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Terrien
- Family: Fungi - Trichocomaceae
- Kingdom: Fungi
-
Class: Lactone
- Subclass: Cyclopentenone Analogue
| Canonical Smiles | C/C=C/C1=CC(=O)[C@@H]([C@H]1O)O |
|---|---|
| InChI | InChI=1S/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8-/m0/s1 |
| InChIKey | MHOOPNKRBMHHEC-HZIBQTDNSA-N |
| Formula | C8H10O3 |
| HBA | 3 |
| HBD | 2 |
| MW | 154.16 |
| Rotatable Bonds | 1 |
| TPSA | 57.53 |
| LogP | -0.21 |
| Number Rings | 1 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.38 |
| Exact Mass | 154.06 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Aspergillus terreus | Trichocomaceae | Fungi | 33178 |
| 2 | Aspergillus flavipes | Trichocomaceae | Fungi | 41900 |
Showing of synonyms
Terrien
Terrein
582-46-7
(+)-TERREIN
(+)Terrein
(4S,5R)-4,5-dihydroxy-3-[(E)-prop-1-enyl]cyclopent-2-en-1-one
3I47HPE16N
(4S,5R)-4,5-Dihydroxy-3-((E)-prop-1-en-1-yl)cyclopent-2-enone
UNII-3I47HPE16N
NSC-291308
NSC 291308
2-Cyclopenten-1-one, 4,5-dihydroxy-3-propenyl-
CHEMBL506722
MEGxm0_000160
SCHEMBL1884980
ACon1_001984
MHOOPNKRBMHHEC-HZIBQTDNSA-
2-Cyclopenten-1-one, 4,5-dihydroxy-3-(1-propenyl)-, (4S-(3(E),4.alpha.,5.beta.))-
CHEBI:177543
DTXSID101017469
GLXC-15930
MFCD09752761
AKOS006327725
NCGC00179945-01
DA-58416
HY-119808
CS-0078056
AB-131/42300811
4,5-dihydroxy-3-(1-propenyl)-2-cyclopenten-1-one
BRD-K68034638-001-01-1
Q27257243
(4S,5R)-4,5-Dihydroxy-3-((E)-prop-1-en-1-yl)cyclopent-2-en-1-one
(4S,5R)-4,5-dihydroxy-3-(1E)-1-propen-1-yl-2-cyclopenten-1-one
2-Cyclopenten-1-one, 4,5-dihydroxy-3-(1E)-1-propenyl-, (4S,5R)-
2-Cyclopenten-1-one, 4,5-dihydroxy-3-(1-propenyl)-, (4S-(3(E),4alpha,5beta))-
2-CYCLOPENTEN-1-ONE, 4,5-DIHYDROXY-3-(1E)-1-PROPEN-1-YL-, (4S,5R)-
InChI=1/C8H10O3/c1-2-3-5-4-6(9)8(11)7(5)10/h2-4,7-8,10-11H,1H3/b3-2+/t7-,8-/m0/s1
- Nagia MM, El-Metwally MM, et al. (2012). Four butyrolactones and diverse bioactive secondary metabolites from terrestrial Aspergillus flavipes MM2: isolation and structure determination. Organic and Medicinal Chemistry Letters,2012,2(1),9. [View] [PubMed]
- 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:
6436830
Cas:
582-46-7
Zinc:
ZINC000100020097
Chebi:
177543
Nmrshiftdb2:
20212870
Chembl:
CHEMBL506722
CPRiL:
70472
SMILES: O=C1C=CCC1
Level: 0
Mol. Weight: 154.16 g/mol
Antibacterial
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.68
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.25
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.9
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.29
- Plasma Protein Binding
- 26.24
- 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
- 4.4
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -0.21
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.68
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 3.66
- 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
- Safe
- T. Pyriformis
- 0.5
- Rat (Acute)
- 1.71
- Rat (Chronic Oral)
- 2.4
- Fathead Minnow
- 3.81
- 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
- 283.19
- Hydration Free Energy
- -14.18
- Log(D) at pH=7.4
- -0.28
- Log(P)
- -0.14
- Log S
- -0.49
- Log(Vapor Pressure)
- -5.74
- Melting Point
- 127.78
- pKa Acid
- 6.86
- pKa Basic
- 3.47
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7889 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7889 |
| Raucaffricine-O-beta-D-glucosidase | Q9SPP9 | RG1_RAUSE | Rauvolfia serpentina | 3 | 0.7591 |
| Raucaffricine-O-beta-D-glucosidase | Q9SPP9 | RG1_RAUSE | Rauvolfia serpentina | 3 | 0.7591 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7532 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7532 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7333 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 2 | 0.7333 |
| Alpha/beta hydrolase fold protein | D2J2T6 | D2J2T6_9RHIZ | Ochrobactrum sp. T63 | 3 | 0.7300 |
| Alpha/beta hydrolase fold protein | D2J2T6 | D2J2T6_9RHIZ | Ochrobactrum sp. T63 | 3 | 0.7300 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 3 | 0.7223 |
| Phosphotriesterase | Q5KZU5 | Q5KZU5_GEOKA | Geobacillus kaustophilus | 3 | 0.7223 |
| Regulatory protein SdiA | P07026 | SDIA_ECOLI | Escherichia coli | 3 | 0.7095 |
| Regulatory protein SdiA | P07026 | SDIA_ECOLI | Escherichia coli | 3 | 0.7095 |