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Usaramine
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid
| Canonical Smiles | C/C=C/1\C[C@@H](C)[C@](O)(CO)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3 |
|---|---|
| InChI | InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3+/t11-,14-,15-,18-/m1/s1 |
| InChIKey | BCJMNZRQJAVDLD-FXGRWVCYSA-N |
| Formula | C18H25NO6 |
| HBA | 7 |
| HBD | 2 |
| MW | 351.4 |
| Rotatable Bonds | 1 |
| TPSA | 96.3 |
| LogP | 0.17 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.67 |
| Exact Mass | 351.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Senecio othonnae | Asteraceae | Plantae | 214901 |
| 2 | Senecio cineraria | Asteraceae | Plantae | 252537 |
| 3 | Senecio gnaphalodes | Asteraceae | Plantae | 2868836 |
| 4 | Senecio jacobaea | Asteraceae | Plantae | 98722 |
| 5 | Crotalaria agatiflora | Leguminosae/Fabaceae | Plantae | 1127378 |
| 6 | Crotalaria gillettii | Leguminosae/Fabaceae | Plantae | 1132206 |
Showing of synonyms
Usaramine
15503-87-4
Mucronatine
Usaramin
(15E)-Retrorsine
Trans-Retrorsine
(+)-Ursamine
Senecionan-11,16-dione, 12,18-dihydroxy-, (15E)-
(1R,4E,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
((7R,8R)-7-((Z)-2-methylbut-2-enoyl)oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl)methyl (2S)-2-hydroxy-2-((1S)-1-hydroxyethyl)-3-methyl-butanoate
(1R,4E,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo(9.5.1.014,17)heptadec-11-ene-3,8-dione
[(7R,8R)-7-[(Z)-2-methylbut-2-enoyl]oxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methyl-butanoate
Bcjmnzrqjavdld-rypqgoorsa-n
CHEBI:9912
[1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-(hydroxymethyl)-5-methyl-, (3E,5R,6S,14aR,14bR)-
(5R,6S,9a1R,14aR,E)-3-Ethylidene-6-hydroxy-6-(hydroxymethyl)-5-methyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
Usaramine (Standard)
CHEMBL520570
SCHEMBL19579599
CHEBI:92743
HY-N6931R
DTXSID001020178
HY-N6931
BDBM50480322
MSK170859
AKOS040757696
SMP1_000259
AC-33987
MS-25431
XU180151
1ST170859
CS-0027830
NS00094201
Q27108514
- Pelser PB, De Vos H, et al. (2005). Frequent gain and loss of pyrrolizidine alkaloids in the evolution of Senecio section Jacobaea (Asteraceae). Phytochemistry,2005,66,1285-1295. [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]
Pubchem:
5281756
Cas:
15503-87-4
Gnps:
CCMSLIB00006501541
Zinc:
ZINC000084811000
Kegg Ligand:
C10413
Chebi:
9912
Nmrshiftdb2:
60026240
Chembl:
CHEMBL520570
Bindingdb:
50480322
CPRiL:
49465
SMILES: C1OC(=O)CCCC(=C)C(=O)OC(C2C1=3)CCN2CC3
Level: 0
Mol. Weight: 351.4 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.93
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.94
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.16
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.59
- Plasma Protein Binding
- 25.18
- 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
- 4.04
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.21
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.03
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 9.86
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -5.5
- Rat (Acute)
- 3.87
- Rat (Chronic Oral)
- 2.25
- Fathead Minnow
- 4.01
- 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
- 400.15
- Hydration Free Energy
- -11.99
- Log(D) at pH=7.4
- 0.62
- Log(P)
- 0.22
- Log S
- -1.92
- Log(Vapor Pressure)
- -8.79
- Melting Point
- 185.82
- pKa Acid
- 6.13
- pKa Basic
- 6.51
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.9153 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.9153 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7651 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7651 |
| Multidrug transporter MdfA | P0AEY8 | MDFA_ECOLI | Escherichia coli | 3 | 0.7567 |
| Multidrug transporter MdfA | P0AEY8 | MDFA_ECOLI | Escherichia coli | 3 | 0.7567 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7426 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7426 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7300 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7300 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7297 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7297 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7181 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7181 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7128 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7128 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.7005 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.7005 |