NP-MRD: Showing NP-Card for ketoconazol (NP0171505)

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Record Information

Version

2.0

Created at

2022-09-03 08:03:06 UTC

Updated at

2022-09-03 08:03:06 UTC

NP-MRD ID

NP0171505

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ketoconazol

Description

Ketoconazole, also known as nizoral or xolegel, belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group. The less toxic and more effective triazole compounds fluconazole and itraconazole have largely replaced ketoconazole for internal use. The primary mechanism of action is via inhibition of the 11-β-hydroxylase enzyme, the terminal step in cortisol synthesis in the adrenal gland. Ketoconazole is a very strong basic compound (based on its pKa). Ketoconazole is very lipophilic, which leads to accumulation in fatty tissues. Ketoconazole is sold commercially as an anti-dandruff shampoo. Ketoconazole (pronounced /ˌkiːtoʊˈkoʊnəzoʊl/) is a synthetic antifungal drug used to prevent and treat skin and fungal infections, especially in immunocompromised patients such as those with AIDS. Ketoconazole can also inhibit the synthesis of thromboxane and sterols such as aldosterone, cortisol, and testosterone. This results in inhibition of ergosterol synthesis and increased fungal cellular permeability. ketoconazol is found in Streptomyces hygroscopicus. DIO-902 has also been shown to lower total and LDL-cholesterol by inhibiting 14-α-demethylase, a key enzyme in cholesterol synthesis.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241203522D          

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M  END

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M  END


  Mrv0541 02241203522D          

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M  END
> <DATABASE_ID>
NP0171505

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N1CCN(CC1)C1=CC=C(OC[C@@H]2CO[C@](CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m1/s1

> <INCHI_KEY>
XMAYWYJOQHXEEK-ZEQKJWHPSA-N

> <FORMULA>
C26H28Cl2N4O4

> <MOLECULAR_WEIGHT>
531.431

> <EXACT_MASS>
530.148760818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
54.666767639117076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-[4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one

> <ALOGPS_LOGP>
4.30

> <JCHEM_LOGP>
4.191597861333333

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
6.746571393297444

> <JCHEM_POLAR_SURFACE_AREA>
69.06

> <JCHEM_REFRACTIVITY>
138.06719999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.31e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nizoral

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      26.272 -24.358   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.042 -23.025   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      26.272 -21.691   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      27.042 -20.357   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.272 -19.024   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      24.732 -19.024   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      23.962 -20.357   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.732 -21.691   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.962 -17.690   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.732 -16.357   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.962 -15.023   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.422 -15.023   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.652 -16.357   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.422 -17.690   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      21.652 -13.689   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      20.113 -13.689   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.343 -12.356   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      19.969 -10.949   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      18.825  -9.918   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      17.491 -10.688   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.586  -9.443   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      17.212  -8.036   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      18.719  -7.716   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.879  -6.184   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      17.473  -5.558   0.000  0.00  0.00           N+0
HETATM   26  C   UNK     0      16.442  -6.702   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.959 -10.849   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      15.054  -9.603   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.523  -9.764   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      12.897 -11.171   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.801 -12.417   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      15.333 -12.256   0.000  0.00  0.00           C+0
HETATM   33 Cl   UNK     0      16.239 -13.502   0.000  0.00  0.00          Cl+0
HETATM   34 Cl   UNK     0      11.365 -11.332   0.000  0.00  0.00          Cl+0
HETATM   35  O   UNK     0      17.811 -12.195   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      28.582 -23.025   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   36                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    3    7                                                       
CONECT    9    6   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14    9   13                                                       
CONECT   15   12   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   35                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   27   35                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   22   25                                                       
CONECT   27   20   28   32                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   27   31   33                                                  
CONECT   33   32                                                            
CONECT   34   30                                                            
CONECT   35   17   20                                                       
CONECT   36    2                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
(2S,4R)-1-Acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine	ChEBI
1-ACETYL-4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine	ChEBI
Nizoral	Kegg
Xolegel	Kegg
(+-)-cis-1-Acetyl-4-(p-((2-(2,4-dichlorophenyl)-2-(imidazol-1- ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine	HMDB
cis-1-Acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1H- imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-ketoconazol	HMDB
Fungarest	HMDB
Fungoral	HMDB
Ketoderm	HMDB
Ketoisdin	HMDB
Orifungal m	HMDB
Panfungol	HMDB
Piperazine	HMDB
Janssen brand OF ketoconazole	HMDB
Ketoconazole janssen brand	HMDB
Ketoconazole	MeSH

Chemical Formula

C₂₆H₂₈Cl₂N₄O₄

Average Mass

531.4310 Da

Monoisotopic Mass

530.14876 Da

IUPAC Name

1-[4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one

Traditional Name

nizoral

CAS Registry Number

Not Available

SMILES

CC(=O)N1CCN(CC1)C1=CC=C(OC[C@@H]2CO[C@](CN3C=CN=C3)(O2)C2=CC=C(Cl)C=C2Cl)C=C1

InChI Identifier

InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m1/s1

InChI Key

XMAYWYJOQHXEEK-ZEQKJWHPSA-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
Streptomyces hygroscopicus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

Phenylpiperazines

Alternative Parents

Substituents

Phenylpiperazine
N-arylpiperazine
Aminophenyl ether
1,3-dichlorobenzene
Phenol ether
Tertiary aliphatic/aromatic amine
Phenoxy compound
Dialkylarylamine
Aniline or substituted anilines
Alkyl aryl ether
Ketal
Halobenzene
Chlorobenzene
Monocyclic benzene moiety
Aryl chloride
Aryl halide
N-substituted imidazole
Benzenoid
Meta-dioxolane
Heteroaromatic compound
Tertiary carboxylic acid amide
Imidazole
Azole
Acetamide
Carboxamide group
Amino acid or derivatives
Tertiary amine
Acetal
Oxacycle
Azacycle
Carboxylic acid derivative
Ether
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Amine
Organonitrogen compound
Organochloride
Organopnictogen compound
Organohalogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

cis-1-acetyl-4-(4-\{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy\}phenyl)piperazine (CHEBI:47518 )

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	4.3	ALOGPS
logP	4.19	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	6.75	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	138.07 m³·mol⁻¹	ChemAxon
Polarizability	54.67 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon