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Tenuazonic acid
- Family: Fungi - Pleosporaceae
- Kingdom: Fungi
- Class: Alkaloid
| Canonical Smiles | CCC(C1NC(=O)C(=C1O)C(=O)C)C |
|---|---|
| InChI | InChI=1S/C10H15NO3/c1-4-5(2)8-9(13)7(6(3)12)10(14)11-8/h5,8,13H,4H2,1-3H3,(H,11,14) |
| InChIKey | CEIZFXOZIQNICU-UHFFFAOYSA-N |
| Formula | C10H15NO3 |
| HBA | 3 |
| HBD | 2 |
| MW | 197.23 |
| Rotatable Bonds | 3 |
| TPSA | 66.4 |
| LogP | 0.93 |
| Number Rings | 1 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 14 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.6 |
| Exact Mass | 197.11 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Alternaria species | Pleosporaceae | Fungi | 5598 |
Showing of synonyms
Tenuazonic acid
610-88-8
4-acetyl-2-butan-2-yl-3-hydroxy-1,2-dihydropyrrol-5-one
L-Tenuazonic acid
TENUAZONIC ACID COPPER FROM ALTERNARIA A
76562-67-9
3-Acetyl-5-(sec-butyl)-4-hydroxy-1,5-dihydro-2H-pyrrol-2-one
Vivotoxin
3-(1-hydroxyethylidene)-5-(sec-butyl)pyrrolidine-2,4-dione
Tenuazonic acid copper salt from Alternaria alternata
SCHEMBL8703
SCHEMBL8704
128892-49-9
MLS000863644
610-88-8, free acid
MEGxm0_000289
CHEMBL1362731
CHEMBL2286512
ACon1_000008
DTXSID20926233
MSK7236
GLXC-18188
HMS2270N23
3-Acetyl-5-sec-butyltetramic acid
MFCD00055596
MSK7236-100M
AKOS006282750
NCGC00168879-01
NCGC00168879-02
3-Acetyl-5-sec-butyl-Pyrrole-2,4-diol
SMR000440730
CS-0529988
Tenuazonic acid solution Methanol, 100ug/mL
3-acetyl-5-secbutyl-4-hydroxy-3-pyrrolin-2-one
3-Acetyl-5-sec-butyl-4-hydroxy-L-3-Pyrrolin-2-one
4-Acetyl-2-(butan-2-yl)-5-hydroxy-1,2-dihydro-3H-pyrrol-3-one
2H-Pyrrol-2-one, 3-acetyl-1,5-dihydro-4-hydroxy-5-(1-methylpropyl)-
3-Acetyl-1,5-dihydro-4-hydroxy-5-(1-methylpropyl)-2H-pyrrol-2-one, 9CI
- Aly AH, Ebel R, et al. (2009). Protein kinase inhibitors from the endophytic fungus Alternaria sp. isolated from Polygonum senegalense Growing in Egypt. Planta Medica,2009,75-PE55. [View]
Pubchem:
54678599
Cas:
610-88-8
Gnps:
CCMSLIB00005727818
Nmrshiftdb2:
70006168
Chembl:
CHEMBL1362731
CPRiL:
52656
SMILES: O=C1C=CCN1
Level: 0
Mol. Weight: 197.23 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.0
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.99
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.38
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.23
- Plasma Protein Binding
- 18.21
- 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
- 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
- 4.23
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.58
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.45
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 3.17
- 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
- 2.65
- Rat (Acute)
- 2.05
- Rat (Chronic Oral)
- 2.19
- Fathead Minnow
- 3.54
- 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
- 312.99
- Hydration Free Energy
- -13.07
- Log(D) at pH=7.4
- 0.56
- Log(P)
- 1.31
- Log S
- -1.48
- Log(Vapor Pressure)
- -5.63
- Melting Point
- 97.24
- pKa Acid
- 7.32
- pKa Basic
- 6.54
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.9356 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.9356 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8689 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8689 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8293 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8293 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 3 | 0.8172 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 3 | 0.8172 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7991 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7991 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7816 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7816 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7740 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7740 |
| N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) | Q91XE4 | ACY3_MOUSE | Mus musculus | 3 | 0.7723 |
| N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) | Q91XE4 | ACY3_MOUSE | Mus musculus | 3 | 0.7723 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7526 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7526 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7393 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7393 |
| Putative choline kinase | Q5CUP2 | Q5CUP2_CRYPI | Cryptosporidium parvum | 3 | 0.7248 |
| Putative choline kinase | Q5CUP2 | Q5CUP2_CRYPI | Cryptosporidium parvum | 3 | 0.7248 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7225 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.7225 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7193 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7193 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7160 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7160 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7158 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7158 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7118 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7118 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7093 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7093 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7066 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7066 |