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6-methylcurvulinic acid
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
- Class: Alkaloid
| Canonical Smiles | OC(=O)Cc1cc(O)c(c(c1C(=O)C)O)C |
|---|---|
| InChI | InChI=1S/C11H12O5/c1-5-8(13)3-7(4-9(14)15)10(6(2)12)11(5)16/h3,13,16H,4H2,1-2H3,(H,14,15) |
| InChIKey | RLDOSQILCSICAK-UHFFFAOYSA-N |
| Formula | C11H12O5 |
| HBA | 4 |
| HBD | 3 |
| MW | 224.21 |
| Rotatable Bonds | 3 |
| TPSA | 94.83 |
| LogP | 1.24 |
| Number Rings | 1 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 16 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.27 |
| Exact Mass | 224.07 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Penicillium citrinum | Trichocomaceae | Fungi | 5077 |
| 2 | Penicillium sp | Trichocomaceae | Fungi | 5081 |
Showing of synonyms
6-methylcurvulinic acid
2-(2-acetyl-3,5-dihydroxy-4-methylphenyl)acetic acid
6-Methylcurvulinate
2-(2-Acetyl-3,5-dihydroxy-4-methylphenyl)acetate
CHEMBL2385864
CHEBI:221073
- El-Neketi M, Ebrahim W, et al. (2013). Alkaloids and polyketides from Penicillium citrinum, an endophyte isolated from the Moroccan plant Ceratonia siliqua. Journal of Natural Products,2013,76(6),1099-1104. [View] [PubMed]
- Orfali R, Aly A, et al. (2015). Isochroman and isocoumarin derivatives from hypersaline lake sediment-derived fungus Penicillium sp. Phytochemistry Letters, 2015,13,234–238. [View]
No compound-protein relationship available.
SMILES: c1ccccc1
Level: 0
Mol. Weight: 224.21 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.22
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.97
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.56
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.53
- Plasma Protein Binding
- 24.36
- 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
- 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
- 11.94
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -0.17
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.98
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.0
- 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
- 4.93
- Rat (Acute)
- 1.76
- Rat (Chronic Oral)
- 3.11
- Fathead Minnow
- 3.89
- 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
- 354.67
- Hydration Free Energy
- -11.32
- Log(D) at pH=7.4
- -0.82
- Log(P)
- 1.83
- Log S
- -1.49
- Log(Vapor Pressure)
- -7.04
- Melting Point
- 169.12
- pKa Acid
- 5.11
- pKa Basic
- 7.63
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.9276 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.9276 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.9243 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.9243 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9208 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9208 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.9197 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.9197 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.9151 |
| Biflaviolin synthase CYP158A1 | Q9KZF5 | C1581_STRCO | Streptomyces coelicolor / M145) | 3 | 0.9151 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.9147 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 3 | 0.9147 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8832 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8832 |
| Glycogen phosphorylase, liver form | P06737 | PYGL_HUMAN | Homo sapiens | 3 | 0.8741 |
| Glycogen phosphorylase, liver form | P06737 | PYGL_HUMAN | Homo sapiens | 3 | 0.8741 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8698 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8698 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8595 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8595 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8541 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8541 |
| DNA polymerase III subunit epsilon | P03007 | DPO3E_ECOLI | Escherichia coli | 3 | 0.8540 |
| DNA polymerase III subunit epsilon | P03007 | DPO3E_ECOLI | Escherichia coli | 3 | 0.8540 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8483 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8483 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8231 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8231 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8206 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8206 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 3 | 0.8189 |
| 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase | Q81LL4 | MTNN_BACAN | Bacillus anthracis | 3 | 0.8189 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.8153 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.8153 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.8128 |
| Toxoflavin degrading enzyme | E3SET7 | E3SET7_PAEPO | Paenibacillus polymyxa | 3 | 0.8128 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8032 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8032 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8009 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8009 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.7966 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.7966 |
| Aromatic-amino-acid aminotransferase | P95468 | TYRB_PARDE | Paracoccus denitrificans | 3 | 0.7928 |
| Aromatic-amino-acid aminotransferase | P95468 | TYRB_PARDE | Paracoccus denitrificans | 3 | 0.7928 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7878 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP8 | DEOD_ECOLI | Escherichia coli | 3 | 0.7878 |
| Achbp | I6L8L2 | I6L8L2_CAPTE | Capitella teleta | 3 | 0.7838 |
| Achbp | I6L8L2 | I6L8L2_CAPTE | Capitella teleta | 3 | 0.7838 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7795 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7795 |
| 3-dehydroquinate dehydratase | P9WPX7 | AROQ_MYCTU | Mycobacterium tuberculosis | 3 | 0.7789 |
