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Retroisosenine
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid
| Canonical Smiles | O=C1O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]2(O[C@](C1)(C)C[C@H]2C)C |
|---|---|
| InChI | InChI=1S/C18H25NO5/c1-11-8-17(2)9-14(20)23-13-5-7-19-6-4-12(15(13)19)10-22-16(21)18(11,3)24-17/h4,11,13,15H,5-10H2,1-3H3/t11-,13-,15-,17-,18+/m1/s1 |
| InChIKey | KOYQLXLYMDNSGL-DZHCQNFQSA-N |
| Formula | C18H25NO5 |
| HBA | 6 |
| HBD | 0 |
| MW | 335.4 |
| Rotatable Bonds | 0 |
| TPSA | 65.07 |
| LogP | 1.43 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.78 |
| Exact Mass | 335.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Solanecio angulatus | Asteraceae | Plantae | 1670880 |
| 2 | Solanecio mannii | Asteraceae | Plantae | — |
| 3 | Solanecio tuberosus var. tuberosus | Asteraceae | Plantae | 189251 |
| 4 | Crotalaria gillettii | Leguminosae/Fabaceae | Plantae | 1132206 |
Showing of synonyms
Retroisosenine
62018-78-4
R2J24LT8Y2
(1R,5R,7R,8S,18R)-5,7,8-trimethyl-2,10,19-trioxa-15-azatetracyclo[10.5.1.15,8.015,18]nonadec-12-ene-3,9-dione
(4R,6R,7S,15aR,15bR)-4,5,6,7,10,12,14,15,15a,15b-Decahydro-4,6,7-trimethyl-4,7-epoxy-2H-[1,6]dioxacyclotridecino[2,3,4-gh]pyrrolizine-2,8(3H)-dione
4,7-Epoxy-2H-[1,6]dioxacyclotridecino[2,3,4-gh]pyrrolizine-2,8(3H)-dione, 4,5,6,7,10,12,14,15,15a,15b-decahydro-4,6,7-trimethyl-, (4R,6R,7S,15aR,15bR)-
(1R,5R,7R,8S,18R)-5,7,8-trimethyl-2,10,19-trioxa-15-azatetracyclo(10.5.1.15,8.015,18)nonadec-12-ene-3,9-dione
(4R,6R,7S,15aR,15bR)-4,5,6,7,10,12,14,15,15a,15b-Decahydro-4,6,7-trimethyl-4,7-epoxy-2H-(1,6)dioxacyclotridecino(2,3,4-gh)pyrrolizine-2,8(3H)-dione
4,7-Epoxy-2H-(1,6)dioxacyclotridecino(2,3,4-gh)pyrrolizine-2,8(3H)-dione, 4,5,6,7,10,12,14,15,15a,15b-decahydro-4,6,7-trimethyl-, (4R,6R,7S,15aR,15bR)-
Koyqlxlymdnsgl-wbozigavsa-n
UNII-R2J24LT8Y2
CHEMBL452758
AKOS040753737
- Asres K, Sporer F, et al. (2008). Occurrence of pyrrolizidine alkaloids in three Ethiopian Solanecio species. Biochemical Systematics and Ecology,2008,36(5-6),399-407. [View] [PubMed]
- Asres K, Sporer F, et al. (2004). Patterns of pyrrolizidine alkaloids in 12 Ethiopian Crotalaria species.. Biochemical systematics and ecology,2004,32(10),915-930. [View] [PubMed]
No compound-protein relationship available.
SMILES: C1CN2CCC(C2C=13)OC(=O)CC4CCC(O4)C(=O)OC3
Level: 0
Mol. Weight: 335.4 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.74
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.95
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.37
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.56
- Plasma Protein Binding
- 25.93
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.31
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.89
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.32
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.96
- 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
- -2.16
- Rat (Acute)
- 3.6
- Rat (Chronic Oral)
- 1.45
- Fathead Minnow
- 3.81
- 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
- 371.55
- Hydration Free Energy
- -5.16
- Log(D) at pH=7.4
- 1.02
- Log(P)
- 1.13
- Log S
- -2.74
- Log(Vapor Pressure)
- -6.86
- Melting Point
- 161.21
- pKa Acid
- 7.37
- pKa Basic
- 6.62
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8176 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.8176 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7873 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7873 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7858 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.7858 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7740 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7740 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7654 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7654 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7614 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7614 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7445 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7445 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7408 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7408 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7401 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7401 |
| FKBP-type peptidyl-prolyl cis-trans isomerase FkpA | P45523 | FKBA_ECOLI | Escherichia coli | 4 | 0.7378 |
| FKBP-type peptidyl-prolyl cis-trans isomerase FkpA | P45523 | FKBA_ECOLI | Escherichia coli | 4 | 0.7378 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 2 | 0.7326 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 2 | 0.7326 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 4 | 0.7266 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 4 | 0.7266 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7264 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7264 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7183 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7183 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 2 | 0.7158 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 2 | 0.7158 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7154 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7154 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7128 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7128 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 4 | 0.7127 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 4 | 0.7127 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7070 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7070 |