Select a section from the left sidebar
Holarrhetine
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Steroid Alkaloid
| Canonical Smiles | CN1CC2C3(C1)C(OC(=O)CC=C(C)C)CC1C(C3CC2)CC=C2C1(C)CCC(C2)N(C)C |
|---|---|
| InChI | InChI=1S/C29H46N2O2/c1-19(2)7-12-27(32)33-26-16-25-23(24-11-9-21-17-31(6)18-29(21,24)26)10-8-20-15-22(30(4)5)13-14-28(20,25)3/h7-8,21-26H,9-18H2,1-6H3 |
| InChIKey | GZIHCSJHMIRZCP-UHFFFAOYSA-N |
| Formula | C29H46N2O2 |
| HBA | 4 |
| HBD | 0 |
| MW | 454.7 |
| Rotatable Bonds | 4 |
| TPSA | 32.78 |
| LogP | 5.3 |
| 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 | Funtumia elastica | Apocynaceae | Plantae | 69379 |
| 2 | Holarrhena africana | Apocynaceae | Plantae | 2708850 |
Showing of synonyms
Holarrhetine
- Ma'mag LK, Zintchem AAA, et al. (2021). Antiplasmodial and antileishmanial inhibitory activity of triterpenes and steroidal alkaloid from the leaves of Funtumia elastica (Preuss) Stapf (Apocynaceae).. Fitoterapia,2021, 151, 104869. [View] [PubMed]
- 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]
Pubchem:
5318071
No compound-protein relationship available.
SMILES: C1NCC(C123)CCC2C4C(CC3)C5C(=CC4)CCCC5
Level: 0
Mol. Weight: 454.7 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.01
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.89
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -2.26
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.64
- Plasma Protein Binding
- 22.56
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.07
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.62
- 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
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 9.44
- 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
- -165.04
- Rat (Acute)
- 3.03
- Rat (Chronic Oral)
- 1.37
- Fathead Minnow
- 4.82
- 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
- 435.99
- Hydration Free Energy
- -3.08
- Log(D) at pH=7.4
- 3.66
- Log(P)
- 5.85
- Log S
- -4.68
- Log(Vapor Pressure)
- -7.21
- Melting Point
- 141.33
- pKa Acid
- 8.13
- pKa Basic
- 9.09
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8330 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7974 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 3 | 0.7956 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7795 |
| 17-beta-hydroxysteroid dehydrogenase type 1 | P14061 | DHB1_HUMAN | Homo sapiens | 3 | 0.7785 |
| Multidrug transporter MdfA | P0AEY8 | MDFA_ECOLI | Escherichia coli | 3 | 0.7771 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7487 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7319 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7277 |
| Retinol dehydratase | Q26490 | Q26490_SPOFR | Spodoptera frugiperda | 3 | 0.7272 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 2 | 0.7198 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.7156 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7126 |
| Steroid 17-alpha-hydroxylase/17,20 lyase | P05093 | CP17A_HUMAN | Homo sapiens | 3 | 0.7066 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7064 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7027 |