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DIAZEPINOMICIN
ID: ALA550961
Max Phase: Phase
Molecular Formula: C28H34N2O4
Molecular Weight: 462.59
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (5): Amo-01 | Diazepinomicin | BU-4664L | ECO-4601 | TLN-4601
Synonyms from Alternative Forms(5):
Canonical SMILES: CC(C)=CCC/C(C)=C/CC/C(C)=C/CN1C(=O)c2cccc(O)c2Nc2c(O)cc(O)cc21
Standard InChI: InChI=1S/C28H34N2O4/c1-18(2)8-5-9-19(3)10-6-11-20(4)14-15-30-23-16-21(31)17-25(33)27(23)29-26-22(28(30)34)12-7-13-24(26)32/h7-8,10,12-14,16-17,29,31-33H,5-6,9,11,15H2,1-4H3/b19-10+,20-14+
Standard InChI Key: SALVHVNECODMJP-GNUCVDFRSA-N
Associated Targets(Human)
HUVEC (11049 Activities)
MMP2 Tchem Matrix metalloproteinase-2 (6627 Activities)
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MMP9 Tchem Matrix metalloproteinase 9 (6779 Activities)
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PC-3 (62116 Activities)
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NCI-H460 (60772 Activities)
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Associated Targets(non-human)
Staphylococcus aureus (210822 Activities)
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Enterococcus faecium (13803 Activities)
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Escherichia coli (133304 Activities)
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Candida albicans (78123 Activities)
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Renca (39 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: Yes | 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: 462.59 | Molecular Weight (Monoisotopic): 462.2519 | AlogP: 6.93 | #Rotatable Bonds: 8 |
| Polar Surface Area: 93.03 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 4 |
| #RO5 Violations: 1 | HBA (Lipinski): 6 | HBD (Lipinski): 4 | #RO5 Violations (Lipinski): 1 |
| CX Acidic pKa: 8.88 | CX Basic pKa: 0.73 | CX LogP: 7.47 | CX LogD: 7.45 |
| Aromatic Rings: 2 | Heavy Atoms: 34 | QED Weighted: 0.19 | Np Likeness Score: 1.36 |
References
| 1. Ratnayake AS, Janso JE, Feng X, Schlingmann G, Goljer I, Carter GT.. (2009) Evaluating indole-related derivatives as precursors in the directed biosynthesis of diazepinomicin analogues., 72 (3): [PMID:19199816] [10.1021/np800664u] |
| 2. Miyanaga S, Sakurai H, Saiki I, Onaka H, Igarashi Y.. (2010) Anti-invasive and anti-angiogenic activities of naturally occurring dibenzodiazepine BU-4664L and its derivatives., 20 (3): [PMID:20056543] [10.1016/j.bmcl.2009.12.055] |
| 3. Unpublished dataset, |
| 4. Liu C, Xu YY, Wen ZH, Dong YH, Liu ZP.. (2022) Synthesis and biological evaluation of BU-4664L derivatives as potential anticancer agents., 55 [PMID:34838651] [10.1016/j.bmcl.2021.128474] |
Source
Source(2):