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Tetraphyllicine
- Family: Plantae - Apocynaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Indole Alkaloid
| Canonical Smiles | C/C=C\1/CN2[C@@H]3[C@@H]4[C@H]1C[C@H]2[C@H]1[C@@]([C@@H]4O)(C3)c2c(N1C)cccc2 |
|---|---|
| InChI | InChI=1S/C20H24N2O/c1-3-11-10-22-15-8-12(11)17-16(22)9-20(19(17)23)13-6-4-5-7-14(13)21(2)18(15)20/h3-7,12,15-19,23H,8-10H2,1-2H3/b11-3-/t12-,15-,16-,17-,18-,19+,20+/m0/s1 |
| InChIKey | VBEQZFNVRMPLSM-MVVFEDHTSA-N |
| Formula | C20H24N2O |
| HBA | 3 |
| HBD | 1 |
| MW | 308.42 |
| Rotatable Bonds | 0 |
| TPSA | 26.71 |
| LogP | 2.16 |
| Number Rings | 7 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 23 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.6 |
| Exact Mass | 308.19 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Rauvolfia caffra | Apocynaceae | Plantae | 947877 |
Showing of synonyms
Tetraphyllicine
NSC 72114
DTXSID501319071
509-38-6
NSC72114
DTXCID201746796
808-275-6
Ajmalan-17-ol, 19,20-didehydro-, (17R,19E)-
No compound-protein relationship available.
SMILES: C=C(C1)C(C2)C(C3)C(C4)N1C2C5Nc(c6C345)cccc6
Level: 0
Mol. Weight: 308.42 g/mol
Antimicrobial
Cytotoxic
Absorption
- Caco-2 (logPapp)
- -4.6
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.01
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- -1.73
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.5
- Plasma Protein Binding
- 57.78
- 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
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 10.93
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Toxic
- Bee
- Toxic
- Bioconcentration Factor
- -0.05
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.2
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 5.9
- Micronucleos
- Toxic
- 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
- -0.9
- Rat (Acute)
- 3.95
- Rat (Chronic Oral)
- 1.61
- Fathead Minnow
- 3.96
- 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
- 417.59
- Hydration Free Energy
- -4.37
- Log(D) at pH=7.4
- 1.39
- Log(P)
- 1.84
- Log S
- -3.27
- Log(Vapor Pressure)
- -9.24
- Melting Point
- 219.85
- pKa Acid
- 8.13
- pKa Basic
- 8.22
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8231 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.7966 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7830 |
| Prolyl endopeptidase | P23687 | PPCE_PIG | Sus scrofa | 3 | 0.7789 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7666 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 2 | 0.7619 |
| Prolyl endopeptidase | P23687 | PPCE_PIG | Sus scrofa | 3 | 0.7519 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 2 | 0.7330 |
| Histidinol dehydrogenase | P06988 | HISX_ECOLI | Escherichia coli | 2 | 0.7327 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 2 | 0.7307 |
| rRNA methylase | Q8DSS3 | Q8DSS3_STRMU | Streptococcus mutans serotype c | 2 | 0.7299 |
| Glutamate receptor 2 | P19491 | GRIA2_RAT | Rattus norvegicus | 2 | 0.7281 |
| Beta-1 adrenergic receptor | P07700 | ADRB1_MELGA | Meleagris gallopavo | 2 | 0.7278 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | O02604 | DRTS_PLAVI | Plasmodium vivax | 3 | 0.7246 |
| Prolyl endopeptidase | P23687 | PPCE_PIG | Sus scrofa | 3 | 0.7235 |
| Formylmethanofuran--tetrahydromethanopterin formyltransferase | Q49610 | FTR_METKA | Methanopyrus kandleri | 3 | 0.7163 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7082 |
| Diphtheria toxin | P00588 | DTX_CORBE | Corynephage beta | 2 | 0.7066 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 2 | 0.7064 |
| Acidic mammalian chitinase | Q9BZP6 | CHIA_HUMAN | Homo sapiens | 2 | 0.7003 |