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Echimidine N-oxide
- Family: Plantae - Boraginaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid
| Canonical Smiles | C/C=C(\C(=O)O[C@@H]1CCN2(=O)[C@@H]1C(=CC2)COC(=O)[C@](C(O)(C)C)([C@@H](O)C)O)/C |
|---|---|
| InChI | InChI=1S/C20H31NO8/c1-6-12(2)17(23)29-15-8-10-21(27)9-7-14(16(15)21)11-28-18(24)20(26,13(3)22)19(4,5)25/h6-7,13,15-16,22,25-26H,8-11H2,1-5H3/b12-6-/t13-,15+,16+,20-,21?/m0/s1 |
| InChIKey | KDJGEXAPDZNXSD-KCFAIRMISA-N |
| Formula | C20H31NO8 |
| HBA | 8 |
| HBD | 3 |
| MW | 413.47 |
| Rotatable Bonds | 7 |
| TPSA | 136.35 |
| LogP | 0.32 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 29 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.7 |
| Exact Mass | 413.2 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Echium confusum | Boraginaceae | Plantae | 21610 |
Showing of synonyms
Echimidine N-oxide
DTXSID501345822
41093-89-4
[(7R,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl]methyl (2R)-2,3-dihydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
((7R,8R)-7-((Z)-2-methylbut-2-enoyl)oxy-4-oxido-5,6,7,8-tetrahydro-3H-pyrrolizin-4-ium-1-yl)methyl (2R)-2,3-dihydroxy-2-((1S)-1-hydroxyethyl)-3-methylbutanoate
DTXCID201774486
2-Butenoic acid, 2-methyl-, 7-((2,3-dihydroxy-2-(1-hydroxyethyl)-3-methyl-1-oxobutoxyl)methyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester, N-oxide
111-226-5
(1R,7aR)-7-((((R)-2,3-Dihydroxy-2-((S)-1-hydroxyethyl)-3-methylbutanoyl)oxy)methyl)-1-(((Z)-2-methylbut-2-enoyl)oxy)-1,2,3,4,5,7a-hexahydropyrrolizine 4-oxide
CHEMBL2269157
HY-N9513
AKOS040758120
Echimidine-N-oxide 100 microg/mL in Water
CS-0182701
NS00067007
No compound-protein relationship available.
SMILES: C1C=CC(N12=O)CCC2
Level: 0
Mol. Weight: 413.47 g/mol
Anti-acetylcholinesterase
Absorption
- Caco-2 (logPapp)
- -5.34
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -4.94
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.42
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.44
- Plasma Protein Binding
- 53.62
- 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
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.4
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.82
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.46
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.16
- 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
- -10.24
- Rat (Acute)
- 3.55
- Rat (Chronic Oral)
- 2.2
- Fathead Minnow
- 3.97
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 375.91
- Hydration Free Energy
- -9.94
- Log(D) at pH=7.4
- 0.14
- Log(P)
- -0.95
- Log S
- -1.23
- Log(Vapor Pressure)
- -8.4
- Melting Point
- 173.81
- pKa Acid
- 4.57
- pKa Basic
- 3.7
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Integrin alpha-L | P20701 | ITAL_HUMAN | Homo sapiens | 3 | 0.8739 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8625 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 4 | 0.8088 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.7853 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7594 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 3 | 0.7573 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7502 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.7471 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7467 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7378 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7369 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7303 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7241 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7217 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7211 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7194 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 2 | 0.7181 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7092 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7006 |