NP-MRD: Showing NP-Card for fusidic acid (NP0266354)

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Record Information

Version

2.0

Created at

2022-09-08 10:40:35 UTC

Updated at

2022-09-08 10:40:35 UTC

NP-MRD ID

NP0266354

Secondary Accession Numbers

None

Natural Product Identification

Common Name

fusidic acid

Description

Fusidic Acid, also known as fusidate or fucidin acid, 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. Thus, fusidic Acid is considered to be an isoprenoid lipid molecule. Fusidic Acid is a drug which is used for the treatment of bacterial infections. Fusidic Acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. fusidic acid is found in Apis cerana, Epidermophyton floccosum and Stilbella aciculosa. fusidic acid was first documented in 2000 (PMID: 11413487). A steroid antibiotic that is isolated from the fermentation broth of Fusidium coccineum (PMID: 11412963).

Structure

MOL 3D MOL SDF PDB SMILES InChI

2703
  Mrv0541 02231216232D          

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M  END

     RDKit          3D

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M  END

2703
  Mrv0541 02231216232D          

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    6.8232   -2.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3678   -0.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8148   -1.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8079   -2.6408    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5863   -3.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5779    0.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0270    1.1170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3851    0.6732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0404   -1.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2832    1.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8655   -1.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7323    2.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9886    3.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4376    3.9134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7958    3.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6836   -1.0275    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3573   -3.2949    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6109    0.1238    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 14  1  1  6  0  0  0
 22  2  1  1  0  0  0
  2 31  1  0  0  0  0
 26  3  1  6  0  0  0
  4 30  1  0  0  0  0
  5 30  2  0  0  0  0
  6 31  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 13  1  0  0  0  0
  7 20  1  6  0  0  0
  8 10  1  0  0  0  0
  8 14  1  0  0  0  0
  8 38  1  1  0  0  0
  9 12  1  0  0  0  0
  9 17  1  0  0  0  0
  9 23  1  1  0  0  0
 10 11  1  0  0  0  0
 10 18  1  0  0  0  0
 10 24  1  1  0  0  0
 11 15  1  0  0  0  0
 11 19  1  0  0  0  0
 11 39  1  6  0  0  0
 12 16  1  0  0  0  0
 12 21  1  0  0  0  0
 12 40  1  6  0  0  0
 13 15  1  0  0  0  0
 14 16  1  0  0  0  0
 17 22  1  0  0  0  0
 18 25  1  0  0  0  0
 19 26  1  0  0  0  0
 19 27  1  6  0  0  0
 21 22  1  0  0  0  0
 21 28  2  0  0  0  0
 25 26  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 29 32  1  0  0  0  0
 31 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0266354

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C31H48O6

> <MOLECULAR_WEIGHT>
516.7092

> <EXACT_MASS>
516.345089268

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
59.7651047711296

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
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

> <ALOGPS_LOGP>
4.97

> <JCHEM_LOGP>
4.4219138163333325

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.892605767976843

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.664285160917447

> <JCHEM_PKA_STRONGEST_BASIC>
-0.20031955057054518

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
144.1233

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
discoid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2703                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.209  -0.224   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      16.106  -1.764   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.905  -5.694   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      16.131   2.720   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      16.681   0.110   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      16.106  -4.431   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      10.876  -3.304   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.543  -2.534   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.210  -2.534   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.141  -3.315   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.129  -4.919   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.210  -0.994   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.901  -4.908   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.543  -0.994   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.518  -5.721   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.876  -0.224   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.667  -3.003   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.714  -2.446   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.688  -5.765   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.866  -4.484   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.667  -0.525   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.566  -1.764   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.737  -3.981   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.153  -1.775   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.254  -3.259   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.241  -4.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.694  -7.305   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.145   0.939   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.117   2.085   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.652   1.257   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.875  -3.098   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.595   3.549   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.416  -3.098   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.567   4.695   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.045   6.159   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.017   7.305   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      14.552   6.476   0.000  0.00  0.00           C+0
HETATM   38  H   UNK     0      10.609  -1.918   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0       8.134  -6.150   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0      12.340   0.231   0.000  0.00  0.00           H+0
CONECT    1   14                                                            
CONECT    2   22   31                                                       
CONECT    3   26                                                            
CONECT    4   30                                                            
CONECT    5   30                                                            
CONECT    6   31                                                            
CONECT    7    8    9   13   20                                             
CONECT    8    7   10   14   38                                             
CONECT    9    7   12   17   23                                             
CONECT   10    8   11   18   24                                             
CONECT   11   10   15   19   39                                             
CONECT   12    9   16   21   40                                             
CONECT   13    7   15                                                       
CONECT   14    1    8   16                                                  
CONECT   15   11   13                                                       
CONECT   16   12   14                                                       
CONECT   17    9   22                                                       
CONECT   18   10   25                                                       
CONECT   19   11   26   27                                                  
CONECT   20    7                                                            
CONECT   21   12   22   28                                                  
CONECT   22    2   17   21                                                  
CONECT   23    9                                                            
CONECT   24   10                                                            
CONECT   25   18   26                                                       
CONECT   26    3   19   25                                                  
CONECT   27   19                                                            
CONECT   28   21   29   30                                                  
CONECT   29   28   32                                                       
CONECT   30    4    5   28                                                  
CONECT   31    2    6   33                                                  
CONECT   32   29   34                                                       
CONECT   33   31                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38    8                                                            
CONECT   39   11                                                            
CONECT   40   12                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

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 Mass

516.7092 Da

Monoisotopic Mass

516.34509 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Epidermophyton floccosum	LOTUS Database	35616633
Stilbella aciculosa	LOTUS Database	35616633

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0015570

DrugBank ID

DB02703

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Fusidic_acid

METLIN ID

Not Available

PubChem Compound

3000226

PDB ID

FUA

ChEBI ID

29013

Good Scents ID

Not Available

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Kuznetsova TA, Smetanina OF, Afiyatullov SS, Pivkin MV, Denisenko VA, Elyakov GB: The identification of fusidic acid, a steroidal antibiotic from marine isolate of the fungus Stilbella aciculosa. Biochem Syst Ecol. 2001 Aug;29(8):873-874. doi: 10.1016/s0305-1978(00)00102-2. [PubMed:11412963 ]
LOTUS database [Link]

Showing NP-Card for fusidic acid (NP0266354)

MOL for NP0266354 (fusidic acid)

3D MOL for NP0266354 (fusidic acid)

3D SDF for NP0266354 (fusidic acid)

3D-SDF for NP0266354 (fusidic acid)

PDB for NP0266354 (fusidic acid)

3D PDB for NP0266354 (fusidic acid)

SMILES for NP0266354 (fusidic acid)

INCHI for NP0266354 (fusidic acid)

Structure for NP0266354 (fusidic acid)

3D Structure for NP0266354 (fusidic acid)