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Tanzawaic acid B
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
- Class: Carboxylic Acid
| Canonical Smiles | C[C@H]1C[C@@H](C)[C@H]2[C@H](C1)C=C[C@@H]([C@@H]2/C=C/C=C/C(=O)O)C |
|---|---|
| InChI | InChI=1S/C18H26O2/c1-12-10-14(3)18-15(11-12)9-8-13(2)16(18)6-4-5-7-17(19)20/h4-9,12-16,18H,10-11H2,1-3H3,(H,19,20)/b6-4+,7-5+/t12-,13-,14+,15-,16-,18-/m0/s1 |
| InChIKey | DUGGXGNWQZWAAS-RAJPTAFASA-N |
| Formula | C18H26O2 |
| HBA | 1 |
| HBD | 1 |
| MW | 274.4 |
| Rotatable Bonds | 3 |
| TPSA | 37.3 |
| LogP | 4.3 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 20 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.61 |
| Exact Mass | 274.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Penicillium citrinum | Trichocomaceae | Fungi | 5077 |
Showing of synonyms
Tanzawaic acid B
CHEMBL3353037
SCHEMBL16712870
CHEBI:198373
BDBM50036279
HY-N12914
CS-1054553
(2E,4E)-5-[(1S,2S,4aR,6S,8R,8aS)-2,6,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]penta-2,4-dienoic acid
Pubchem:
102331593
Zinc:
ZINC000136588171
Nmrshiftdb2:
70019045
Chembl:
CHEMBL3353037
Bindingdb:
50036279
No compound-protein relationship available.
SMILES: C1=CCCC(C12)CCCC2
Level: 0
Mol. Weight: 274.4 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.59
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.57
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.44
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.99
- Plasma Protein Binding
- 80.38
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- 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
- -0.25
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.96
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.6
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.03
- Micronucleos
- Safe
- 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
- Toxic
- T. Pyriformis
- 1.73
- Rat (Acute)
- 2.46
- Rat (Chronic Oral)
- 2.05
- Fathead Minnow
- 3.93
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 350.41
- Hydration Free Energy
- -5.17
- Log(D) at pH=7.4
- 2.55
- Log(P)
- 5.27
- Log S
- -4.91
- Log(Vapor Pressure)
- -5.77
- Melting Point
- 161.9
- pKa Acid
- 5.94
- pKa Basic
- 6.48
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8844 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8844 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 3 | 0.8065 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 3 | 0.8065 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.8029 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.8029 |
| Abscisic acid receptor PYL10 | Q8H1R0 | PYL10_ARATH | Arabidopsis thaliana | 3 | 0.8015 |
| Abscisic acid receptor PYL10 | Q8H1R0 | PYL10_ARATH | Arabidopsis thaliana | 3 | 0.8015 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 3 | 0.7851 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 3 | 0.7851 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7824 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7824 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7788 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7788 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7595 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7595 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7584 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7584 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7562 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7562 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7482 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7482 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7459 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7459 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7405 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7405 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7391 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7391 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7386 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7386 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7321 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7321 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7320 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7320 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7291 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7291 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7262 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7262 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7213 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7213 |
| Jasmonoyl--L-amino acid synthetase JAR1 | Q9SKE2 | JAR1_ARATH | Arabidopsis thaliana | 3 | 0.7203 |
| Jasmonoyl--L-amino acid synthetase JAR1 | Q9SKE2 | JAR1_ARATH | Arabidopsis thaliana | 3 | 0.7203 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7163 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7163 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7149 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7149 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7134 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7134 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7127 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7127 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7110 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7110 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7101 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7101 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7100 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7100 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7096 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7096 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7086 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7086 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7058 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 2 | 0.7058 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7049 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7049 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7044 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7044 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7002 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7002 |