cephalosporin P1   Click here for help

GtoPdb Ligand ID: 12330

Synonyms: acremonic acid
Compound class: Natural product
Comment: Cephalosporin P1 is the main active component in cephalosporin P, a fungal metabolite isolated from the culture broth of Acremonium chrysogenum (formerly known as Cephalosporium) [1]. It is a fusidane antibacterial compound.
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 8
Topological polar surface area 130.36
Molecular weight 574.35
XLogP 5.4
No. Lipinski's rules broken 1

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
Click here for help

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/)

✖
Canonical SMILES CC(=O)O[C@H]1C[C@]2([C@H](/C/1=C(/C(=O)O)\CCC=C(C)C)CC[C@@H]1[C@]2(C)[C@@H](O)[C@H](OC(=O)C)[C@@H]2[C@]1(C)CC[C@H]([C@H]2C)O)C
Isomeric SMILES C[C@@H]1[C@@H](CC[C@]2([C@H]1[C@H]([C@@H]([C@]1([C@H]2CC[C@@H]2[C@@]1(C[C@@H](/C/2=C(/CCC=C(C)C)\C(=O)O)OC(=O)C)C)C)O)OC(=O)C)C)O
InChI InChI=1S/C33H50O8/c1-17(2)10-9-11-21(30(38)39)26-22-12-13-25-31(6)15-14-23(36)18(3)27(31)28(41-20(5)35)29(37)33(25,8)32(22,7)16-24(26)40-19(4)34/h10,18,22-25,27-29,36-37H,9,11-16H2,1-8H3,(H,38,39)/b26-21-/t18-,22+,23-,24+,25+,27-,28-,29+,31-,32+,33-/m1/s1
InChI Key YJJWILCYIMMPAS-VALXSNPUSA-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. Burton HS, Abraham EP. (1951)
Isolation of antibiotics from a species of Cephalosporium; cephalosporins P1, P2, P3, P4, and P5.
Biochem J, 50 (2): 168-74. [PMID:14904388]
2. O'Neill AJ, Bostock JM, Moita AM, Chopra I. (2002)
Antimicrobial activity and mechanisms of resistance to cephalosporin P1, an antibiotic related to fusidic acid.
J Antimicrob Chemother, 50 (6): 839-48. [PMID:12461002]
3. Ritchie AC, Smith N, Florey HW. (1951)
Some biological properties of cephalosporin P1.
Br J Pharmacol Chemother, 6 (3): 430-44. [PMID:14878978]