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Zizyphine F
- Family: Plantae - Rhamnaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Cyclopeptide Alkaloid
| Canonical Smiles | CC[C@@H]([C@@H](C(=O)N1CC[C@H]2[C@H]1C(=O)N1CCC[C@H]1C(=O)N/C=C\c1ccc(O2)cc1O)NC(=O)[C@H]([C@H](CC)C)N(C)C)C |
|---|---|
| InChI | InChI=1S/C32H47N5O6/c1-7-19(3)26(34-30(40)27(35(5)6)20(4)8-2)31(41)37-17-14-25-28(37)32(42)36-16-9-10-23(36)29(39)33-15-13-21-11-12-22(43-25)18-24(21)38/h11-13,15,18-20,23,25-28,38H,7-10,14,16-17H2,1-6H3,(H,33,39)(H,34,40)/b15-13-/t19-,20-,23-,25-,26-,27-,28-/m0/s1 |
| InChIKey | BRUITOXHBSVJME-IIMYRAIISA-N |
| Formula | C32H47N5O6 |
| HBA | 7 |
| HBD | 3 |
| MW | 597.76 |
| Rotatable Bonds | 8 |
| TPSA | 131.52 |
| LogP | 2.34 |
| Number Rings | 5 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 43 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.62 |
| Exact Mass | 597.35 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ziziphus spina-christi | Rhamnaceae | Plantae | 264981 |
Showing of synonyms
Zizyphine F
55839-64-0
DTXSID40474625
(2S,3S)-2-(dimethylamino)-N-[(2S,3S)-1-[(3S,7S,13S,16Z)-19-hydroxy-8,14-dioxo-2-oxa-6,9,15-triazatetracyclo[16.2.2.03,7.09,13]docosa-1(20),16,18,21-tetraen-6-yl]-3-methyl-1-oxopentan-2-yl]-3-methylpentanamide
(2S,3S)-2-(dimethylamino)-N-((2S,3S)-1-((3S,7S,13S,16Z)-19-hydroxy-8,14-dioxo-2-oxa-6,9,15-triazatetracyclo(16.2.2.03,7.09,13)docosa-1(20),16,18,21-tetraen-6-yl)-3-methyl-1-oxopentan-2-yl)-3-methylpentanamide
DTXCID80425439
C10016
CHEBI:10122
Q27108593
- Abdel-galil F, El-Jissry M. (1991). Cyclopeptide alkaloids from Zizyphus spina-christi. Phytochemistry, 1991, 30(4), 1348-1349. [View]
Pubchem:
11953941
Cas:
55839-64-0
Zinc:
ZINC000004098504
Kegg Ligand:
C10016
Chebi:
10122
Nmrshiftdb2:
70080489
Comptox:
DTXSID40474625
No compound-protein relationship available.
SMILES: C1CNC(C12)C(=O)N3C(CCC3)C(=O)NC=Cc4ccc(O2)cc4
Level: 0
Mol. Weight: 597.76 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.92
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -5.0
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 9.47
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.79
- Plasma Protein Binding
- 73.03
- 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
- Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 10.43
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.46
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.97
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 6.92
- 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
- -16568.97
- Rat (Acute)
- 3.19
- Rat (Chronic Oral)
- 1.66
- Fathead Minnow
- 35.9
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 314.93
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 2.46
- Log(P)
- 2.43
- Log S
- -3.19
- Log(Vapor Pressure)
- -14.03
- Melting Point
- 201.45
- pKa Acid
- 6.6
- pKa Basic
- 7.58
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7819 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7747 |
| Purine nucleoside phosphorylase DeoD-type | O34925 | DEOD_BACSU | Bacillus subtilis | 3 | 0.7742 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7643 |
| Proton-gated ion channel | Q7NDN8 | GLIC_GLOVI | Gloeobacter violaceus | 3 | 0.7581 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7383 |
| Metallo-beta-lactamase type 2 | C7C422 | BLAN1_KLEPN | Klebsiella pneumoniae | 2 | 0.7370 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7341 |
| Corticosteroid-binding globulin | P08185 | CBG_HUMAN | Homo sapiens | 3 | 0.7314 |
| Flavin reductase like domain-containing protein | Q4UKE8 | Q4UKE8_RICFE | Rickettsia felis | 3 | 0.7280 |
| prolyl oligopeptidase | Q9X6R4 | Q9X6R4_AERCA | Aeromonas caviae | 3 | 0.7221 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7191 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7136 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 2 | 0.7134 |
| Norsolorinic acid synthase | Q12053 | AFLC_ASPPU | Aspergillus parasiticus | 3 | 0.7121 |
| Phospholipase A2, major isoenzyme | P00592 | PA21B_PIG | Sus scrofa | 3 | 0.7119 |
| Elongation factor Tu 1 | P0CE47 | EFTU1_ECOLI | Escherichia coli | 3 | 0.7074 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7047 |