Bis1   

GtoPdb Ligand ID: 9572

Synonyms: Tz‐BBA
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
Click here for structure editor
Physico-chemical Properties
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
SMILES / InChI / InChIKey
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
Classification
Compound class Natural product or derivative
IUPAC Name
(2S)-1-[N-[[(4S)-2-[(2S)-1-(N-Pivaloyl-L-Ala-N-methyl-3-bromo-D-Tyr-)-4alpha-methylpyrrolidine-2alpha-yl]-2-thiazoline-4beta-yl]carbonyl]-D-Leu-N-methyl-L-Phe-]-2alpha-propanoylpyrrolidine
Synonyms
Tz‐BBA
Database Links
GtoPdb PubChem SID 336446958
PubChem CID 101500806
Search Google for chemical match using the InChIKey ADHYVMBQQIBLSN-WQGIEDEVSA-N
Search Google for chemicals with the same backbone ADHYVMBQQIBLSN
Search UniChem for chemical match using the InChIKey ADHYVMBQQIBLSN-WQGIEDEVSA-N
Search UniChem for chemicals with the same backbone ADHYVMBQQIBLSN