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16-hydroxybutenolide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Labdane Diterpenoid
| Canonical Smiles | O=C1C=C(C(O1)O)CCC1C(=C)CCC2C1(C)CCCC2(C)C(=O)O |
|---|---|
| InChI | InChI=1S/C20H28O5/c1-12-5-8-15-19(2,9-4-10-20(15,3)18(23)24)14(12)7-6-13-11-16(21)25-17(13)22/h11,14-15,17,22H,1,4-10H2,2-3H3,(H,23,24) |
| InChIKey | GZTUAPFQPZVTGA-UHFFFAOYSA-N |
| Formula | C20H28O5 |
| HBA | 4 |
| HBD | 2 |
| MW | 348.44 |
| Rotatable Bonds | 4 |
| TPSA | 83.83 |
| LogP | 3.43 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.7 |
| Exact Mass | 348.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Conyza stricta | Asteraceae | Plantae | 3122715 |
Showing of synonyms
16-hydroxybutenolide
16-Hydroxy-8(17),13-
Labdadien-15,16-olid-19-oic acid
Compound NP-025149
RCB00985
AKOS040736856
Pubchem:
14287152
No compound-protein relationship available.
SMILES: C1CCCC(C12)CCC(=C)C2CCC3=CC(=O)OC3
Level: 1
Mol. Weight: 348.44 g/mol
SMILES: C=C(C1)CCC(C12)CCCC2
Level: 0
Mol. Weight: 348.44 g/mol
SMILES: O=C1C=CCO1
Level: 0
Mol. Weight: 348.44 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.9
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.91
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.8
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.16
- Plasma Protein Binding
- 26.32
- 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
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 1.24
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.56
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -1.1
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.01
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- 0.61
- Rat (Acute)
- 3.2
- Rat (Chronic Oral)
- 2.31
- Fathead Minnow
- 4.01
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 398.31
- Hydration Free Energy
- -5.57
- Log(D) at pH=7.4
- 0.71
- Log(P)
- 2.95
- Log S
- -4.26
- Log(Vapor Pressure)
- -8.08
- Melting Point
- 174.43
- pKa Acid
- 4.33
- pKa Basic
- 6.96
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.9896 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.9896 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.9224 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 3 | 0.9224 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.9057 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.9057 |
| Deacetoxycephalosporin C synthase | P18548 | CEFE_STRCL | Streptomyces clavuligerus | 3 | 0.8375 |
| Deacetoxycephalosporin C synthase | P18548 | CEFE_STRCL | Streptomyces clavuligerus | 3 | 0.8375 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.8371 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.8371 |
| Branched-chain-amino-acid aminotransferase, mitochondrial | O15382 | BCAT2_HUMAN | Homo sapiens | 3 | 0.8273 |
| Branched-chain-amino-acid aminotransferase, mitochondrial | O15382 | BCAT2_HUMAN | Homo sapiens | 3 | 0.8273 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.8034 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.8034 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7813 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7813 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7796 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7796 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7746 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7746 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7718 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7718 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7646 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7646 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7623 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7623 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7548 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7548 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7537 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7537 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7532 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7532 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7500 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7500 |
| Steroid 17-alpha-hydroxylase/17,20 lyase | P05093 | CP17A_HUMAN | Homo sapiens | 2 | 0.7498 |
| Steroid 17-alpha-hydroxylase/17,20 lyase | P05093 | CP17A_HUMAN | Homo sapiens | 2 | 0.7498 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7462 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 2 | 0.7462 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7450 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7450 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7439 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7439 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 2 | 0.7439 |
| Retinol-binding protein 4 | P18902 | RET4_BOVIN | Bos taurus | 2 | 0.7439 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7430 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7430 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7396 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7396 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 2 | 0.7332 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 2 | 0.7332 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7322 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7322 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7294 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7294 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7290 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7290 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7253 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7253 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 2 | 0.7246 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 2 | 0.7246 |
| Gibberellin receptor GID1 | Q6L545 | GID1_ORYSJ | Oryza sativa subsp. japonica | 3 | 0.7227 |
| Gibberellin receptor GID1 | Q6L545 | GID1_ORYSJ | Oryza sativa subsp. japonica | 3 | 0.7227 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7220 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7220 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7198 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7198 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7191 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 2 | 0.7191 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7191 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 2 | 0.7191 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7165 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7165 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 2 | 0.7162 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 2 | 0.7162 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7107 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7107 |
| N-acetyltransferase domain-containing protein | Q9HV14 | Q9HV14_PSEAE | Pseudomonas aeruginosa | 3 | 0.7091 |
| N-acetyltransferase domain-containing protein | Q9HV14 | Q9HV14_PSEAE | Pseudomonas aeruginosa | 3 | 0.7091 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7065 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7065 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7042 |
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.7042 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7037 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 2 | 0.7037 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7031 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7031 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7012 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7012 |