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Holarrhesine
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Steroid Alkaloid
| Canonical Smiles | CN[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2C[C@@H](OC(=O)CC=C(C)C)[C@]24[C@H]3CC[C@@H]4[C@@H](N(C2)C)C)C1)C |
|---|---|
| InChI | InChI=1S/C29H46N2O2/c1-18(2)7-12-27(32)33-26-16-25-22(9-8-20-15-21(30-5)13-14-28(20,25)4)24-11-10-23-19(3)31(6)17-29(23,24)26/h7-8,19,21-26,30H,9-17H2,1-6H3/t19-,21-,22-,23+,24-,25-,26+,28-,29+/m0/s1 |
| InChIKey | BJEAHAPLWWPUQZ-XGHHNQJOSA-N |
| Formula | C29H46N2O2 |
| HBA | 4 |
| HBD | 1 |
| MW | 454.7 |
| Rotatable Bonds | 4 |
| TPSA | 41.57 |
| LogP | 5.35 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.83 |
| Exact Mass | 454.36 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Holarrhena africana | Apocynaceae | Plantae | 2708850 |
Showing of synonyms
Holarrhesine
CHEMBL195752
- Nnadi CO, Nwodo NJ, et al. (2017). Steroid alkaloids from Holarrhena africana with strong activity against Trypanosoma brucei rhodesiense. Molecules, 2017, 22(7), 1129. [View]
No compound-protein relationship available.
SMILES: C1NCC(C123)CCC2C4C(CC3)C5C(=CC4)CCCC5
Level: 0
Mol. Weight: 454.7 g/mol
Antitrypanosomal
Absorption
- Caco-2 (logPapp)
- -5.03
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.85
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.45
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.92
- Plasma Protein Binding
- 66.45
- 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
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.26
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.12
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.99
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 7.53
- Micronucleos
- Safe
- 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
- -182.28
- Rat (Acute)
- 2.93
- Rat (Chronic Oral)
- 1.38
- Fathead Minnow
- 3.92
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 459.17
- Hydration Free Energy
- -3.0
- Log(D) at pH=7.4
- 4.02
- Log(P)
- 5.51
- Log S
- -4.91
- Log(Vapor Pressure)
- -7.72
- Melting Point
- 188.66
- pKa Acid
- 9.24
- pKa Basic
- 8.58
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.8015 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7706 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7344 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7165 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7139 |