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Pseudostrychnine
- Family: Plantae - Loganiaceae
- Kingdom: Plantae
- Class: Alkaloid
| Canonical Smiles | O=C1C[C@@H]2OCC=C3[C@H]4[C@@H]2[C@@H]2N1c1ccccc1[C@]12CCN([C@]1(C4)O)C3 |
|---|---|
| InChI | InChI=1S/C21H22N2O3/c24-17-9-16-18-13-10-21(25)20(6-7-22(21)11-12(13)5-8-26-16)14-3-1-2-4-15(14)23(17)19(18)20/h1-5,13,16,18-19,25H,6-11H2/t13-,16-,18-,19-,20-,21+/m0/s1 |
| InChIKey | HCCFPODVEOBUMM-YOQTYQRRSA-N |
| Formula | C21H22N2O3 |
| HBA | 4 |
| HBD | 1 |
| MW | 350.42 |
| Rotatable Bonds | 0 |
| TPSA | 53.01 |
| LogP | 1.41 |
| Number Rings | 7 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.57 |
| Exact Mass | 350.16 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Strychnos icaja | Loganiaceae | Plantae | 1040889 |
Showing of synonyms
Pseudostrychnine
16-hydroxystrychnine
(-)-pseudostrychnine
CHEBI:132666
(4aR,5aR,8aS,13aS,15aS,15bR)-5a-hydroxy-2,4a,5,7,8,13a,15,15a,15b,16-decahydro4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinolin-14-one
465-62-3
(4aR,5aR,8aS,13aS,15aS,15bR)-5a-hydroxy-2,4a,5,7,8,13a,15,15a,15b,16-decahydro4,6-methanoindolo(3,2,1-ij)oxepino(2,3,4-de)pyrrolo(2,3-h)quinolin-14-one
(4aR,5aR,8aS,13aS,15aS,15bR)-5a-hydroxy-2,4a,5,7,8,13a,15,15a,15b,16-decahydro4,6-methanoindolo(3,2,1-ij)oxepino(2,3,4-de)pyrrolo(2,3-h)quinoline-14-one
(4aR,5aR,8aS,13aS,15aS,15bR)-5a-hydroxy-2,4a,5,7,8,13a,15,15a,15b,16-decahydro4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-14-one
Strychnidin-10-one, 16-hydroxy-(9CI)
16-hydroxy-strychnine
Nsc 99792
Psi-strychnine
Strychnidin-10-one, 16-hydroxy-
16-Hydroxystrychnidin-10-one
CHEMBL2164943
Pubchem:
21723446
Cas:
465-62-3
Gnps:
CCMSLIB00004680041
Zinc:
ZINC000001657257
Chebi:
132666
Nmrshiftdb2:
60073088
Metabolights:
MTBLC132666
Chembl:
CHEMBL2164943
No compound-protein relationship available.
SMILES: c1cccc(c1C234)N5C2C6C7C(CN(C3C7)CC4)=CCOC6CC5=O
Level: 0
Mol. Weight: 350.42 g/mol
Anti-plasmodial
Absorption
- Caco-2 (logPapp)
- -4.94
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.9
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.74
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.83
- Plasma Protein Binding
- 52.15
- 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
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.55
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.84
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.28
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.82
- 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
- -14.59
- Rat (Acute)
- 4.85
- Rat (Chronic Oral)
- 2.04
- Fathead Minnow
- 3.97
- 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
- 459.45
- Hydration Free Energy
- -5.41
- Log(D) at pH=7.4
- 0.8
- Log(P)
- 1.57
- Log S
- -2.92
- Log(Vapor Pressure)
- -9.7
- Melting Point
- 298.52
- pKa Acid
- 8.17
- pKa Basic
- 6.69
| 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 | 0.9422 |
| cGMP-dependent protein kinase 2 | Q13237 | KGP2_HUMAN | Homo sapiens | 3 | 0.8716 |
| cAMP-dependent protein kinase type I-alpha regulatory subunit | P00514 | KAP0_BOVIN | Bos taurus | 3 | 0.8459 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8169 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7965 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7823 |
| cAMP-dependent protein kinase type II-beta regulatory subunit | P12369 | KAP3_RAT | Rattus norvegicus | 3 | 0.7822 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7542 |
| cGMP-dependent protein kinase 1 | Q13976 | KGP1_HUMAN | Homo sapiens | 3 | 0.7451 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7379 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7084 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7079 |