helvolic acid   Click here for help

GtoPdb Ligand ID: 12329

Synonyms: fumigacin
Compound class: Natural product or derivative
Comment: Helvolic acid was originally isolated from the culture medium of Aspergillus fumigatus [1,3]. It is a fusidane antibacterial compound with activity against Gram-positive bacteria.
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 CDK toolkit. 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 8
Hydrogen bond donors 1
Rotatable bonds 8
Topological polar surface area 124.04
Molecular weight 568.3
XLogP 4.34
No. Lipinski's rules broken 0
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.

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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(=O)[C@@H](OC(=O)C)[C@@H]2[C@]1(C)C=CC(=O)[C@H]2C)C
Isomeric SMILES C[C@H]1[C@@H]2[C@@H](C(=O)[C@]3([C@H]([C@]2(C=CC1=O)C)CC[C@@H]1[C@@]3(C[C@@H](/C/1=C(/CCC=C(C)C)\C(=O)O)OC(=O)C)C)C)OC(=O)C
InChI InChI=1S/C33H44O8/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/h10,14-15,18,22,24-25,27-28H,9,11-13,16H2,1-8H3,(H,38,39)/b26-21-/t18-,22+,24+,25+,27-,28+,31-,32+,33-/m1/s1
InChI Key MDFZYGLOIJNNRM-OAJDADRGSA-N
Classification Click here for help
Compound class Natural product or derivative
IUPAC Name Click here for help
(2Z)-2-[(4S,5S,6S,8S,9S,10R,13R,14S,16S)-6,16-diacetyloxy-4,8,10,14-tetramethyl-3,7-dioxo-5,6,9,11,12,13,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid
Synonyms Click here for help
fumigacin
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo Helvolic acid, fumigacin
Other databases
CAS Registry No. 29400-42-8 (source: Scifinder)
ChEBI CHEBI:62460
ChEMBL Ligand CHEMBL505132
GtoPdb PubChem SID 479821120
PubChem CID 3002143
Search Google for chemical match using the InChIKey MDFZYGLOIJNNRM-OAJDADRGSA-N
Search Google for chemicals with the same backbone MDFZYGLOIJNNRM
UniChem Compound Search for chemical match using the InChIKey MDFZYGLOIJNNRM-OAJDADRGSA-N
UniChem Connectivity Search for chemical match using the InChIKey MDFZYGLOIJNNRM-OAJDADRGSA-N