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Haageanolide
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Sesquiterpene Lactone
| Canonical Smiles | C/C/1=C/[C@H]2OC(=O)C(=C)[C@@H]2C[C@@H](/C(=C\CC1)/C)O |
|---|---|
| InChI | InChI=1S/C15H20O3/c1-9-5-4-6-10(2)13(16)8-12-11(3)15(17)18-14(12)7-9/h6-7,12-14,16H,3-5,8H2,1-2H3/b9-7-,10-6-/t12-,13-,14+/m0/s1 |
| InChIKey | CHKPFVHCBRAVJP-RSBQXGOBSA-N |
| Formula | C15H20O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 248.32 |
| Rotatable Bonds | 0 |
| TPSA | 46.53 |
| LogP | 2.52 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 18 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.53 |
| Exact Mass | 248.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Brocchia cinerea | Asteraceae | Plantae | 282208 |
| 2 | Pluchea dioscoridis | Asteraceae | Plantae | — |
Showing of synonyms
Haageanolide
- Jakupovic J, Aal MA, et al. (1988). Further glaucolides and other sesquiterpene lactones from Brocchia cinerea.. Phytochemistry,1988,27(7),2219-2224. [View]
- Dawidar AA, Metwally M (1985). New alpha-cyclocostunolide and isocostic acid derivatives from Pluchea dioscoridis. Chemical and Pharmaceutical Bulletin,1985,33(11),5068-5070. [View]
Pubchem:
101316961
No compound-protein relationship available.
SMILES: C=C1C(=O)OC(C12)C=CCCC=CCC2
Level: 0
Mol. Weight: 248.32 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.82
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.23
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.64
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.49
- Plasma Protein Binding
- 45.82
- 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
- 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
- 7.12
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.07
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.34
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 4.1
- 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
- 0.64
- Rat (Acute)
- 2.32
- Rat (Chronic Oral)
- 1.91
- Fathead Minnow
- 3.99
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Toxic
General Properties
- Boiling Point
- 322.51
- Hydration Free Energy
- -7.17
- Log(D) at pH=7.4
- 1.87
- Log(P)
- 2.42
- Log S
- -2.99
- Log(Vapor Pressure)
- -5.48
- Melting Point
- 92.77
- pKa Acid
- 9.13
- pKa Basic
- 5.39
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.8259 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.8259 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.8062 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.8062 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8038 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8038 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7489 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 2 | 0.7489 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7280 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7280 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7194 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7194 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 3 | 0.7174 |
| Abscisic acid receptor PYL9 | Q84MC7 | PYL9_ARATH | Arabidopsis thaliana | 3 | 0.7174 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7134 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7134 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 2 | 0.7132 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 2 | 0.7132 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7074 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7074 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 2 | 0.7060 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 2 | 0.7060 |