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Hydroxystrychnine
- Family: Plantae - Loganiaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Monoindole Alkaloid
| Canonical Smiles | OC1=C2CN3CCC45[C@@H]3C[C@@H]2[C@H]2[C@@H](OC1)CC(=O)N([C@H]42)c1c5cccc1 |
|---|---|
| InChI | InChI=1S/C21H22N2O3/c24-15-10-26-16-8-18(25)23-14-4-2-1-3-13(14)21-5-6-22-9-12(15)11(7-17(21)22)19(16)20(21)23/h1-4,11,16-17,19-20,24H,5-10H2/t11-,16-,17-,19-,20-,21?/m0/s1 |
| InChIKey | DHNSIKSFKOEIIE-ILZATJAISA-N |
| Formula | C21H22N2O3 |
| HBA | 4 |
| HBD | 1 |
| MW | 350.42 |
| Rotatable Bonds | 0 |
| TPSA | 53.01 |
| LogP | 1.98 |
| 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
Hydroxystrychnine
22-Hydroxystrychnine
134250-41-2
Strychnidin-10-one, 22-hydroxy-
(4aR,5aS,13aS,15aS,15bR)-3-hydroxy-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinolin-14-one
22-hydroxystrychnidin-10-one
DTXSID70928545
- Tchinda A, Tamze V, et al. (2012). Alkaloids from the stem bark of Strychnos icaja. Phytochemistry Letters, 2012, 5(1), 108-113. [View]
Pubchem:
196866
Cas:
134250-41-2
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)
- -4.75
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.750
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.51
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.580
- Plasma Protein Binding
- 47.4
- 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
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 8.640
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.400
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.270
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.140
- 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
- -16.560
- Rat (Acute)
- 4.300
- Rat (Chronic Oral)
- 1.950
- Fathead Minnow
- 4.020
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 435.410
- Hydration Free Energy
- -5.180
- Log(D) at pH=7.4
- 0.670
- Log(P)
- 0.74
- Log S
- -2.6
- Log(Vapor Pressure)
- -9.26
- Melting Point
- 279.54
- pKa Acid
- 6.96
- pKa Basic
- 7.0
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Acidic mammalian chitinase | Q9BZP6 | CHIA_HUMAN | Homo sapiens | 3 | 0.8043 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P28845 | DHI1_HUMAN | Homo sapiens | 3 | 0.7879 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7518 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7463 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7411 |
| Pantothenate kinase | P9WPA7 | COAA_MYCTU | Mycobacterium tuberculosis | 3 | 0.7404 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7338 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7232 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7196 |
| Adenosine 5'-monophosphoramidase HINT1 | P80912 | HINT1_RABIT | Oryctolagus cuniculus | 2 | 0.7196 |
| Prenyltransferase | Q4R2T2 | Q4R2T2_STRC1 | Streptomyces sp | 2 | 0.7181 |
| Diamine acetyltransferase 1 | P21673 | SAT1_HUMAN | Homo sapiens | 2 | 0.7153 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 2 | 0.7147 |
| Prostaglandin F2a synthase | Q8I6L9 | Q8I6L9_TRYCR | Trypanosoma cruzi | 2 | 0.7113 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7102 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7080 |
| NADPH dehydrogenase 1 | Q02899 | OYE1_SACPS | Saccharomyces pastorianus | 2 | 0.7041 |