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9-senecioylretronecine
- Family: Plantae - Boraginaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid
| Canonical Smiles | CC(=CC(=O)OCC1=CCN2[C@H]1[C@H](O)CC2)C |
|---|---|
| InChI | InChI=1S/C13H19NO3/c1-9(2)7-12(16)17-8-10-3-5-14-6-4-11(15)13(10)14/h3,7,11,13,15H,4-6,8H2,1-2H3/t11-,13-/m1/s1 |
| InChIKey | ILQKJOOWZFSMTN-DGCLKSJQSA-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 |
| 2 | Echium humile | Boraginaceae | Plantae | 161689 |
| 3 | Alkanna orientalis | Boraginaceae | Plantae | 543563 |
Showing of synonyms
9-senecioylretronecine
ILQKJOOWZFSMTN-DGCLKSJQSA-N
DTXSID201126138
88205-11-2
[(1R,7aR)-2,3,5,7a-Tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl 3-methyl-2-butenoate
- 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]
- El-Shazly A, El-Domiaty M, et al. (1998). Pyrrolizidine alkaloids in members of the Boraginaceae from Sinai (Egypt). Biochemical Systematics and Ecology,1998,26(6),619-636. [View]
- El-Shazly A, Sarg T, et al. (1996). Pyrrolizidine and tetrahydroisoquinoline alkaloids from Echium humile. Phytochemistry,1996,42(1),225-230. [View]
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)
- -5.14
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.4
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.69
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.24
- Plasma Protein Binding
- 22.03
- 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
- 6.28
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.27
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.08
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 7.53
- 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
- 0.27
- Rat (Acute)
- 3.58
- Rat (Chronic Oral)
- 1.75
- Fathead Minnow
- 3.87
- 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
- 308.58
- Hydration Free Energy
- -10.06
- Log(D) at pH=7.4
- 0.84
- Log(P)
- 0.83
- Log S
- -0.87
- Log(Vapor Pressure)
- -5.63
- Melting Point
- 107.11
- pKa Acid
- 7.97
- pKa Basic
- 7.87
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.9017 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.9017 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8651 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.8651 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8483 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8483 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8396 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8396 |
| Cyclomaltodextrin glucanotransferase | P05618 | CDGT_BACS0 | Bacillus sp | 3 | 0.7893 |
| Cyclomaltodextrin glucanotransferase | P05618 | CDGT_BACS0 | Bacillus sp | 3 | 0.7893 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7779 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7779 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7367 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7367 |
| Lysosomal acid glucosylceramidase | P04062 | GLCM_HUMAN | Homo sapiens | 3 | 0.7278 |
| Lysosomal acid glucosylceramidase | P04062 | GLCM_HUMAN | Homo sapiens | 3 | 0.7278 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 3 | 0.7277 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 3 | 0.7277 |
| Angiotensin-converting enzyme | Q10714 | ACE_DROME | Drosophila melanogaster | 3 | 0.7143 |
| Angiotensin-converting enzyme | Q10714 | ACE_DROME | Drosophila melanogaster | 3 | 0.7143 |