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Terretonin
- 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@@]1([C@]2(C)C(=O)C(=C2[C@@]1(C)CCC(=O)C2(C)C)O)O |
|---|---|
| InChI | InChI=1S/C26H32O9/c1-12-11-26(33)22(4)10-9-13(27)21(2,3)15(22)14(28)17(29)24(26,6)16-18(30)35-25(7,20(32)34-8)19(31)23(12,16)5/h16,28,33H,1,9-11H2,2-8H3/t16-,22+,23+,24-,25-,26+/m0/s1 |
| InChIKey | CYHGEJACRPDZDP-RSQIKLETSA-N |
| Formula | C26H32O9 |
| HBA | 9 |
| HBD | 2 |
| MW | 488.53 |
| Rotatable Bonds | 1 |
| TPSA | 144.27 |
| LogP | 2.15 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 35 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.65 |
| Exact Mass | 488.2 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aspergillus terreus | Trichocomaceae | Fungi | 33178 |
Showing of synonyms
Terretonin
71911-90-5
CHEMBL4208768
8795XG0M1T
TERRETONIN, (+)-
UNII-8795XG0M1T
CHEBI:131855
BDBM50459483
HY-N12196
DA-68055
CS-0893271
Q27225281
2H-PHENANTHRO(1,2-C)PYRAN-2-CARBOXYLIC ACID, 1,4,4A,4B,5,7,8,9,10,10A,10B,11,12,12A-TETRADECAHYDRO-6,10B-DIHYDROXY-2,4B,7,7,10A,12A-HEXAMETHYL-12-METHYLENE-1,4,5,8-TETRAOXO-, METHYL ESTER, (2S,4AS,4BR,10AR,10BR,12AS)-
D-HOMO-16-OXAANDROST-5-ENE-17-CARBOXYLIC ACID, 6,9-DIHYDROXY-4,4,8,17-TETRAMETHYL-12-METHYLENE-3,7,15,17A-TETRAOXO-, METHYL ESTER, (17.ALPHA.)-
Methyl (2S,4aS,4bR,10aR,10bR,12aS)-6,10b-dihydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-1,4,4a,4b,5,7,8,9,10,10a,10b,11,12,12a-tetradecahydro-2H-phenanthro[1,2-c]pyran-2-carboxylate
Methyl (2S,4aS,4bR,10aR,10bR,12aS)-6,10b-dihydroxy-2,4b,7,7,10a,12a-hexamethyl-12-methylidene-1,4,5,8-tetraoxo-4a,9,10,11-tetrahydronaphtho[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:
109374149
Cas:
71911-90-5
Zinc:
ZINC000535385303
Chebi:
131855
Nmrshiftdb2:
80003371
Metabolights:
MTBLC131855
Chembl:
CHEMBL4208768
Bindingdb:
50459483
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: 488.53 g/mol
Antibacterial
Absorption
- Caco-2 (logPapp)
- -4.95
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.790
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.29
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.540
- Plasma Protein Binding
- 84.17
- 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
- 4.920
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.280
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.990
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.980
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Toxic
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -120.380
- Rat (Acute)
- 3.520
- Rat (Chronic Oral)
- 2.600
- Fathead Minnow
- 4.000
- 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
- 446.080
- Hydration Free Energy
- -2.470
- Log(D) at pH=7.4
- 1.810
- Log(P)
- 1.27
- Log S
- -4.06
- Log(Vapor Pressure)
- -8.9
- Melting Point
- 273.05
- pKa Acid
- 3.72
- pKa Basic
- 1.5