Bis1   Click here for help

GtoPdb Ligand ID: 9572

Synonyms: Tz‐BBA
Compound class: Natural product
Comment: Bis1 is a thiazole analogue of the marine cyanobacterium‐derived linear amide, bisebromoamide (BBA; PubChem CID 44520348) [1]. BBA is a nonribosomal peptide that is synthesised in cyanobacteria in a process involving nonribosomal peptide synthetase (NRPS) enzyme complexes.

The IUPAC condensed name for this peptide is pivaloyl-Ala-N(Me)D-Tyr(3-Br)-Unk-D-Leu-N(Me)Phe-Pro-Et.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 14
Hydrogen bond donors 3
Rotatable bonds 25
Topological polar surface area 214.4
Molecular weight 1007.42
XLogP 5.08
No. Lipinski's rules broken 3

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCC(=O)C1CCCN1C(=O)C(N(C(=O)C(NC(=O)C1CSC(=N1)C1CC(CN1C(=O)C(N(C(=O)C(NC(=O)C(C)(C)C)C)C)Cc1ccc(c(c1)Br)O)C)CC(C)C)C)Cc1ccccc1
Isomeric SMILES CCC(=O)[C@@H]1CCCN1C(=O)[C@@H](N(C(=O)[C@H](NC(=O)[C@H]1CSC(=N1)[C@@H]1C[C@@H](CN1C(=O)[C@H](N(C(=O)[C@@H](NC(=O)C(C)(C)C)C)C)Cc1ccc(c(c1)Br)O)C)CC(C)C)C)Cc1ccccc1
InChI InChI=1S/C50H70BrN7O8S/c1-11-41(59)37-18-15-21-57(37)47(64)39(25-32-16-13-12-14-17-32)56(10)46(63)35(22-29(2)3)53-43(61)36-28-67-44(54-36)38-23-30(4)27-58(38)48(65)40(26-33-19-20-42(60)34(51)24-33)55(9)45(62)31(5)52-49(66)50(6,7)8/h12-14,16-17,19-20,24,29-31,35-40,60H,11,15,18,21-23,25-28H2,1-10H3,(H,52,66)(H,53,61)/t30-,31-,35+,36+,37-,38-,39-,40+/m0/s1
InChI Key ADHYVMBQQIBLSN-WQGIEDEVSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Johnston HJ, Boys SK, Makda A, Carragher NO, Hulme AN. (2016)
Naturally Inspired Peptide Leads: Alanine Scanning Reveals an Actin-Targeting Thiazole Analogue of Bisebromoamide.
Chembiochem, 17 (17): 1621-7. [PMID:27304907]