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Niloticin
- Family: Plantae - Rutaceae
- Kingdom: Plantae
-
Class: Terpenoid
- Subclass: Triterpenoid
| Canonical Smiles | C[C@H]([C@@H]1CC[C@]2([C@@]1(C)CC[C@H]1C2=CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C[C@H]([C@@H]1OC1(C)C)O |
|---|---|
| InChI | InChI=1S/C30H48O3/c1-18(17-22(31)25-27(4,5)33-25)19-11-15-30(8)21-9-10-23-26(2,3)24(32)13-14-28(23,6)20(21)12-16-29(19,30)7/h9,18-20,22-23,25,31H,10-17H2,1-8H3/t18-,19-,20-,22+,23-,25-,28+,29-,30+/m0/s1 |
| InChIKey | GKQMMZUXYRXFOH-QBLSGNHRSA-N |
| Formula | C30H48O3 |
| HBA | 3 |
| HBD | 1 |
| MW | 456.71 |
| Rotatable Bonds | 4 |
| TPSA | 49.83 |
| LogP | 6.73 |
| Number Rings | 5 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 33 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.9 |
| Exact Mass | 456.36 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Turraea nilotica | Meliaceae | Plantae | 992803 |
| 2 | Vepris uguenensis | Rutaceae | Plantae | 2695421 |
| 3 | Vepris uguenensis | Rutaceae | Plantae | 2695421 |
Showing of synonyms
Niloticin
115404-57-4
(5R,9R,10R,13S,14S,17S)-17-[(2S,4R)-4-[(2S)-3,3-dimethyloxiran-2-yl]-4-hydroxybutan-2-yl]-4,4,10,13,14-pentamethyl-1,2,5,6,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Lanost-7-en-3-one, 24,25-epoxy-23-hydroxy-, (13alpha,14beta,17alpha,20S,23R,24S)-
HY-N3188
AKOS040744637
CID 14021529
DA-66099
FS-10176
CS-0023535
(13,14,17,20S,23R,24S)-24,25-Epoxy-23-hydroxylanost-7-en-3-one
Lanost-7-en-3-one, 24,25-epoxy-23-hydroxy-, (13|A,14|A,17|A,20S,23R,24S)-
- Irungu BN, Adipo N, et al. (2015). Antiplasmodial and cytotoxic activities of the constituents of Turraea robusta and Turraea nilotica.. Journal of Ethnopharmacology,2015,174,419-425. [View] [PubMed]
- Kiplimo JJ, Shahidul Islam M, et al. (2012). Ring A-seco limonoids and flavonoids from the Kenyan Vepris uguenensis Engl. and their antioxidant activity. Phytochemistry,2012,83(2012),136-143. [View] [PubMed]
- Kiplimo JJ, Koorbanally NA. (2012). The phytochemistry and biological activity of secondary metabolites from Kenyan Vernonia and Vepris species. PhD Thesis, University of Kwazulu-Natal, South Africa,2012. [View] [PubMed]
CPRiL:
452379
SMILES: O1CC1CCCC(CC2)C(C23)CCC4C3=CCC5C4CCC(=O)C5
Level: 1
Mol. Weight: 456.71 g/mol
SMILES: C1CCC(C12)CCC3C2=CCC4C3CCC(=O)C4
Level: 0
Mol. Weight: 456.71 g/mol
SMILES: C1CO1
Level: 0
Mol. Weight: 456.71 g/mol
Anti-plasmodial
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -5.05
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.62
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.44
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.8
- Plasma Protein Binding
- 71.54
- 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
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 14.57
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 0.87
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.05
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 7.15
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Toxic
- T. Pyriformis
- -109.95
- Rat (Acute)
- 2.01
- Rat (Chronic Oral)
- 1.57
- Fathead Minnow
- 4.0
- 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
- 450.2
- Hydration Free Energy
- -2.59
- Log(D) at pH=7.4
- 5.96
- Log(P)
- 6.39
- Log S
- -6.56
- Log(Vapor Pressure)
- -7.67
- Melting Point
- 162.03
- pKa Acid
- 8.35
- pKa Basic
- 5.97
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9126 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.9126 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9122 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.9122 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8795 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.8795 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 4 | 0.8604 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 4 | 0.8604 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8147 |
| Retinol-binding protein 1 | P02696 | RET1_RAT | Rattus norvegicus | 3 | 0.8147 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8119 |
| Soluble acetylcholine receptor | Q8WSF8 | Q8WSF8_APLCA | Aplysia californica | 3 | 0.8119 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 3 | 0.8095 |
| Aldo-keto reductase family 1 member C1 | Q04828 | AK1C1_HUMAN | Homo sapiens | 3 | 0.8095 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7941 |
| Retinoic acid receptor RXR-alpha | P19793 | RXRA_HUMAN | Homo sapiens | 3 | 0.7941 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7810 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7810 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7772 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 3 | 0.7772 |
| Oxysterols receptor LXR-beta | P55055 | NR1H2_HUMAN | Homo sapiens | 4 | 0.7741 |
| Oxysterols receptor LXR-beta | P55055 | NR1H2_HUMAN | Homo sapiens | 4 | 0.7741 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7737 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7737 |
| Mycinamicin VI 2''-O-methyltransferase | Q83WF2 | MYCE_MICGR | Micromonospora griseorubida | 4 | 0.7728 |
| Mycinamicin VI 2''-O-methyltransferase | Q83WF2 | MYCE_MICGR | Micromonospora griseorubida | 4 | 0.7728 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7700 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7700 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7682 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 3 | 0.7682 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7568 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7568 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7549 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7549 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7465 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 3 | 0.7465 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7381 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7381 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 2 | 0.7380 |
| Reaction center protein L chain | P0C0Y7 | RCEH_RHOSH | Rhodobacter sphaeroides | 2 | 0.7380 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.7225 |
| Nuclear receptor subfamily 1 group I member 3 | O35627 | NR1I3_MOUSE | Mus musculus | 3 | 0.7225 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7223 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7223 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 4 | 0.7202 |
| Protein BRASSINOSTEROID INSENSITIVE 1 | O22476 | BRI1_ARATH | Arabidopsis thaliana | 4 | 0.7202 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7141 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 2 | 0.7141 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7116 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7116 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7114 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7114 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7046 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7046 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 3 | 0.7046 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7046 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7027 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7027 |