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ARCHAZOLID B
ID: ALA411767
Max Phase: Preclinical
Molecular Formula: C41H60N2O7S
Molecular Weight: 725.01
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CNC(=O)O[C@@H](CC(C)C)c1nc([C@H]2OC(=O)/C=C/C/C(C)=C/[C@@H](O)[C@@H](C)/C=C(C)\C=C(C)/C=C/[C@@H](O)[C@H](C)[C@H](OC)/C(C)=C/C=C/[C@@H]2C)cs1
Standard InChI: InChI=1S/C41H60N2O7S/c1-25(2)20-36(49-41(47)42-10)40-43-33(24-51-40)39-30(7)16-13-15-29(6)38(48-11)32(9)34(44)19-18-27(4)21-28(5)22-31(8)35(45)23-26(3)14-12-17-37(46)50-39/h12-13,15-19,21-25,30-32,34-36,38-39,44-45H,14,20H2,1-11H3,(H,42,47)/b16-13+,17-12+,19-18+,26-23+,27-21-,28-22-,29-15+/t30-,31-,32-,34+,35+,36-,38+,39-/m0/s1
Standard InChI Key: BYVUBCIRZIXXCV-OZCJWKDYSA-N
Associated Targets(Human)
ELANE Tclin Leukocyte elastase (8173 Activities)
ADORA3 Tchem Adenosine A3 receptor (15931 Activities)
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P2RX3 Tclin P2X purinoceptor 3 (1991 Activities)
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PRSS1 Tclin Trypsin (2137 Activities)
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CTSB Tchem Cathepsin B (3822 Activities)
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CTSL Tclin Cathepsin L (3852 Activities)
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CTRC Tchem Chymotrypsin (134 Activities)
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CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
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CYP2B6 Tchem Cytochrome P450 2B6 (1338 Activities)
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CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
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CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
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CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
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Associated Targets(non-human)
L929 (3802 Activities)
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VHA55 V-type proton ATPase subunit B (6 Activities)
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Molecule Features
| Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
| Molecule Type: Small molecule | Topical: No | First In Class: No | Black Box: No |
| Chirality: No | Availability: No | Prodrug: No |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Properties
| Molecular Weight: 725.01 | Molecular Weight (Monoisotopic): 724.4121 | AlogP: 8.67 | #Rotatable Bonds: 6 |
| Polar Surface Area: 127.21 | Molecular Species: NEUTRAL | HBA: 9 | HBD: 3 |
| #RO5 Violations: 2 | HBA (Lipinski): 9 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 2 |
| CX Acidic pKa: | CX Basic pKa: 0.78 | CX LogP: 7.85 | CX LogD: 7.85 |
| Aromatic Rings: 1 | Heavy Atoms: 51 | QED Weighted: 0.20 | Np Likeness Score: 1.57 |
References
| 1. Menche D, Hassfeld J, Sasse F, Huss M, Wieczorek H.. (2007) Design, synthesis, and biological evaluation of novel analogues of archazolid: a highly potent simplified V-ATPase inhibitor., 17 (6): [PMID:17239591] [10.1016/j.bmcl.2006.12.073] |
| 2. Horstmann N, Essig S, Bockelmann S, Wieczorek H, Huss M, Sasse F, Menche D.. (2011) Archazolid A-15-O-β-D-glucopyranoside and iso-archazolid B: potent V-ATPase inhibitory polyketides from the myxobacteria Cystobacter violaceus and Archangium gephyra., 74 (5): [PMID:21513292] [10.1021/np200036v] |
| 3. Scheeff S, Rivière S, Ruiz J, Abdelrahman A, Schulz-Fincke AC, Köse M, Tiburcy F, Wieczorek H, Gütschow M, Müller CE, Menche D.. (2020) Synthesis of Novel Potent Archazolids: Pharmacology of an Emerging Class of Anticancer Drugs., 63 (4): [PMID:31990540] [10.1021/acs.jmedchem.9b01887] |
Source
Source(1):