 3 | 0.7272 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7264 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 2 | 0.7256 |
| Adenylate cyclase type 10 | Q96PN6 | ADCYA_HUMAN | Homo sapiens | 3 | 0.7253 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 2 | 0.7226 |
| Cytosol aminopeptidase | P00727 | AMPL_BOVIN | Bos taurus | 2 | 0.7220 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 3 | 0.7200 |
| Glutamate dehydrogenase 1, mitochondrial | P00366 | DHE3_BOVIN | Bos taurus | 3 | 0.7198 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 2 | 0.7186 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 3 | 0.7162 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7152 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7141 |
| Protocatechuate 3,4-dioxygenase beta chain | P00437 | PCXB_PSEPU | Pseudomonas putida | 2 | 0.7128 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7099 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.7084 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7069 |
| Anthranilate phosphoribosyltransferase | P50384 | TRPD_SACS2 | Saccharolobus solfataricus | 2 | 0.7063 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.7052 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 2 | 0.7048 |
| Vanillate porin OpdK | Q9HUR5 | Q9HUR5_PSEAE | Pseudomonas aeruginosa | 2 | 0.7043 |
| Class B acid phosphatase | Q540U1 | APHA_SALTM | Salmonella typhimurium | 2 | 0.7038 |
| 6-phosphogluconate dehydrogenase, decarboxylating | P96789 | 6PGD_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7037 |
| Nucleoside 2-deoxyribosyltransferase | Q8RLY5 | Q8RLY5_LACHE | Lactobacillus helveticus | 2 | 0.7034 |
| L-lactate dehydrogenase | Q27743 | LDH_PLAFD | Plasmodium falciparum | 2 | 0.7023 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7017 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7008 |