Natural Product (NP) Details

General Information of the NP (ID: NP1003)
Name
Apalcillin
Synonyms
Apalcillin; apalcilina; 63469-19-2; Apalcilline; Apalcillinum; UNII-3373RT9U7A; C25H23N5O6S; CHEBI:51691; 3373RT9U7A; PC-904; (2S,5R,6R)-6-{[(2R)-2-{[(4-hydroxy-1,5-naphthyridin-3-yl)carbonyl]amino}-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 6beta-{(2R)-2-[(4-hydroxy-1,5-naphthyridin-3-yl)carboxamido]-2-phenylacetamido}-2,2-dimethylpenam-3alpha-carboxylic acid; Apalcillin [INN]; Apalcilina [INN-Spanish]; Apalcilline [INN-French]; Apalcillinum [INN-Latin]; BRN 6030446; SCHEMBL33854; CHEMBL3306902; GTPL10759; DTXSID601016509; PC904; ZINC59817121; (6R)-6-((R)-2-(4-Hydroxy-1,5-naphthyridin-3-carboxamido)-2-phenylacetamido)penicillansaeure; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[[(2R)-2-[(4-oxo-1H-1,5-naphthyridine-3-carbonyl)amino]-2-phenylacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-((R)-2-(4-Hydroxy-1,5-naphthyridin-3-carboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-5-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure; (2S,5R,6R)-6-((R)-2-(4-Hydroxy-1,5-naphthyridin-3-carboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-5-thia-1-azabicyclo(3.2.0)heptan-2-carboxylic acid; U326; WY-44417; WY-44,417; Q15633259; DIETHYL5,5-METHYLENEBIS(4-ETHYL-3-METHYL-2-PYRROLECARBOXYLATE); (2S,5R,6R)-6-(2-(4-hydroxy-1,5-naphthyridine-3-carboxamido)-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2R)-(((4-hydroxy-1,5-naphthyridin-3-yl)carbonyl)amino)phenylacetyl)amino)-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
    Click to Show/Hide
Species Origin Escherichia coli ...     Click to Show/Hide
Escherichia coli
SuperKingdom: Bacteria
Phylum: Proteobacteria
Class: Gammaproteobacteria
Order: Enterobacterales
Family: Enterobacteriaceae
Genus: Escherichia
Species: Escherichia coli
Dauricine (Menispermum dauricum)
SuperKingdom: Eukaryota
Kingdom: Plantae
Phylum: Tracheophyta
Class: Magnoliopsida
Order: Ranunculales
Family: Menispermaceae
Genus: Menispermum
Species: M. dauricum
Disease Fungal infection [ICD-11: 1F29-1F2F] Phase 2 [1]
Gliomas of brain [ICD-11: 2A00.00] Investigative
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -5.828
 
MDCK Permeability
 -5.137
 
PAMPA
 +++
 
HIA
 ++
 
Distribution
VDss
 -0.688
 
PPB
 72%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 +++
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 - -
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 - - -
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 - - -
HLM Stability
 +++
 
Excretion
CLplasma
 1.663
 
T1/2
 1.187
Toxicity
DILI
 +++
 
Rat Oral Acute Toxicity
 - - -
 
FDAMDD
 - - -
 
Respiratory
 - - -
 
Human Hepatotoxicity
 ++
 
Ototoxicity
 -
 
Drug-induced Nephrotoxicity
 +++
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 +
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
    Click to Show/Hide
    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C25H23N5O6S
PubChem CID
6602341
Canonical SMILES
CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)NC(=O)C4=CNC5=C(C4=O)N=CC=C5)C(=O)O)C
InChI
1S/C25H23N5O6S/c1-25(2)19(24(35)36)30-22(34)17(23(30)37-25)29-21(33)15(12-7-4-3-5-8-12)28-20(32)13-11-27-14-9-6-10-26-16(14)18(13)31/h3-11,15,17,19,23H,1-2H3,(H,27,31)(H,28,32)(H,29,33)(H,35,36)/t15-,17-,19+,23-/m1/s1
InChIKey
XMQVYNAURODYCQ-SLFBBCNNSA-N
CAS Number
CAS 63469-19-2
ChEBI ID
CHEBI:51691
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Gentamicin      Bacterial infection     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model For a xenograft model, mice were made neutropenic by intraperitoneal (ip) injection of cyclophosphamide at a dose of 100 mg/kg on days 0, 2,4.
                    Experimental
                    Result(s)		 Apalcillin when combined with gentamicin is effective in treating serious P. aeruginosa bacteraemia in neutropenic mice.
References
Reference 1 ClinicalTrials.gov (NCT00292071) Open, Pharmacokinetic Study of Caspofungin Acetate in Immunocompromised Young Children With Febrile Neutropenia (0991-042)
Reference 2 Synergistic activity of apalcillin and gentamicin in a combination therapy in experimental Pseudomonas bacteraemia of neutropenic mice. J Antimicrob Chemother. 1986 Apr;17(4):499-503.
 Download Picture         KEGG Link