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9 tigloylretronecine
- Family: Plantae - Boraginaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid
| Canonical Smiles | C/C=C(/C(=O)OC1CN2C(C1)C(=CC2)CO)\C |
|---|---|
| InChI | InChI=1S/C13H19NO3/c1-3-9(2)13(16)17-11-6-12-10(8-15)4-5-14(12)7-11/h3-4,11-12,15H,5-8H2,1-2H3/b9-3+ |
| InChIKey | NTPPHLOCCPNXRD-YCRREMRBSA-N |
| Formula | C13H19NO3 |
| HBA | 4 |
| HBD | 1 |
| MW | 237.3 |
| Rotatable Bonds | 3 |
| TPSA | 49.77 |
| LogP | 0.87 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 17 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.62 |
| Exact Mass | 237.14 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Echium setosum | Boraginaceae | Plantae | 2650424 |
Showing of synonyms
9 tigloylretronecine
- El-Shazly A, Sarg T, et al. (1996). Pyrrolizidine alkaloids from Echium setosum and Echium vulgare. Journal of Natural Products,1996,59(3),310-313. [View]
Pubchem:
5352410
No compound-protein relationship available.
SMILES: C1=CCN(C12)CCC2
Level: 0
Mol. Weight: 237.3 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.05
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.44
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.26
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.29
- Plasma Protein Binding
- 17.27
- 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
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.87
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.26
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.02
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 8.3
- 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
- 1.83
- Rat (Acute)
- 2.8
- Rat (Chronic Oral)
- 1.72
- Fathead Minnow
- 4.12
- 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
- 302.07
- Hydration Free Energy
- -9.51
- Log(D) at pH=7.4
- 0.5
- Log(P)
- 0.87
- Log S
- -0.7
- Log(Vapor Pressure)
- -5.07
- Melting Point
- 99.11
- pKa Acid
- 8.48
- pKa Basic
- 8.19
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8337 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8337 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7007 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7007 |