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Terretonin A
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
-
Class: Terpenoid
- Subclass: Tetracyclic Meroterpenoid
| Canonical Smiles | COC(=O)[C@]1(C)OC(=O)[C@@H]2[C@](C1=O)(C)C(=C)C[C@H]1[C@@]2(C)C(=O)C(=C2[C@]1(C)CCC(=O)C2(C)C)O |
|---|---|
| InChI | InChI=1S/C26H32O8/c1-12-11-13-23(4)10-9-14(27)22(2,3)16(23)15(28)18(29)25(13,6)17-19(30)34-26(7,21(32)33-8)20(31)24(12,17)5/h13,17,28H,1,9-11H2,2-8H3/t13-,17-,23-,24+,25-,26-/m1/s1 |
| InChIKey | GTEJJXOFLPCZGJ-DOFPOEDPSA-N |
| Formula | C26H32O8 |
| HBA | 8 |
| HBD | 1 |
| MW | 472.53 |
| Rotatable Bonds | 1 |
| TPSA | 124.04 |
| LogP | 3.04 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 472.21 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aspergillus terreus | Trichocomaceae | Fungi | 33178 |
Showing of synonyms
Terretonin A
Methyl (2R,4aS,4bR,10aR,10bR,12aR)-6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-9,10,10b,11-tetrahydro-4aH-naphtho[1,2-h]isochromene-2-carboxylate
865092-86-0
Methyl (1R,2S,5R,7R,10R,11R)-17-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,18-tetraoxo-4-oxatetracyclo(8.8.0.0,.0,)octadec-16-ene-5-carboxylic acid
Methyl (1R,2S,5R,7R,10R,11R)-17-hydroxy-1,5,7,11,15,15-hexamethyl-8-methylidene-3,6,14,18-tetraoxo-4-oxatetracyclo[8.8.0.0,.0,]octadec-16-ene-5-carboxylic acid
Methyl (2R,4aS,4bR,10aR,10bR,12aR)-6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-9,10,10b,11-tetrahydro-4aH-naphtho(1,2-h)isochromene-2-carboxylate
CHEMBL470042
CHEBI:200476
BDBM50478873
DA-58418
Methyl (2S,4aR,4bS,10aS,10bS,12aS)-6-hydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-9,10,10b,11-tetrahydro-4aH-naphtho[1,2-h]isochromene-2-carboxylate
- Chen H, Daletos G, et al. (2015). Inducing secondary metabolite production by the soil-dwelling fungus Aspergillus terreus through bacterial co-culture. Phytochemistry Letters,2015,12,35-41. [View]
Pubchem:
11547355
Cas:
865092-86-0
Zinc:
ZINC000034637515
Nmrshiftdb2:
70004141
Chembl:
CHEMBL470042
Bindingdb:
50478873
No compound-protein relationship available.
SMILES: O=C1OCC(=O)C(C(=C)C2)C1C(C(=O)C3)C2C(C=34)CCC(=O)C4
Level: 0
Mol. Weight: 472.53 g/mol
Antibacterial
Absorption
- Caco-2 (logPapp)
- -4.8
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.810
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.73
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.970
- Plasma Protein Binding
- 92.0
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-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
- Substrate
- OATP1B1
- Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.060
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.930
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.810
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.960
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -84.080
- Rat (Acute)
- 3.020
- Rat (Chronic Oral)
- 1.990
- Fathead Minnow
- 4.050
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 446.410
- Hydration Free Energy
- -2.450
- Log(D) at pH=7.4
- 2.410
- Log(P)
- 1.99
- Log S
- -4.76
- Log(Vapor Pressure)
- -8.47
- Melting Point
- 291.76
- pKa Acid
- 4.71
- pKa Basic
- 1.16