Details of Natural Product (NP)

General Information of Natural Product (ID: NP1636)
  Natural Product Name
Xolegel
  Synonyms
ketoconazole; 65277-42-1; (+)-Ketoconazole; Xolegel; Extina; (2R,4S)-ketoconazole; Kuric; 142128-59-4; Ketocanazole; CPD000058460; CHEMBL75; MFCD00058579; C26H28Cl2N4O4; SMR000058460; MLS000069784; MLS001146934; 1-acetyl-4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine; CHEBI:48336; 1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone; DSSTox_CID_9879; R-41400; DSSTox_RID_78829; DSSTox_GSID_29879; 1-(4-(4-(((2R,4S)-2-((1H-IMIDAZOL-1-YL)METHYL)-2-(2,4-DICHLOROPHENYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)PIPERAZIN-1-YL)ETHANONE; rac-trans-Ketoconazole; KTZ; SR-01000075626; SR-01000597381; Ketoconazole (k); (+)-Ketoconazol; Ketoconazole,(S); NCGC00016907-01; Prestwick_744; CAS-65277-42-1; Tocris-1103; Opera_ID_397; Prestwick0_000389; Prestwick1_000389; Prestwick2_000389; Prestwick3_000389; R 41,400; UPCMLD-DP138; SCHEMBL8407; Lopac0_000666; BSPBio_000577; MLS000758224; MLS001423987; MLS002207053; MLS002222255; BIDD:GT0696; US9150527, Ketoconazole; SPBio_002498; AMY917; BDBM8610; BPBio1_000635; DTXSID7029879; UPCMLD-DP138:001; BDBM60666; HY-B0105A; Ketoconazole, >=98% (HPLC); HMS1569M19; HMS2051A19; HMS2089N05; HMS2096M19; HMS2234H17; HMS3262E13; HMS3414J19; HMS3678J17; HMS3713M19; ZINC643138; BCP28528; Piperazine, (+/-)-1-acetyl-4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-, rel-; Ketoconazole 2.0 mg/ml in Methanol; Tox21_110676; Tox21_300267; Tox21_500666; EI-107; s1353; AKOS007930650; CCG-100815; CS-1846; KS-1205; LP00666; MCULE-2726394491; NC00065; SDCCGSBI-0050645.P002; MRF-0000100; 24F2-1,25(OH)D3; NCGC00025000-01; NCGC00025000-02; NCGC00025000-03; NCGC00025000-04; NCGC00025000-05; NCGC00025000-06; NCGC00025000-07; NCGC00025000-08; NCGC00025000-09; NCGC00025000-10; NCGC00025000-14; NCGC00025000-16; NCGC00025000-28; NCGC00253967-01; NCGC00261351-01; ( inverted exclamation markA)-Ketoconazol; (+/-)-cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine; AC-15957; cis-1-Acetyl-4-[4-[[2-(2,4-; Ketoconazole 100 microg/mL in Acetonitrile; EU-0100666; K0045; SW196888-4; BIM-0050645.0001; J10202; K 1003; 277K421; Ketoconazole, Antibiotic for Culture Media Use Only; Q-201267; SR-01000075626-1; SR-01000075626-4; SR-01000597381-1; SR-01000597381-6; BRD-K29113274-001-03-6; BRD-K29113274-001-11-9; BRD-K29113274-001-21-8; Q27121163; (+)-R 41400; Ketoconazole, British Pharmacopoeia (BP) Reference Standard; UNII-R9400W927I component XMAYWYJOQHXEEK-OZXSUGGESA-N; Ketoconazole, European Pharmacopoeia (EP) Reference Standard; Ketoconazole, United States Pharmacopeia (USP) Reference Standard; dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-piperazine; Ketoconazole, Pharmaceutical Secondary Standard; Certified Reference Material; (+/-)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine; (2R,4S)-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine; 1-(4-(4-(((2R,4S)-2-((1H-imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)ethan-1-one; cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl] methoxy]phenyl]piperazine; KZ; Piperazine, (+)-1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-
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  Formula C26H28Cl2N4O4
  Weight 531.4
  Structure Could Not Find 2D Structure
3D Structure Download 2D Structure Download
  InChI 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-/m0/s1
  InChI Key XMAYWYJOQHXEEK-OZXSUGGESA-N
  Isomeric SMILES CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OC[C@H]3CO[C@](O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
  Canonical SMILES CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
  External Links PubChem ID 456201
CAS ID 65277-42-1
CHEMBL ID CHEMBL75
  NP Activity Charts   Click to show/hide
  Activity Info  

 The Content Variation of Natural Product Induced by Different Factor(s)
      Species Name: Aspergillus clavatonanicus strain MJ31
  Factor Name: PDB medium [1]
              Species Info Factor Info
               Experiment Detail
Healthy plant (Mirabilis jalapa L.) was collected from Dampa Tiger Reserve Forest [DTRF] (23° 44′ N 92° 39′ E), Mizoram, Northeast India during February, 2014. The cut ends were sealed with wax and were brought to the laboratory. Five mycelial agar plug of grown strain was inoculated in 2 L Erlenmeyer flasks containing 700 ml potato dextrose broth (PDB) media and incubated at 26 ℃ for three weeks.
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               Mechanism
Ketosynthase (KS) domain of polyketide synthases (PKS) type I and adenylation (A) domain of non-ribosomal peptide synthetases (NRPS) were detected in strain MJ31 which might play a role in antimicrobial activity. An expected 700 bp band of KS domain was detected by LC3 and LC5C primers which were responsible for the synthesis of partially reducing (PR) type PKSs. NRPS gene was also detected with the amplified product size of 300 bp.
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               Factor Part Location NP Content
 
PDB medium (26℃ + 21 days)
 Root tissues Mizoram, India
NP Content: 63.67 µg/g
References
1 Determination and production of antimicrobial compounds by Aspergillus clavatonanicus strain MJ31, an endophytic fungus from Mirabilis jalapa L. using UPLC-ESI-MS/MS and TD-GC-MS analysis