Metabolite M4 (Ketoconazole)

Name

M4 (Ketoconazole)

Description

Not Available

Structure

Similar Structures

Synonyms

Not Available

UNII

Not Available

CAS number

Not Available

Weight

Average: 480.39
Monoisotopic: 479.1378618

Chemical Formula

C₂₃H₂₇Cl₂N₃O₄

InChI Key

DXZDAEOUYUGHCZ-UHFFFAOYSA-N

InChI

InChI=1S/C23H27Cl2N3O4/c1-16(29)27-8-10-28(11-9-27)18-3-5-19(6-4-18)30-13-20-14-31-23(15-26,32-20)21-7-2-17(24)12-22(21)25/h2-7,12,20H,8-11,13-15,26H2,1H3

IUPAC Name

1-[4-(4-{[2-(aminomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one

SMILES

CC(=O)N1CCN(CC1)C1=CC=C(OCC2COC(CN)(O2)C2=CC=C(Cl)C=C2Cl)C=C1

Reactions

Ketoconazole

Ketoconazole epoxide intermediate
- Ketoconazole epoxide intermediate
  
  Ketoconazole ketone intermediate
  - Ketoconazole ketone intermediate
    
    Ketoconazole ketone hydroxyl intermediate
    - Ketoconazole ketone hydroxyl intermediate
      
      M2 (Ketoconazole)
    - Ketoconazole ketone hydroxyl intermediate
      
      M5 (Ketoconazole)
- Ketoconazole epoxide intermediate
  
  Ketoconazole dihydroxyl intermediate
  - Ketoconazole dihydroxyl intermediate
    
    M5' (Ketoconazole)
  - Ketoconazole dihydroxyl intermediate
    
    M3 (Ketoconazole)
    - M3 (Ketoconazole)
      
      M4 (Ketoconazole)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-001i-0000900000-878a2a0f170f099ac333
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-004r-0000900000-d75197b870e16ae064fb
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-001i-0023900000-d83b5462cccbcbbe915b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-002r-1042900000-58c728ba6aace2e62cd8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0h3r-0134900000-e6fbac76198d799f1eac
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-00c0-1953200000-968c7f6c2df765834e0d

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	206.09451	predicted	DeepCCS 1.0 (2019)
[M+H]+	208.45253	predicted	DeepCCS 1.0 (2019)
[M+Na]+	215.08113	predicted	DeepCCS 1.0 (2019)

External Links

Not Available

Predicted Properties

Property	Value	Source
logP	3.49	Chemaxon
pKa (Strongest Basic)	8.19	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	1	Chemaxon
Polar Surface Area	77.26 Å²	Chemaxon
Rotatable Bond Count	6	Chemaxon
Refractivity	124.08 m³·mol^-1	Chemaxon
Polarizability	50.32 Å³	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Metabolite M4 (Ketoconazole)

Structure for M4 (Ketoconazole)

Collision Cross Sections (CCS)