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Trichodesmine
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
- Class: Alkaloid
| Canonical Smiles | CC([C@H]1C(=O)O[C@@H]2CCN3[C@@H]2C(=CC3)COC(=O)[C@]([C@]1(C)O)(C)O)C |
|---|---|
| InChI | InChI=1S/C18H27NO6/c1-10(2)13-15(20)25-12-6-8-19-7-5-11(14(12)19)9-24-16(21)18(4,23)17(13,3)22/h5,10,12-14,22-23H,6-9H2,1-4H3/t12-,13+,14-,17-,18+/m1/s1 |
| InChIKey | SOODLZHDDSGRKL-FOOXYVKASA-N |
| Formula | C18H27NO6 |
| HBA | 7 |
| HBD | 2 |
| MW | 353.42 |
| Rotatable Bonds | 1 |
| TPSA | 96.3 |
| LogP | 0.24 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 25 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.78 |
| Exact Mass | 353.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Trichodesma africanum | Boraginaceae | Plantae | 379304 |
| 2 | Crotalaria mildbraedii | Leguminosae/Fabaceae | Plantae | 1977593 |
Showing of synonyms
Trichodesmine
548-90-3
(1R,4R,5R,6R,16R)-5,6-dihydroxy-5,6-dimethyl-4-propan-2-yl-2,8-dioxa-13-azatricyclo[8.5.1.013,16]hexadec-10-ene-3,7-dione
(13alpha,14alpha)-14,19-Dihydro-12,13-dihydroxy-19-methylcrotalanan-11,15-dione
(1R,4R,5R,6R,16R)-5,6-dihydroxy-5,6-dimethyl-4-propan-2-yl-2,8-dioxa-13-azatricyclo(8.5.1.013,16)hexadec-10-ene-3,7-dione
2H-(1,6)Dioxacycloundecino(2,3,4-gh)pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-decahydro-4,5-dihydroxy-4,5-dimethyl-3-(1-methylethyl)-, (3R,4R,5R,13aR,13bR)-
2H-[1,6]Dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione, 4,5,8,10,12,13,13a,13b-decahydro-4,5-dihydroxy-4,5-dimethyl-3-(1-methylethyl)-, (3R,4R,5R,13aR,13bR)-
(13 alpha,14 alpha)-14,19-dihydro-12,13-dihydroxy-19-methylcrotalanan-11,15-dione
Soodlzhddsgrkl-osarjhgosa-n
(3R,4R,5R,13aR,13bR)-4,5-dihydroxy-4,5-dimethyl-3-(propan-2-yl)-4,5,8,10,12,13,13a,13b-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
(3R,4R,5R,8a1R,13aR)-4,5-dihydroxy-3-isopropyl-4,5-dimethyl-4,5,8,8a1,10,12,13,13a-octahydro-2H-[1,6]dioxacycloundecino[2,3,4-gh]pyrrolizine-2,6(3H)-dione
MLS001164088
CHEMBL1573073
C18H27NO6
DTXSID50970148
HMS2868L15
MSK14182
BBL033962
STK801818
AKOS005622721
CCG-208373
1ST14182
DA-78607
FT161629
HY-12535
SMR000539438
VS-12350
CS-0011992
NS00125373
SR-01000801015
SR-01000801015-3
(1R,4R,5R,6R,16R)-5,6-DIHYDROXY-4-ISOPROPYL-5,6-DIMETHYL-2,8-DIOXA-13-AZATRICYCLO[8.5.1.0(1)(3),(1)?]HEXADEC-10-ENE-3,7-DIONE
(1R,4R,5R,6R,16R)-5,6-DIHYDROXY-5,6-DIMETHYL-4-(PROPAN-2-YL)-2,8-DIOXA-13-AZATRICYCLO[8.5.1.0(1)(3),(1)?]HEXADEC-10-ENE-3,7-DIONE
- Omar M, Defeo J, et al. (1983). Chemical and toxicity studies of Trichodesma africanum L.. Journal of Natural Products,1983,46(2),153-156. [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)CCCC(=O)OC3
Level: 0
Mol. Weight: 353.42 g/mol
Toxin
Absorption
- Caco-2 (logPapp)
- -4.8
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.89
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.26
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.49
- Plasma Protein Binding
- 29.4
- 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
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.08
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.56
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.73
- 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
- -2.96
- Rat (Acute)
- 3.69
- Rat (Chronic Oral)
- 1.88
- Fathead Minnow
- 3.72
- 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
- 384.86
- Hydration Free Energy
- -9.53
- Log(D) at pH=7.4
- 0.93
- Log(P)
- 0.42
- Log S
- -1.92
- Log(Vapor Pressure)
- -7.8
- Melting Point
- 201.04
- pKa Acid
- 6.2
- pKa Basic
- 6.74
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8447 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8447 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 4 | 0.8170 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 4 | 0.8170 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7892 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7892 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7210 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7210 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.7038 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.7038 |