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5alpha-chloro-4beta,10alpha-dihydroxy-1alpha,2alpha-epoxy-8alpha-methylbutanoyloxy-11,13-dehydroguaia-6alpha,12-olide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | CCC(C(=O)O[C@H]1C[C@@](C)(O)[C@]23[C@]([C@@H]4[C@@H]1[C@H](C)C(=O)O4)(Cl)[C@@](C[C@@H]3O2)(C)O)C |
|---|---|
| InChI | InChI=1S/C20H29ClO7/c1-6-9(2)15(22)26-11-7-18(5,25)20-12(28-20)8-17(4,24)19(20,21)14-13(11)10(3)16(23)27-14/h9-14,24-25H,6-8H2,1-5H3/t9?,10-,11-,12-,13+,14-,17-,18+,19+,20+/m0/s1 |
| InChIKey | XMNJPMKZYYHSAJ-HELQHENCSA-N |
| Formula | C20H29ClO7 |
| HBA | 7 |
| HBD | 2 |
| MW | 416.9 |
| Rotatable Bonds | 3 |
| TPSA | 105.59 |
| LogP | 1.55 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 28 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.9 |
| Exact Mass | 416.16 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Otanthus maritimus | Asteraceae | Plantae | 1155244 |
Showing of synonyms
5alpha-chloro-4beta,10alpha-dihydroxy-1alpha,2alpha-epoxy-8alpha-methylbutanoyloxy-11,13-dehydroguaia-6alpha,12-olide
- Jakupovic J, Boeker R, et al. (1988). Highly oxygenated guaianolides from Otanthus maritimus. Phytochemistry,1988,27(4),1135-1140. [View]
No compound-protein relationship available.
SMILES: C123C(O3)CCC1C4C(CC(=O)O4)CCC2
Level: 0
Mol. Weight: 416.9 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.11
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.76
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.18
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.31
- Plasma Protein Binding
- 32.94
- 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
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 10.26
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.43
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.06
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 6.35
- 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
- -10.14
- Rat (Acute)
- 4.94
- Rat (Chronic Oral)
- 1.69
- Fathead Minnow
- 3.85
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Toxic
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 400.33
- Hydration Free Energy
- -6.97
- Log(D) at pH=7.4
- 0.94
- Log(P)
- 1.81
- Log S
- -3.09
- Log(Vapor Pressure)
- -7.28
- Melting Point
- 136.85
- pKa Acid
- 5.44
- pKa Basic
- 2.93
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7672 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7672 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7606 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7606 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7580 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7580 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7308 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7308 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7047 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7047 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7024 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7024 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7007 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7007 |