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3alpha-dihydroholaphyllamine
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Steroid Alkaloid
| Canonical Smiles | N[C@@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2C(=O)C)C)C |
|---|---|
| InChI | InChI=1S/C21H35NO/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/h14-19H,4-12,22H2,1-3H3/t14-,15+,16-,17+,18-,19-,20-,21+/m0/s1 |
| InChIKey | POWBIOMTXFDIOP-SYBPFIFISA-N |
| Formula | C21H35NO |
| HBA | 2 |
| HBD | 1 |
| MW | 317.52 |
| Rotatable Bonds | 1 |
| TPSA | 43.09 |
| LogP | 4.56 |
| Number Rings | 4 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.95 |
| Exact Mass | 317.27 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Holarrhena africana | Apocynaceae | Plantae | 2708850 |
Showing of synonyms
3alpha-dihydroholaphyllamine
Funtumine
474-45-3
EINECS 207-483-9
3-alpha-Amino-5-alpha-pregnan-20-one
3-alpha-Amino-20-oxo-5-alpha-pregnane
UNII-29N9T471HT
FUNTUMIN
29N9T471HT
FUNTUMINE [MI]
1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-amino-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
FUNTUMINE, (+)-
5-alpha-Pregnan-20-one, 3-alpha-amino-
DTXSID90878598
Pregnan-20-one, 3-amino-, (3-alpha,5-alpha)-
(3.ALPHA.,5.ALPHA.)-3-AMINOPREGNAN-20-ONE
PREGNAN-20-ONE, 3-AMINO-, (3.ALPHA.,5.ALPHA.)-
1-((3R,5S,8R,9S,10S,13S,14S,17S)-3-amino-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-17-yl)ethanone
DTXCID601016642
(3ALPHA,5ALPHA)-3-AMINOPREGNAN-20-ONE
Pregnan-20-one, 3-amino-, (3-alpha,5-alpha)-(9CI)
PREGNAN-20-ONE, 3-AMINO-, (3ALPHA,5ALPHA)-
207-483-9
Powbiomtxfdiop-uhfffaoysa-n
3alpha-Amino-5alpha-pregnan-20-one
Funtumine base
3a-amino-5a-pregnan-20-one
CHEBI:5193
SCHEMBL4998838
CHEMBL2322569
AKOS015994774
MD-0229
NS00042883
Q27106686
- 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:
101702
Cas:
474-45-3
Zinc:
ZINC000004098874
Kegg Ligand:
C10806
Chebi:
5193
Chembl:
CHEMBL2322569
Comptox:
DTXSID90878598
No compound-protein relationship available.
SMILES: C1CCC(C12)CCC3C2CCC4C3CCCC4
Level: 0
Mol. Weight: 317.52 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.79
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.290
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.76
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 1.210
- Plasma Protein Binding
- 66.23
- 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
- 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
- 20.150
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.030
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.400
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.450
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Toxic
- NR-AR-LBD
- Toxic
- NR-Aromatase
- Safe
- NR-ER
- Toxic
- NR-ER-LBD
- Toxic
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -2.230
- Rat (Acute)
- 2.430
- Rat (Chronic Oral)
- 1.370
- 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
- 377.360
- Hydration Free Energy
- -2.730
- Log(D) at pH=7.4
- 4.710
- Log(P)
- 4.18
- Log S
- -3.85
- Log(Vapor Pressure)
- -6.37
- Melting Point
- 165.25
- pKa Acid
- 11.47
- pKa Basic
- 8.77
| 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 | 0.9351 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9272 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.9095 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.9054 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9012 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.8162 |
| Sex hormone-binding globulin | P04278 | SHBG_HUMAN | Homo sapiens | 3 | 0.8086 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.8060 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.7863 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7858 |
| Sulfotransferase 2B1 | O00204 | ST2B1_HUMAN | Homo sapiens | 3 | 0.7752 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7655 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 3 | 0.7397 |
| Cytochrome P450 monooxygenase | Q5YNS8 | Q5YNS8_NOCFA | Nocardia farcinica | 3 | 0.7254 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7244 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7127 |
| ADP-ribosylation factor 1 | P84080 | ARF1_BOVIN | Bos taurus | 3 | 0.7020 |