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7-tigloylretronecine
- Family: Plantae - Boraginaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid
| Canonical Smiles | C/C(=C\C)/C(=O)O[C@@H]1CCN2[C@@H]1C(=CC2)CO |
|---|---|
| InChI | InChI=1S/C13H19NO3/c1-3-9(2)13(16)17-11-5-7-14-6-4-10(8-15)12(11)14/h3-4,11-12,15H,5-8H2,1-2H3/b9-3+/t11-,12-/m1/s1 |
| InChIKey | TYGYPIIOOQNWBU-UHTQEIBISA-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 | Alkanna orientalis | Boraginaceae | Plantae | 543563 |
| 2 | Alkanna orientalis | Boraginaceae | Plantae | 543563 |
| 3 | Alkanna orientalis | Boraginaceae | Plantae | 543563 |
Showing of synonyms
7-tigloylretronecine
((1R,8R)-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-1-yl) (E)-2-methylbut-2-enoate
[(1R,8R)-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-1-yl] (E)-2-methylbut-2-enoate
136094-34-3
Tygypiiooqnwbu-uhtqeibisa-n
- Roeder E, Sarg T, et al. (1992). Pyrrolizidine alkaloids from Alkanna orientalis. Fitoterapia,1992,63(5),405-408. [View]
- Hammouda FM, Ismail SI, et al. (1992). Pyrrolizidine alkaloids from alkanna orientalis (L.) Boiss. Qatar University Science Journal,1992,12,80-82. [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]
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)
- -5.02
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.41
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.58
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.22
- Plasma Protein Binding
- 22.0
- 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
- 5.36
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.48
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.16
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.41
- 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
- 0.77
- Rat (Acute)
- 3.31
- Rat (Chronic Oral)
- 1.63
- Fathead Minnow
- 4.02
- 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
- 300.47
- Hydration Free Energy
- -9.79
- Log(D) at pH=7.4
- 0.38
- Log(P)
- 0.98
- Log S
- -0.88
- Log(Vapor Pressure)
- -5.33
- Melting Point
- 119.79
- pKa Acid
- 8.54
- pKa Basic
- 8.07
| 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 | 0.8856 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.8856 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8352 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8352 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.8045 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.8045 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7862 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7862 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7490 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7490 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7447 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7447 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.7355 |
| Transcriptional activator, LuxR/UhpA family of regulators | Q7NQP7 | Q7NQP7_CHRVO | Chromobacterium violaceum | 3 | 0.7355 |
| Muconolactone Delta-isomerase | Q8G9L0 | Q8G9L0_RHOOP | Rhodococcus opacus | 2 | 0.7176 |
| Muconolactone Delta-isomerase | Q8G9L0 | Q8G9L0_RHOOP | Rhodococcus opacus | 2 | 0.7176 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.7038 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.7038 |