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Diaboline
- Family: Plantae - Loganiaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | OC1OCC=C2C3C1C1N(C(=O)C)c4c(C51C(C3)N(C2)CC5)cccc4 |
|---|---|
| InChI | InChI=1S/C21H24N2O3/c1-12(24)23-16-5-3-2-4-15(16)21-7-8-22-11-13-6-9-26-20(25)18(19(21)23)14(13)10-17(21)22/h2-6,14,17-20,25H,7-11H2,1H3 |
| InChIKey | QSDMAJZSSDNJPO-UHFFFAOYSA-N |
| Formula | C21H24N2O3 |
| HBA | 4 |
| HBD | 1 |
| MW | 352.43 |
| Rotatable Bonds | 0 |
| TPSA | 53.01 |
| LogP | 1.66 |
| Number Rings | 6 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.57 |
| Exact Mass | 352.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Strychnos henningsii | Loganiaceae | Plantae | 1040887 |
Showing of synonyms
Diaboline
NSC277458
(17R)-1-Acetyl-19,20-didehydro-17,18-epoxycuran-17-ol
CHEMBL1969794
DTXSID70965137
NCI60_002258
Curan-17-ol,20-didehydro-17,18-epoxy-, (17R)-
1-(17-Hydroxy-19,20-didehydro-17,18-epoxycuran-1-yl)ethan-1-one
No compound-protein relationship available.
SMILES: c1cccc(c1C234)NC2C5C6C(CN(C3C6)CC4)=CCOC5
Level: 0
Mol. Weight: 352.43 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.76
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.83
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.47
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.67
- Plasma Protein Binding
- 19.58
- 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
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 9.43
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.02
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.82
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 7.05
- 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
- -9.87
- Rat (Acute)
- 3.73
- Rat (Chronic Oral)
- 1.78
- Fathead Minnow
- 4.37
- 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
- 426.23
- Hydration Free Energy
- -6.64
- Log(D) at pH=7.4
- 0.75
- Log(P)
- 0.95
- Log S
- -1.82
- Log(Vapor Pressure)
- -8.27
- Melting Point
- 186.41
- pKa Acid
- 8.42
- pKa Basic
- 6.19
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.8964 |
| 4,4'-diapophytoene synthase | A9JQL9 | CRTM_STAAU | Staphylococcus aureus | 3 | 0.8040 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.7827 |
| Diphtheria toxin | P00588 | DTX_CORBE | Corynephage beta | 3 | 0.7715 |
| Protein mono-ADP-ribosyltransferase PARP14 | Q460N5 | PAR14_HUMAN | Homo sapiens | 3 | 0.7656 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7641 |
| Acidic mammalian chitinase | Q9BZP6 | CHIA_HUMAN | Homo sapiens | 3 | 0.7636 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7493 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7453 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7426 |
| Cytochrome P450 monooxygenase PikC | O87605 | PIKC_STRVZ | Streptomyces venezuelae | 2 | 0.7312 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7205 |
| Heat shock 70 kDa protein 1A | P0DMV8 | HS71A_HUMAN | Homo sapiens | 3 | 0.7158 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7147 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7098 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7076 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7074 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7067 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7067 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7021 |
| Gag-Pol polyprotein | P03369 | POL_HV1A2 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7010 |