cephalosporin P1   Click here for help

GtoPdb Ligand ID: 12330

Synonyms: acremonic acid
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
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Physico-chemical Properties
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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
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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
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
(2Z)-2-[(3R,4S,5S,6R,7R,8S,9S,10R,13R,14S,16S)-6,16-diacetyloxy-3,7-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid
Synonyms Click here for help
acremonic acid
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Cephalosporin P1
Other databases
CAS Registry No. 13258-72-5 (source: Scifinder)
ChEMBL Ligand CHEMBL3401949
GtoPdb PubChem SID 479821121
PubChem CID 3037114
Search Google for chemical match using the InChIKey YJJWILCYIMMPAS-VALXSNPUSA-N
Search Google for chemicals with the same backbone YJJWILCYIMMPAS
UniChem Compound Search for chemical match using the InChIKey YJJWILCYIMMPAS-VALXSNPUSA-N
UniChem Connectivity Search for chemical match using the InChIKey YJJWILCYIMMPAS-VALXSNPUSA-N