ChemFOnt: Showing chemical card for Fusidic Acid (CFc000009832)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:57:05 UTC

Chemfont ID

CFc000009832

Molecule Identification

Common Name

Fusidic Acid

Definition

Fusidic Acid is only found in individuals that have used or taken this drug. It is an antibiotic isolated from the fermentation broth of Fusidium coccineum. (From Merck Index, 11th ed) It acts by inhibiting translocation during protein synthesis.Fusidic acid works by interfering with bacterial protein synthesis, specifically by preventing the translocation of the elongation factor G (EF-G) from the ribosome. It also can inhibit chloramphenicol acetyltransferase enzymes.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Fucidic acid	ChEBI
Fucidin acid	ChEBI
Fusidine	ChEBI
Ramycin	ChEBI
FA	Kegg
Fucidate	Generator
Fusidate	Generator
Diethanolamine fusidate	HMDB
Fusidate sodium	HMDB
Fusidate, sodium	HMDB
Sodium fusidate	HMDB
Acid, fusidic	HMDB
Fucithalmic	HMDB
Fusidate, silver	HMDB
Fusidic acid, sodium salt	HMDB
Sodium, fusidate	HMDB
Fusidin	HMDB
Silver fusidate	HMDB
Stanicide	HMDB
(-)-Fusidate	HMDB
Fusidic acid	MeSH

Chemical Formula

C₃₁H₄₈O₆

Average Molecular Weight

516.7092

Monoisotopic Molecular Weight

516.345089268

IUPAC Name

2-[(1S,2S,5R,6S,7S,10S,11S,13S,14Z,15R,17R)-13-(acetyloxy)-5,17-dihydroxy-2,6,10,11-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-ylidene]-6-methylhept-5-enoic acid

Traditional Name

discoid

CAS Registry Number

6990-06-3

SMILES

O[C@@H]1CC[C@@]2(C)[C@@]([H])(CC[C@@]3(C)[C@@]2([H])[C@H](O)C[C@@]2([H])\C([C@@H](OC(=O)C)C[C@]32C)=C(/CCC=C(C)C)C(O)=O)[C@@H]1C

InChI Identifier

InChI=1S/C31H48O6/c1-17(2)9-8-10-20(28(35)36)26-22-15-24(34)27-29(5)13-12-23(33)18(3)21(29)11-14-30(27,6)31(22,7)16-25(26)37-19(4)32/h9,18,21-25,27,33-34H,8,10-16H2,1-7H3,(H,35,36)/b26-20-/t18-,21-,22-,23+,24+,25-,27-,29-,30-,31-/m0/s1

InChI Key

IECPWNUMDGFDKC-MZJAQBGESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid esters

Direct Parent

Steroid esters

Alternative Parents

Substituents

Steroid ester
3-hydroxysteroid
3-alpha-hydroxysteroid
11-hydroxysteroid
11-alpha-hydroxysteroid
Hydroxysteroid
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Alcohol
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3alpha-hydroxy steroid (CHEBI:29013 )
alpha,beta-unsaturated monocarboxylic acid (CHEBI:29013 )
sterol ester (CHEBI:29013 )
steroid acid (CHEBI:29013 )
11alpha-hydroxy steroid (CHEBI:29013 )
steroid antibiotic (CHEBI:29013 )
Prostostane and fusidane triterpenoids (LMPR0106040001 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0015570)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0052 g/L	ALOGPS
logP	4.97	ALOGPS
logP	4.42	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.66	ChemAxon
pKa (Strongest Basic)	-0.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	144.12 m³·mol⁻¹	ChemAxon
Polarizability	59.77 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon