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Holarrhenine
- 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](O)[C@]24[C@H]3CC[C@@H]4[C@@H](N(C2)C)C)C1)C)C |
|---|---|
| InChI | InChI=1S/C24H40N2O/c1-15-19-8-9-20-18-7-6-16-12-17(25(3)4)10-11-23(16,2)21(18)13-22(27)24(19,20)14-26(15)5/h6,15,17-22,27H,7-14H2,1-5H3/t15-,17-,18-,19+,20-,21-,22+,23-,24+/m0/s1 |
| InChIKey | QESDNCVYXJTJRY-NFKVXLAQSA-N |
| Formula | C24H40N2O |
| HBA | 3 |
| HBD | 1 |
| MW | 372.6 |
| Rotatable Bonds | 1 |
| TPSA | 26.71 |
| LogP | 3.78 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.92 |
| Exact Mass | 372.31 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Holarrhena africana | Apocynaceae | Plantae | 2708850 |
Showing of synonyms
Holarrhenine
Holarrhenine [MI]
12beta-Hydroxyconessine
UNII-T3M9HB3VDU
T3M9HB3VDU
561-22-8
(3beta,12beta)-3-(Dimethylamino)CON-5-enin-12-ol
CON-5-Enin-12-ol, 3-(dimethylamino)-, (3beta,12beta)-
SCHEMBL4994484
12.BETA.-HYDROXYCONESSINE
Q27289623
(3.BETA.,12.BETA.)-3-(DIMETHYLAMINO)CON-5-ENIN-12-OL
CON-5-ENIN-12-OL, 3-(DIMETHYLAMINO)-, (3.BETA.,12.BETA.)-
- 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: 372.6 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.85
- 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
- -2.21
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.4
- Plasma Protein Binding
- 50.85
- 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
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 15.5
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.63
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.87
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 8.39
- 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
- -12.13
- Rat (Acute)
- 3.07
- Rat (Chronic Oral)
- 1.28
- Fathead Minnow
- 3.66
- 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
- 393.41
- Hydration Free Energy
- -7.45
- Log(D) at pH=7.4
- 2.25
- Log(P)
- 3.84
- Log S
- -3.25
- Log(Vapor Pressure)
- -7.58
- Melting Point
- 160.58
- pKa Acid
- 9.79
- pKa Basic
- 10.06