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3alpha-holaphyllamine
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Steroid Alkaloid
| Canonical Smiles | N[C@@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2C(=O)C)C)C1)C |
|---|---|
| InChI | InChI=1S/C21H33NO/c1-13(23)17-6-7-18-16-5-4-14-12-15(22)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19H,5-12,22H2,1-3H3/t15-,16+,17-,18+,19+,20+,21-/m1/s1 |
| InChIKey | GPRZXDPWGLHIQE-QYYVTAPASA-N |
| Formula | C21H33NO |
| HBA | 2 |
| HBD | 1 |
| MW | 315.5 |
| Rotatable Bonds | 1 |
| TPSA | 43.09 |
| LogP | 4.48 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.86 |
| Exact Mass | 315.26 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Holarrhena africana | Apocynaceae | Plantae | 2708850 |
Showing of synonyms
3alpha-holaphyllamine
Holamine
CHEMBL465586
SCHEMBL11056163
GPRZXDPWGLHIQE-QYYVTAPASA-N
DTXSID301307385
(3I+/-)-3-Aminopregn-5-en-20-one
28840-94-0
- 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: C1CCC(C12)CCC3C2CC=C4C3CCCC4
Level: 0
Mol. Weight: 315.5 g/mol
Antitrypanosomal
Absorption
- Caco-2 (logPapp)
- -4.82
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.330
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.59
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.230
- Plasma Protein Binding
- 60.7
- 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
- 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
- 20.620
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.300
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.140
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.180
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Toxic
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -1.670
- Rat (Acute)
- 2.350
- Rat (Chronic Oral)
- 1.360
- Fathead Minnow
- 3.920
- 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
- 376.750
- Hydration Free Energy
- -3.620
- Log(D) at pH=7.4
- 4.100
- Log(P)
- 4.02
- Log S
- -3.63
- Log(Vapor Pressure)
- -6.12
- Melting Point
- 162.94
- pKa Acid
- 11.42
- pKa Basic
- 8.38
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Steroid 17-alpha-hydroxylase/17,20 lyase | P05093 | CP17A_HUMAN | Homo sapiens | 3 | 0.9232 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9196 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8705 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.8667 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8427 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8398 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8114 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7772 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7693 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7480 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.7459 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.7208 |
| Mineralocorticoid receptor | P08235 | MCR_HUMAN | Homo sapiens | 3 | 0.7115 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7081 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7075 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.7043 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7001 |