Select a section from the left sidebar
Echinatine
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid
| Canonical Smiles | OC1CCN2C1C(=CC2)COC(=O)C(C(O)C)(C(C)C)O |
|---|---|
| InChI | InChI=1S/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3 |
| InChIKey | SFVVQRJOGUKCEG-UHFFFAOYSA-N |
| Formula | C15H25NO5 |
| HBA | 6 |
| HBD | 3 |
| MW | 299.37 |
| Rotatable Bonds | 5 |
| TPSA | 90.23 |
| LogP | -0.33 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 21 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.8 |
| Exact Mass | 299.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Paracaryum rugulosum | Boraginaceae | Plantae | 1288242 |
| 2 | Ageratum conyzoides | Asteraceae | Plantae | 68299 |
Showing of synonyms
Echinatine
MLS002694968
NSC89937
480-83-1
Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, [1S-[1.alpha.,7(2R*,3R*),7a.alpha.]]-
NSC-89937
SCHEMBL16058911
ACon1_001514
BDBM86682
DTXSID60864145
CHEBI:182293
SFVVQRJOGUKCEG-UHFFFAOYSA-N
AAA48083
CAS_114843
NSC_114843
NCGC00180426-01
(7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl)methyl 2-hydroxy-2-(1-hydroxyethyl)-3-methylbutanoate
SMR001560881
XR180165
L000642
BRD-A28796875-001-01-8
(1-Hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl 2,3-dihydroxy-2-isopropylbutanoate #
(1-Hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl 2-hydroxy-2-(1-hydroxyethyl)-3-methylbutanoate
Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, (1S-(1.alpha.,7(2R,3S),7a.alpha.))-
Butanoic acid,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, [1S-(1.alpha.,7(2R,3S),7a.alpha.)]-
Butanoic acid,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, [1S-[1.alpha.,7(2R*,3R*),7a.alpha.]]-
- Belete Y, Wondu K, et al. (2020). Natural Toxins of Ageratum conyzoides from Hepatic Vein Occlusive Disease Affected Community in Ethiopia. Nat Prod Chem Res, 2020, 8(1) ,370. [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]
CPRiL:
42663
SMILES: C1=CCN(C12)CCC2
Level: 0
Mol. Weight: 299.37 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.19
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.7
- 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)
- 0.27
- Plasma Protein Binding
- 7.87
- 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
- 3.46
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.24
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.29
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 8.26
- 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
- 0.8
- Rat (Acute)
- 3.53
- Rat (Chronic Oral)
- 2.19
- Fathead Minnow
- 3.66
- 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
- 340.37
- Hydration Free Energy
- -14.19
- Log(D) at pH=7.4
- 0.19
- Log(P)
- 0.23
- Log S
- -1.05
- Log(Vapor Pressure)
- -7.08
- Melting Point
- 123.73
- pKa Acid
- 6.31
- pKa Basic
- 7.69
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.9096 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.9096 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.8966 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.8966 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8940 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8940 |
| Steroid 17-alpha-hydroxylase/17,20 lyase | P05093 | CP17A_HUMAN | Homo sapiens | 3 | 0.8633 |
| Steroid 17-alpha-hydroxylase/17,20 lyase | P05093 | CP17A_HUMAN | Homo sapiens | 3 | 0.8633 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.8546 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.8546 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.8493 |
| Cytochrome P450 | Q93H81 | Q93H81_STRAX | Streptomyces avermitilis | 3 | 0.8493 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8446 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8446 |
| Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8401 |
| Gag-Pol polyprotein | P0C6F2 | POL_HV1LW | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.8401 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.8261 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.8261 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.8225 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.8225 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8105 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.8105 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8026 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8026 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7949 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7949 |
| Cyclomaltodextrin glucanotransferase | P05618 | CDGT_BACS0 | Bacillus sp | 3 | 0.7929 |
| Cyclomaltodextrin glucanotransferase | P05618 | CDGT_BACS0 | Bacillus sp | 3 | 0.7929 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7903 |
| Methionine aminopeptidase 2 | P9WK19 | MAP12_MYCTU | Mycobacterium tuberculosis | 3 | 0.7903 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7896 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7896 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7886 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7886 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7821 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7821 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7797 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 2 | 0.7797 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7659 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7659 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7624 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7624 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7567 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7567 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7560 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7560 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7498 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7498 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7444 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7444 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7420 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7420 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7406 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7406 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7324 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7324 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7304 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7304 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7294 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7294 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7219 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 2 | 0.7219 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7201 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 2 | 0.7201 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7149 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7149 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7109 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7109 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7092 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7092 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7067 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7067 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7051 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7051 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7050 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7050 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7044 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7044 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7003 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7003 |