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BASTADIN 13
ID: ALA445712
Max Phase: Preclinical
Molecular Formula: C34H28Br4N4O8
Molecular Weight: 940.23
Molecule Type: Small molecule
Associated Items:
Representations
Synonyms (1): Bastadin 13
Synonyms from Alternative Forms(1):
Canonical SMILES: O=C1NCCc2ccc(c(Br)c2)Oc2cc(ccc2O)CCNC(=O)/C(=N/O)Cc2cc(Br)c(O)c(c2)Oc2c(Br)cc(cc2Br)C/C1=N\O
Standard InChI: InChI=1S/C34H28Br4N4O8/c35-21-9-17-2-4-28(21)49-29-15-18(1-3-27(29)43)6-8-40-34(46)26(42-48)14-20-10-22(36)31(44)30(16-20)50-32-23(37)11-19(12-24(32)38)13-25(41-47)33(45)39-7-5-17/h1-4,9-12,15-16,43-44,47-48H,5-8,13-14H2,(H,39,45)(H,40,46)/b41-25+,42-26+
Standard InChI Key: XNGIESBQQZJDTL-RIVOPQIESA-N
Associated Targets(Human)
HUVEC 11049 Activities
Associated Targets(non-human)
Bacillus subtilis 32866 Activities
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Endothelin receptor ET-A 411 Activities
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Endothelin receptor ET-B 454 Activities
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Trypanosoma brucei brucei 13300 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: 940.23 | Molecular Weight (Monoisotopic): 935.8641 | AlogP: 7.51 | #Rotatable Bonds: 0 |
| Polar Surface Area: 182.30 | Molecular Species: NEUTRAL | HBA: 10 | HBD: 6 |
| #RO5 Violations: 3 | HBA (Lipinski): 12 | HBD (Lipinski): 6 | #RO5 Violations (Lipinski): 4 |
| CX Acidic pKa: 6.96 | CX Basic pKa: | CX LogP: 8.20 | CX LogD: 7.47 |
| Aromatic Rings: 4 | Heavy Atoms: 50 | QED Weighted: 0.08 | Np Likeness Score: 1.18 |
References
| 1. Pettit GR, Butler MS, Bass CG, Doubek DL, Williams MD, Schmidt JM, Pettit RK, Hooper JN, Tackett LP, Filiatrault MJ.. (1995) Antineoplastic agents, 326. The stereochemistry of bastadins 8, 10, and 12 from the Bismarck archipelago marine sponge Ianthella basta., 58 (5): [PMID:7623047] [10.1021/np50119a005] |
| 2. Gulavita NK, Wright AE, McCarthy PJ, Pomponi SA, Kelly-Borges M, Chin M, Sills MA.. (1993) Isolation and structure elucidation of 34-sulfatobastadin 13, an inhibitor of the endothelin A receptor, from a marine sponge of the genus Ianthella., 56 (9): [PMID:8254355] [10.1021/np50099a026] |
| 3. Calcul L, Inman WD, Morris AA, Tenney K, Ratnam J, McKerrow JH, Valeriote FA, Crews P.. (2010) Additional insights on the bastadins: isolation of analogues from the sponge Ianthella cf. reticulata and exploration of the oxime configurations., 73 (3): [PMID:20102170] [10.1021/np9005986] |
| 4. Bedos-Belval F, Rouch A, Vanucci-Bacque C, Baltas M. (2012) Diaryl ether derivatives as anticancer agents a review, 3 (11): [10.1039/C2MD20199B] |
Source
Source(1):