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Loliolide
- Family: Plantae - Asteraceae
- Kingdom: Plantae, Chromista
-
Class: Terpenoid
- Subclass: Monoterpene Lactone
| Canonical Smiles | O[C@@H]1C[C@@]2(C)OC(=O)C=C2C(C1)(C)C |
|---|---|
| InChI | InChI=1S/C11H16O3/c1-10(2)5-7(12)6-11(3)8(10)4-9(13)14-11/h4,7,12H,5-6H2,1-3H3/t7-,11+/m0/s1 |
| InChIKey | XEVQXKKKAVVSMW-WRWORJQWSA-N |
| Formula | C11H16O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 196.25 |
| Rotatable Bonds | 0 |
| TPSA | 46.53 |
| LogP | 1.41 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 14 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.73 |
| Exact Mass | 196.11 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Amberboa tubuliflora | Asteraceae | Plantae | 1284450 |
| 2 | Cladostephus spongiosus f. verticillatus | Sphacelariaceae | Chromista | 74470 |
| 3 | Cheirolophus intybaceus | Asteraceae | Plantae | 64995 |
| 4 | Otanthus maritimus | Asteraceae | Plantae | 1155244 |
| 5 | Xanthium pungens | Asteraceae | Plantae | 1979456 |
Showing of synonyms
Loliolide
Loliolid
5989-02-6
(-)-loliolide
Digiprolactone
CAULILIDE
U3BB4IM281
1,3-Dihydroxy-3,5,5-trimethylcyclohexylidene-4-acetic acid lactone
LOLIOLIDE, (-)-
UNII-U3BB4IM281
(6S,7AR)-LOLIOLIDE
DTXSID501019112
NSC 289632
NSC-289632
LOLIOLIDE (B712568K091)
2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-6-hydroxy-4,4,7a-trimethyl-, (6S-cis)-
2(4H)-BENZOFURANONE, 5,6,7,7A-TETRAHYDRO-6-HYDROXY-4,4,7A-TRIMETHYL-, (6S,7AR)-
DTXCID801477117
2(4H)-BENZOFURANONE, 5,6,7,7A-TETRAHYDRO-6beta-HYDROXY-4,4,7Abeta-TRIMETHYL-
Calendin
(3S,5R)-Loliolide
CHEBI:69774
(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-1-benzofuran-2-one
2(4H)-Benzofuranone,5,6,7,7a-tetrahydro-6-hydroxy-4,4,7a-trimethyl-, (6S,7aR)-
SCHEMBL789415
CHEMBL227113
XEVQXKKKAVVSMW-WRWORJQWSA-N
BDBM50463330
AKOS030231291
FS-7957
HY-118020A
NCGC00385365-01
DA-54994
XC176134
CS-0137966
Q27138116
(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-6,7-dihydro-5H-benzofuran-2-one
(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-5,6,7,7a-tetrahydrobenzofuran-2(4H)-one
2(4H)-BENZOFURANONE, 5,6,7,7A-TETRAHYDRO-6.BETA.-HYDROXY-4,4,7A.BETA.-TRIMETHYL-
NCGC00385365-01_C11H16O3_2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-6-hydroxy-4,4,7a-trimethyl-, (6S,7aR)-
- Ahmed AA, El-Ela MA, et al. (1990). A guaianolide from Amberboa tubuliflora. Phytochemistry,1990,29(12),3946-3947. [View]
- El Hattab M, Culioli G, et al. (2008). Apo-fucoxanthinoids and loliolide from the brown alga Cladostephus spongiosus f. verticillatus (Heterokonta, Sphacelariales). Biochemical Systematics and Ecology,2008,36(5-6),447-451. [View]
- Jakupovic J, Boeker R, et al. (1988). Highly oxygenated guaianolides from Otanthus maritimus. Phytochemistry,1988,27(4),1135-1140. [View]
- Ahmed AA, Jakupovic J, et al. (1990). Sesquiterpene lactones from Xanthium pungens. Phytochemistry,1990,29(7),2211-2215. [View]
- Marco JA, Sanz-Cervera JF, et al. (1994). Sesquiterpene lactones, lignans and aromatic esters ftrom Cheirolophus species. Phytochemistry,1994,37(4),1101-1107. [View]
Pubchem:
100332
Cas:
5989-02-6
Gnps:
CCMSLIB00000852205
Zinc:
ZINC000001565391
Chebi:
69774
Nmrshiftdb2:
60018836
Metabolights:
MTBLC69774
Chembl:
CHEMBL227113
Bindingdb:
50463330
CPRiL:
61339
SMILES: C1C(=O)OC(C=12)CCCC2
Level: 0
Mol. Weight: 196.25 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.79
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.03
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.74
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.24
- Plasma Protein Binding
- 28.86
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- 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
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 6.81
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.42
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.35
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.04
- 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
- -1.3
- Rat (Acute)
- 1.85
- Rat (Chronic Oral)
- 1.53
- Fathead Minnow
- 3.58
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 270.4
- Hydration Free Energy
- -6.12
- Log(D) at pH=7.4
- 1.19
- Log(P)
- 0.5
- Log S
- -1.5
- Log(Vapor Pressure)
- -2.58
- Melting Point
- 88.06
- pKa Acid
- 9.7
- pKa Basic
- 4.95
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7475 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7475 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7221 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7221 |