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Retronecine
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid
| Canonical Smiles | OCC1=CCN2[C@H]1[C@H](O)CC2 |
|---|---|
| InChI | InChI=1S/C8H13NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h1,7-8,10-11H,2-5H2/t7-,8-/m1/s1 |
| InChIKey | HJSJELVDQOXCHO-HTQZYQBOSA-N |
| Formula | C8H13NO2 |
| HBA | 3 |
| HBD | 2 |
| MW | 155.2 |
| Rotatable Bonds | 1 |
| TPSA | 43.7 |
| LogP | -0.65 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.75 |
| Exact Mass | 155.09 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Trichodesma africanum | Boraginaceae | Plantae | 379304 |
| 2 | Echium setosum | Boraginaceae | Plantae | 2650424 |
| 3 | Anchusa milleri | Boraginaceae | Plantae | 256477 |
| 4 | Anchusa hispida | Boraginaceae | Plantae | 170551 |
| 5 | Lappula spinocarpos | Boraginaceae | Plantae | 1245804 |
| 6 | Crotalaria pycnostachya | Leguminosae/Fabaceae | Plantae | 1670847 |
Showing of synonyms
Retronecine
480-85-3
(+)-Retronecine
CCRIS 5776
(1r,7ar)-7-(hydroxymethyl)-2,3,5,7a-tetrahydro-1h-pyrrolizin-1-ol
HSDB 3567
(1R,8R)-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-1-ol
2P5723M6II
RETRONECINE [MI]
RETRONECINE [HSDB]
DTXSID401020156
(1R,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizine-7-methanol
DTXCID601478002
(1r-trans)-2,3,5,7a-tetrahydro-1-hydroxy-1h-pyrrolizine-7-methanol
1H-pyrrolizine-7-methanol, 2,3,5,7a-tetrahydro-1-hydroxy-, (1R,7aR)
106-825-3
Retronecin
Senecifolinene
( )-Retronecine
UNII-2P5723M6II
1H-Pyrrolizine-7-methanol, 2,3,5,7a-beta-tetrahydro-1-alpha-hydroxy-
SCHEMBL673883
CHEBI:8821
Retronecine, analytical standard
HJSJELVDQOXCHO-HTQZYQBOSA-N
HY-N8419
MSK160717
STL564628
1H-Pyrrolizine-7-methanol, 2,3,5,7a-tetrahydro-1-hydroxy-, (1R-trans)-
AKOS003672869
FS-6720
DA-57405
1ST160717
CS-0144131
NS00121945
C06177
G13021
Q3933789
InChI=1/C8H13NO2/c10-5-6-1-3-9-4-2-7(11)8(6)9/h1,7-8,10-11H,2-5H2/t7-,8-/m1/s
- 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]
- 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]
CPRiL:
11471
SMILES: C1=CCN(C12)CCC2
Level: 0
Mol. Weight: 155.2 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.26
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.7
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.9
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.05
- Plasma Protein Binding
- 16.96
- 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
- 6.72
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.81
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 0.32
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 2.34
- Micronucleos
- Safe
- 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
- 0.05
- Rat (Acute)
- 2.24
- Rat (Chronic Oral)
- 1.65
- Fathead Minnow
- 2.73
- 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
- 309.26
- Hydration Free Energy
- -10.58
- Log(D) at pH=7.4
- -1.38
- Log(P)
- -1.0
- Log S
- 0.45
- Log(Vapor Pressure)
- -4.55
- Melting Point
- 119.42
- pKa Acid
- 10.59
- pKa Basic
- 9.11
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8294 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8294 |
| Iota toxin component Ia | Q46220 | Q46220_CLOPF | Clostridium perfringens | 3 | 0.8112 |
| Iota toxin component Ia | Q46220 | Q46220_CLOPF | Clostridium perfringens | 3 | 0.8112 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.7867 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.7867 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.7364 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.7364 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 3 | 0.7221 |
| Beta-galactosidase | P00722 | BGAL_ECOLI | Escherichia coli | 3 | 0.7221 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.7121 |
| Actin, alpha skeletal muscle | P68135 | ACTS_RABIT | Oryctolagus cuniculus | 3 | 0.7121 |