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Terreic acid
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
-
Class: Quinone
- Subclass: Benzoquinone
| Canonical Smiles | O=C1[C@@H]2O[C@@H]2C(=O)C(=C1O)C |
|---|---|
| InChI | InChI=1S/C7H6O4/c1-2-3(8)5(10)7-6(11-7)4(2)9/h6-8H,1H3/t6-,7+/m1/s1 |
| InChIKey | ATFNSNUJZOYXFC-RQJHMYQMSA-N |
| Formula | C7H6O4 |
| HBA | 4 |
| HBD | 1 |
| MW | 154.12 |
| Rotatable Bonds | 0 |
| TPSA | 66.9 |
| LogP | -0.26 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.43 |
| Exact Mass | 154.03 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aspergillus ochraceus | Trichocomaceae | Fungi | 40380 |
Showing of synonyms
Terreic acid
(-)-Terreic Acid
121-40-4
(1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
UNII-XM2Y0DRJ7D
XM2Y0DRJ7D
5,6-Epoxy-3-hydroxy-p-toluquinone
NSC 294734
TERREIC ACID [MI]
NSC-294734
2-Hydroxy-3-methyl-1,4-benzoquinone 5,6-epoxide
(1R)-3-Hydroxy-4-methyl-7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione
DTXSID40879070
Terreate
7-Oxabicyclo(4.1.0)hept-3-ene-2,5-dione, 3-hydroxy-4-methyl-, stereoisomer
Terreic acid (6CI)
(1R,6S)-3-Hydroxy-4-methyl-7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione
(5R),(6S)-EPOXY-3-HYDROXY-P-TOLUQUINONE
3-Hydroxy-4-methyl-7-oxabicyclo(4.1.0)hept-3-ene-2,5-dione
3-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione
DTXCID601017088
NSC294734
(-)-TerreicAcid
BiomolKI_000073
BiomolKI2_000077
SCHEMBL51229
CHEMBL1455300
CHEBI:156546
HMS3267H06
HMS3412M22
HMS3676M22
7-Oxabicyclo(4.1.0)hept-3-ene-2,5-dione, 3-hydroxy-4-methyl-, (1R)-
AKOS006281919
CCG-100677
SMP2_000322
NCGC00025148-02
NCGC00025148-03
DA-59416
NCI60_002449
HY-110013
CS-0032828
(-)-Terreic Acid, Synthetic - CAS 121-40-4
SR-01000597558
SR-01000597558-1
Q27293905
7-Oxabicyclo[4.1.0]hept-3-ene-2, 3-hydroxy-4-methyl-, (1R-cis)-
7-Oxabicyclo[4.1.0]hept-3-ene-2,5-dione,3-hydroxy-4-methyl-,(1R,6S)-
- Attia E, Farouk H, et al. (2020). Antimicrobial and extracellular oxidative enzyme activities of endophytic fungi isolated from alfalfa (Medicago sativa) assisted by metabolic profiling. South African Journal of Botany,2020,134,156-162. [View]
Pubchem:
91437
Cas:
121-40-4
Zinc:
ZINC000100057173
Chebi:
156546
Nmrshiftdb2:
70112175
Chembl:
CHEMBL1455300
Comptox:
DTXSID40879070
CPRiL:
18558
SMILES: C12C(O2)C(=O)C=CC1=O
Level: 0
Mol. Weight: 154.12 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.92
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.12
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.28
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.06
- Plasma Protein Binding
- 3.35
- 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
- Non-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
- 11.99
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.08
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.9
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.91
- 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
- 1.97
- Rat (Acute)
- 2.64
- Rat (Chronic Oral)
- 2.1
- Fathead Minnow
- 3.5
- 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
- 285.94
- Hydration Free Energy
- -10.91
- Log(D) at pH=7.4
- -1.69
- Log(P)
- -0.57
- Log S
- -0.71
- Log(Vapor Pressure)
- -3.95
- Melting Point
- 174.69
- pKa Acid
- 3.56
- pKa Basic
- 1.31
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.9291 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8468 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8434 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7472 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7188 |