| 3-dehydroquinate dehydratase | P9WPX7 | AROQ_MYCTU | Mycobacterium tuberculosis | 3 | 0.7789 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7745 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7745 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 2 | 0.7724 |
| Tetracycline repressor protein class H | P51561 | TETR8_PASMD | Pasteurella multocida | 2 | 0.7724 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7717 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.7717 |
| TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase | Q6T1W8 | FDTA_ANETH | Aneurinibacillus thermoaerophilus | 3 | 0.7714 |
| TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase | Q6T1W8 | FDTA_ANETH | Aneurinibacillus thermoaerophilus | 3 | 0.7714 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7709 |
| Gag-Pol polyprotein | P03366 | POL_HV1B1 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7709 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7676 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7676 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7666 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7666 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7636 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7636 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7601 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 3 | 0.7601 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7599 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7599 |
| Flavin reductase like domain-containing protein | Q4UKE8 | Q4UKE8_RICFE | Rickettsia felis | 3 | 0.7577 |
| Flavin reductase like domain-containing protein | Q4UKE8 | Q4UKE8_RICFE | Rickettsia felis | 3 | 0.7577 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7549 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7549 |
| Aspartate aminotransferase | P00509 | AAT_ECOLI | Escherichia coli | 3 | 0.7512 |
| Aspartate aminotransferase | P00509 | AAT_ECOLI | Escherichia coli | 3 | 0.7512 |
| Aspartokinase 1, chloroplastic | Q9LYU8 | AK1_ARATH | Arabidopsis thaliana | 3 | 0.7488 |
| Aspartokinase 1, chloroplastic | Q9LYU8 | AK1_ARATH | Arabidopsis thaliana | 3 | 0.7488 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 2 | 0.7467 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 2 | 0.7467 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.7435 |
| Polymerase acidic protein | Q5EP34 | Q5EP34_9INFA | Influenza A virus | 3 | 0.7435 |
| Phospholipase A2 | P00593 | PA21B_BOVIN | Bos taurus | 3 | 0.7426 |
| Phospholipase A2 | P00593 | PA21B_BOVIN | Bos taurus | 3 | 0.7426 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.7374 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.7374 |
| Flavin-dependent thymidylate synthase | Q9WYT0 | THYX_THEMA | Thermotoga maritima | 3 | 0.7365 |
| Flavin-dependent thymidylate synthase | Q9WYT0 | THYX_THEMA | Thermotoga maritima | 3 | 0.7365 |
| 4-hydroxyphenylacetate 3-monooxygenase, reductase component | Q5SJP7 | HPAC_THET8 | Thermus thermophilus | 3 | 0.7358 |
| 4-hydroxyphenylacetate 3-monooxygenase, reductase component | Q5SJP7 | HPAC_THET8 | Thermus thermophilus | 3 | 0.7358 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7330 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7330 |
| AGAP003309-PA | A0A1U7F4W2 | A0A1U7F4W2_ANOGA | Anopheles gambiae | 3 | 0.7295 |
| AGAP003309-PA | A0A1U7F4W2 | A0A1U7F4W2_ANOGA | Anopheles gambiae | 3 | 0.7295 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7285 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7285 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7264 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7264 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7260 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7260 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7258 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7258 |
| orotidine-5'-phosphate decarboxylase | Q8T6J6 | Q8T6J6_PLAFA | Plasmodium falciparum | 4 | 0.7228 |
| orotidine-5'-phosphate decarboxylase | Q8T6J6 | Q8T6J6_PLAFA | Plasmodium falciparum | 4 | 0.7228 |
| Nucleoside diphosphate kinase A 2 | P52175 | NDKA2_BOVIN | Bos taurus | 3 | 0.7200 |
| Nucleoside diphosphate kinase A 2 | P52175 | NDKA2_BOVIN | Bos taurus | 3 | 0.7200 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7123 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7123 |
| Casein kinase II subunit alpha' | P19784 | CSK22_HUMAN | Homo sapiens | 2 | 0.7077 |
| Casein kinase II subunit alpha' | P19784 | CSK22_HUMAN | Homo sapiens | 2 | 0.7077 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7077 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7077 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 4 | 0.7045 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 4 | 0.7045 |
| Serine--pyruvate aminotransferase | Q7PRG3 | Q7PRG3_ANOGA | Anopheles gambiae | 3 | 0.7027 |
| UDP-galactopyranose mutase | Q48485 | GLF1_KLEPN | Klebsiella pneumoniae | 3 | 0.7027 |
| Serine--pyruvate aminotransferase | Q7PRG3 | Q7PRG3_ANOGA | Anopheles gambiae | 3 | 0.7027 |
| UDP-galactopyranose mutase | Q48485 | GLF1_KLEPN | Klebsiella pneumoniae | 3 | 0.7027 |
| cGMP-dependent protein kinase 1 | P00516 | KGP1_BOVIN | Bos taurus | 3 | 0.7026 |
| cGMP-dependent protein kinase 1 | P00516 | KGP1_BOVIN | Bos taurus | 3 | 0.7026 |
| uroporphyrinogen-III C-methyltransferase | P95417 | P95417_PSEAI | Pseudomonas aeruginosa | 3 | 0.7022 |
| uroporphyrinogen-III C-methyltransferase | P95417 | P95417_PSEAI | Pseudomonas aeruginosa | 3 | 0.7022 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7014 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7014 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7005 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7005 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7002 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7002 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7001 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.7001 |