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Jubanine A
- Family: Plantae - Rhamnaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Cyclopeptide Alkaloid
| Canonical Smiles | CCC(C1NC(=O)C2C(CCN2C(=O)C(Cc2ccccc2)NC(=O)C(N(C)C)Cc2ccccc2)Oc2cc(/C=C\NC1=O)c(OC)cc2)C |
|---|---|
| InChI | InChI=1S/C40H49N5O6/c1-6-26(2)35-38(47)41-21-19-29-25-30(17-18-33(29)50-5)51-34-20-22-45(36(34)39(48)43-35)40(49)31(23-27-13-9-7-10-14-27)42-37(46)32(44(3)4)24-28-15-11-8-12-16-28/h7-19,21,25-26,31-32,34-36H,6,20,22-24H2,1-5H3,(H,41,47)(H,42,46)(H,43,48)/b21-19- |
| InChIKey | YDFMRHVTUVJMHS-VZCXRCSSSA-N |
| Formula | C40H49N5O6 |
| HBA | 7 |
| HBD | 3 |
| MW | 695.86 |
| Rotatable Bonds | 11 |
| TPSA | 129.31 |
| LogP | 3.58 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 51 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.4 |
| Exact Mass | 695.37 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ziziphus spina-christi | Rhamnaceae | Plantae | 264981 |
Showing of synonyms
Jubanine A
- Abdel-galil F, El-Jissry M. (1991). Cyclopeptide alkaloids from Zizyphus spina-christi. Phytochemistry, 1991, 30(4), 1348-1349. [View]
No compound-protein relationship available.
SMILES: c1ccccc1CCC(=O)NC(Cc2ccccc2)C(=O)N(CC3)C(C34)C(=O)NCC(=O)NC=Cc5cc(O4)ccc5
Level: 2
Mol. Weight: 695.86 g/mol
SMILES: c1ccccc1CCC(=O)NCC(=O)N(CC2)C(C23)C(=O)NCC(=O)NC=Cc4cc(O3)ccc4
Level: 1
Mol. Weight: 695.86 g/mol
SMILES: c1ccccc1CCC(=O)N(CC2)C(C23)C(=O)NCC(=O)NC=Cc4cc(O3)ccc4
Level: 1
Mol. Weight: 695.86 g/mol
SMILES: c1ccccc1CCC(=O)NCCc2ccccc2
Level: 1
Mol. Weight: 695.86 g/mol
SMILES: C1CNC(C12)C(=O)NCC(=O)NC=Cc3cc(O2)ccc3
Level: 0
Mol. Weight: 695.86 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 695.86 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.5
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -0.43
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 628.81
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.26
- Plasma Protein Binding
- 53.58
- 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
- Inhibitor
- CYP 2C19 Substrate
- Non-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
- Inhibitor
Excretion
- Clearance
- 12.47
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -14.56
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.05
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 9.34
- 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
- -1141576.31
- Rat (Acute)
- 2.83
- Rat (Chronic Oral)
- 1.64
- Fathead Minnow
- 1445.66
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Toxic
- SR-p53
- Safe
General Properties
- Boiling Point
- 123913.49
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- 4.29
- Log(P)
- 4.24
- Log S
- -4.01
- Log(Vapor Pressure)
- -4050.78
- Melting Point
- 210.78
- pKa Acid
- -1.79
- pKa Basic
- 7.67
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Interstitial collagenase | P03956 | MMP1_HUMAN | Homo sapiens | 4 | 0.9677 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.9463 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 3 | 0.9244 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.9216 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 3 | 0.9179 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.9042 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.8969 |
| Bifunctional protein GlmU | P43889 | GLMU_HAEIN | Haemophilus influenzae | 3 | 0.8903 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.8687 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 3 | 0.8638 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.8558 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8474 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8306 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 2 | 0.8220 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.8028 |
| Matrix metalloproteinase-20 | O60882 | MMP20_HUMAN | Homo sapiens | 3 | 0.8011 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 3 | 0.7992 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7922 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7812 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7794 |
| Orf1ab polyprotein | Q6T1E9 | Q6T1E9_CVHSA | SARS coronavirus CUHK-L2 | 3 | 0.7789 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7751 |
| DNA topoisomerase 4 subunit B | H7C794 | PARE_ENTFA | Enterococcus faecalis | 2 | 0.7730 |
| Polymerase acidic protein | P03433 | PA_I34A1 | Influenza A virus | 2 | 0.7711 |
| Coagulation factor X | P00742 | FA10_HUMAN | Homo sapiens | 3 | 0.7708 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7704 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7696 |
| Annexin A5 | P08758 | ANXA5_HUMAN | Homo sapiens | 2 | 0.7672 |
| clade A/E 93TH057 HIV-1 gp120 core | A0A0M3KKW9 | A0A0M3KKW9_9HIV1 | Human immunodeficiency virus 1 | 3 | 0.7657 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7621 |
| Poly [ADP-ribose] polymerase 1 | P09874 | PARP1_HUMAN | Homo sapiens | 3 | 0.7591 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 2 | 0.7589 |
| Caffeoyl-CoA O-methyltransferase | Q40313 | CAMT_MEDSA | Medicago sativa | 3 | 0.7552 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7548 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7543 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7513 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7497 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 2 | 0.7474 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7470 |
| Gag-Pol polyprotein | P04584 | POL_HV2RO | Human immunodeficiency virus type 2 subtype A | 3 | 0.7446 |
| Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7410 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7407 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7380 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7331 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7329 |
| Stromelysin-1 | P08254 | MMP3_HUMAN | Homo sapiens | 3 | 0.7329 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7311 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7279 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7278 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7275 |
| Kelch-like ECH-associated protein 1 | Q14145 | KEAP1_HUMAN | Homo sapiens | 3 | 0.7273 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.7253 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7240 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7226 |
| Tryptase alpha/beta-1 | Q15661 | TRYB1_HUMAN | Homo sapiens | 3 | 0.7218 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7209 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 2 | 0.7194 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7185 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7177 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7170 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7160 |
| Decaprenylphosphoryl-beta-D-ribose oxidase | I6X8C4 | I6X8C4_MYCTU | Mycobacterium tuberculosis | 3 | 0.7159 |
| Urokinase-type plasminogen activator | P00749 | UROK_HUMAN | Homo sapiens | 3 | 0.7158 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7130 |
| Cruzipain | P25779 | CYSP_TRYCR | Trypanosoma cruzi | 4 | 0.7124 |
| Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 2 | 0.7076 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7073 |
| Cytochrome P450 | S6BVH1 | S6BVH1_RHOER | Rhodococcus erythropolis | 3 | 0.7065 |
| Subunit alpha of sarocosine oxidase | Q50LF0 | Q50LF0_9CORY | Corynebacterium sp. U-96 | 3 | 0.7063 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7059 |
| Cytosol aminopeptidase | O86436 | AMPA_PSEPU | Pseudomonas putida | 3 | 0.7058 |
| Histone-lysine N-methyltransferase SETD7 | Q8WTS6 | SETD7_HUMAN | Homo sapiens | 4 | 0.7039 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7037 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 2 | 0.7033 |
| Uncharacterized protein | Q55S71 | Q55S71_CRYNB | Cryptococcus neoformans var. neoformans serotype D | 3 | 0.7032 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 2 | 0.7017 |
| Histidinol dehydrogenase | P06988 | HISX_ECOLI | Escherichia coli | 2 | 0.7011 |
| L-lactate dehydrogenase A chain | P04642 | LDHA_RAT | Rattus norvegicus | 3 | 0.7005 |