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Holadienine
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Steroid Alkaloid
| Canonical Smiles | O=C1C=C[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]23[C@H]1CC[C@@H]3[C@@H](N(C2)C)C)C |
|---|---|
| InChI | InChI=1S/C22H31NO/c1-14-18-6-7-20-17-5-4-15-12-16(24)8-10-21(15,2)19(17)9-11-22(18,20)13-23(14)3/h8,10,12,14,17-20H,4-7,9,11,13H2,1-3H3/t14-,17+,18+,19-,20-,21-,22-/m0/s1 |
| InChIKey | PSOQPSXOOXHHBU-LJZXKFISSA-N |
| Formula | C22H31NO |
| HBA | 2 |
| HBD | 0 |
| MW | 325.5 |
| Rotatable Bonds | 0 |
| TPSA | 20.31 |
| LogP | 4.22 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.77 |
| Exact Mass | 325.24 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Holarrhena africana | Apocynaceae | Plantae | 2708850 |
Showing of synonyms
Holadienine
- 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)=CC(=O)C=C5
Level: 0
Mol. Weight: 325.5 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.87
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.640
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.84
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.180
- Plasma Protein Binding
- 60.55
- 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
- 13.110
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.820
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.930
- Liver Injury II
- Safe
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.800
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Toxic
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -4.790
- Rat (Acute)
- 2.970
- Rat (Chronic Oral)
- 1.330
- Fathead Minnow
- 3.790
- 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
- 427.750
- Hydration Free Energy
- -6.100
- Log(D) at pH=7.4
- 2.930
- Log(P)
- 3.71
- Log S
- -3.89
- Log(Vapor Pressure)
- -5.78
- Melting Point
- 157.26
- pKa Acid
- 8.69
- pKa Basic
- 8.72
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 3 | 0.9384 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.9294 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9232 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.9026 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8968 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8935 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8913 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8846 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.8826 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 3 | 0.8784 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8765 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.8732 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 4 | 0.7833 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7813 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7710 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7649 |
| 4,4'-diapophytoene synthase | A9JQL9 | CRTM_STAAU | Staphylococcus aureus | 3 | 0.7560 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7499 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7467 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7426 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7425 |
| Glucocorticoid receptor | P04150 | GCR_HUMAN | Homo sapiens | 3 | 0.7414 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7377 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7365 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7340 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7338 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7300 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7297 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 3 | 0.7232 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7196 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7190 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7187 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7184 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7163 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7155 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7139 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7134 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7131 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7125 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7124 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7117 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7114 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7108 |
| NPC intracellular cholesterol transporter 1 | O15118 | NPC1_HUMAN | Homo sapiens | 3 | 0.7097 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7093 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7088 |
| Androgen receptor | O97775 | ANDR_PANTR | Pan troglodytes | 4 | 0.7079 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7072 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7062 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7054 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 2 | 0.7040 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7039 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7021 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 4 | 0.7009 |
| Nuclear receptor coactivator 2 | Q15596 | NCOA2_HUMAN | Homo sapiens | 3 | 0.7008 |