NP-MRD: Showing NP-Card for 3-Ketofusidic acid (NP0062186)

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Record Information

Version

2.0

Created at

2022-04-28 06:50:42 UTC

Updated at

2022-04-28 06:50:42 UTC

NP-MRD ID

NP0062186

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Ketofusidic acid

Description

11-Keto fuidic Acid, also known as 11-keto fuidate, 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. 3-Ketofusidic acid is found in Epidermophyton floccosum 8051 and Fusidium coccineum. Based on a literature review very few articles have been published on 11-Keto fuidic Acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208502D          

 37 40  0  0  1  0            999 V2000
    4.2475    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1838    0.8922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.0914    1.8134    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  9 35  1  1  0  0  0
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  4 37  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304282208502D          

 37 40  0  0  1  0            999 V2000
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    1.2487    0.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    2.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2763   -0.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  6  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  1  0  0  0
 15 16  2  0  0  0  0
 13 17  1  6  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 17 28  1  0  0  0  0
 28 29  1  0  0  0  0
 12 29  1  0  0  0  0
 28 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 12 34  1  6  0  0  0
  9 35  1  1  0  0  0
  6 36  1  6  0  0  0
  4 37  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0062186

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@@H]2CC[C@@]3(C)[C@@H](C(=O)C[C@H]4\C([C@H](C[C@]34C)OC(C)=O)=C(/CCC=C(C)C)C(O)=O)[C@@]2(C)CCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H44O6/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/h9,18,21-22,25,27H,8,10-16H2,1-7H3,(H,35,36)/b26-20-/t18-,21-,22-,25-,27-,29-,30-,31-/m0/s1

> <INCHI_KEY>
XHWNFPOLQYKPKS-CNZZPSATSA-N

> <FORMULA>
C31H44O6

> <MOLECULAR_WEIGHT>
512.687

> <EXACT_MASS>
512.313789137

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
58.48438996336566

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1S,2S,6S,7S,10S,11S,13S,14Z,15R)-13-(acetyloxy)-2,6,10,11-tetramethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-ylidene]-6-methylhept-5-enoic acid

> <ALOGPS_LOGP>
4.71

> <JCHEM_LOGP>
5.192942323666665

> <ALOGPS_LOGS>
-5.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.65271800958531

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.606770709866654

> <JCHEM_PKA_STRONGEST_BASIC>
-6.765456127254188

> <JCHEM_POLAR_SURFACE_AREA>
97.74000000000001

> <JCHEM_REFRACTIVITY>
142.27290000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1S,2S,6S,7S,10S,11S,13S,14Z,15R)-13-(acetyloxy)-2,6,10,11-tetramethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-ylidene]-6-methylhept-5-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       9.968   2.301   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.943   1.666   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.374   6.011   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.138   4.882   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -4.083   6.098   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -3.718   3.456   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.032   6.519   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.494   6.730   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.074   8.156   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.599   8.367   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.180   9.794   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.545   7.151   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.179   1.534   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.544   1.875   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.815   0.359   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.637  -0.634   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.263  -0.165   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.764   0.984   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.331   0.781   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.897   4.562   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.982  -0.054   0.000  0.00  0.00           C+0
CONECT    1    2    7                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   37                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7    8   36                                             
CONECT    7    6    1                                                       
CONECT    8    6    9   15                                                  
CONECT    9    8   10   12   35                                             
CONECT   10    9   11                                                       
CONECT   11   10    5                                                       
CONECT   12    9   13   29   34                                             
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14    8   16                                                  
CONECT   16   15                                                            
CONECT   17   13   18   28                                                  
CONECT   18   17   19   22                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   18   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   17   29   30                                                  
CONECT   29   28   12                                                       
CONECT   30   28   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   12                                                            
CONECT   35    9                                                            
CONECT   36    6                                                            
CONECT   37    4                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
11-Keto fuidate	Generator

Chemical Formula

C₃₁H₄₄O₆

Average Mass

512.6870 Da

Monoisotopic Mass

512.31379 Da

IUPAC Name

2-[(1S,2S,6S,7S,10S,11S,13S,14Z,15R)-13-(acetyloxy)-2,6,10,11-tetramethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-ylidene]-6-methylhept-5-enoic acid

Traditional Name

2-[(1S,2S,6S,7S,10S,11S,13S,14Z,15R)-13-(acetyloxy)-2,6,10,11-tetramethyl-5,17-dioxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-ylidene]-6-methylhept-5-enoic acid

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H]2CC[C@@]3(C)[C@@H](C(=O)C[C@H]4\C([C@H](C[C@]34C)OC(C)=O)=C(/CCC=C(C)C)C(O)=O)[C@@]2(C)CCC1=O

InChI Identifier

InChI=1S/C31H44O6/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/h9,18,21-22,25,27H,8,10-16H2,1-7H3,(H,35,36)/b26-20-/t18-,21-,22-,25-,27-,29-,30-,31-/m0/s1

InChI Key

XHWNFPOLQYKPKS-CNZZPSATSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Epidermophyton floccosum 8051	Fungi	KNApSAcK
Fusidium coccineum	-	KNApSAcK

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-oxo-5-alpha-steroid
Oxosteroid
11-oxosteroid
3-oxosteroid
Medium-chain fatty acid
Methyl-branched fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Cyclic ketone
Ketone
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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	4.71	ALOGPS
logP	5.19	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.61	ChemAxon
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	97.74 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	142.27 m³·mol⁻¹	ChemAxon
Polarizability	58.48 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

20100271

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21155584

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 3-Ketofusidic acid (NP0062186)

MOL for NP0062186 (3-Ketofusidic acid)

3D MOL for NP0062186 (3-Ketofusidic acid)

3D SDF for NP0062186 (3-Ketofusidic acid)

3D-SDF for NP0062186 (3-Ketofusidic acid)

PDB for NP0062186 (3-Ketofusidic acid)

3D PDB for NP0062186 (3-Ketofusidic acid)

SMILES for NP0062186 (3-Ketofusidic acid)

INCHI for NP0062186 (3-Ketofusidic acid)

Structure for NP0062186 (3-Ketofusidic acid)

3D Structure for NP0062186 (3-Ketofusidic acid)