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Record Information
Version1.0
Created at2022-09-05 21:45:01 UTC
Updated at2022-09-05 21:45:01 UTC
NP-MRD IDNP0220441
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5r,6r)-6-ethyl-3-({2-[(1-hydroxyethylidene)amino]ethyl}sulfanyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
DescriptionPS-5, also known as antibiotic PS 5, belongs to the class of organic compounds known as carbapenems. These are beta-lactam derivatives in which the beta-lactam ring shares the nitrogen atom with a pyrrole-2-carboxylic acid. (5r,6r)-6-ethyl-3-({2-[(1-hydroxyethylidene)amino]ethyl}sulfanyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid is found in Apis cerana. It was first documented in 2021 (PMID: 35480178). Based on a literature review a significant number of articles have been published on PS-5 (PMID: 35978752) (PMID: 35956084) (PMID: 35472354) (PMID: 34688764).
Structure
Thumb
Synonyms
ValueSource
Antibiotic PS 5Kegg
PS 5MeSH
PS 5, Sodium salt, (5R-cis)-isomerMeSH
3-(2-Acetamidoethyl)thio-6-ethyl-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acidMeSH
Chemical FormulaC13H18N2O4S
Average Mass298.3600 Da
Monoisotopic Mass298.09873 Da
IUPAC Name(5R,6R)-6-ethyl-3-({2-[(1-hydroxyethylidene)amino]ethyl}sulfanyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
Traditional Name(5R,6R)-6-ethyl-3-({2-[(1-hydroxyethylidene)amino]ethyl}sulfanyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC[C@@H]1[C@H]2CC(SCCN=C(C)O)=C(N2C1=O)C(O)=O
InChI Identifier
InChI=1S/C13H18N2O4S/c1-3-8-9-6-10(20-5-4-14-7(2)16)11(13(18)19)15(9)12(8)17/h8-9H,3-6H2,1-2H3,(H,14,16)(H,18,19)/t8-,9-/m1/s1
InChI KeyMHSNTZYKSLYGOM-RKDXNWHRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apis ceranaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as carbapenems. These are beta-lactam derivatives in which the beta-lactam ring shares the nitrogen atom with a pyrrole-2-carboxylic acid.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCarbapenems
Alternative Parents
Substituents
  • Carbapenem
  • Alpha-amino acid or derivatives
  • Pyrroline carboxylic acid
  • Pyrroline carboxylic acid or derivatives
  • Azepine
  • Vinylogous thioester
  • Acetamide
  • Tertiary carboxylic acid amide
  • Pyrroline
  • Thioenolether
  • Secondary carboxylic acid amide
  • Azetidine
  • Carboxamide group
  • Azacycle
  • Sulfenyl compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.2ChemAxon
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)6.22ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area90.2 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity77.08 m³·mol⁻¹ChemAxon
Polarizability31.51 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID170200
KEGG Compound IDC17370
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPlayStation 5
METLIN IDNot Available
PubChem Compound196445
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Turnbull ZA, Tangel VE, Goldstein PA: Predictive Value of Emergency Designation on Outcomes of Moribund Patients. Cureus. 2022 Jul 15;14(7):e26875. doi: 10.7759/cureus.26875. eCollection 2022 Jul. [PubMed:35978752 ]
  2. Gonzalez Marcos E, Gonzalez Garcia E, Gonzalez-Santos J, Gonzalez-Bernal JJ, Del Pilar Martin-Rodriguez A, Santamaria-Pelaez M: Determinants of Lack of Recovery from Dependency and Walking Ability Six Months after Hip Fracture in a Population of People Aged 65 Years and Over. J Clin Med. 2022 Jul 31;11(15):4467. doi: 10.3390/jcm11154467. [PubMed:35956084 ]
  3. Dastbaz Z, Dana SN, Ashrafizadeh SN: Preparation of a stabilized aqueous polystyrene suspension via phase inversion. RSC Adv. 2021 May 13;11(29):17547-17557. doi: 10.1039/d1ra02292j. eCollection 2021 May 13. [PubMed:35480178 ]
  4. Jong MC, Li J, Noor HM, He Y, Gin KY: Impacts of size-fractionation on toxicity of marine microplastics: Enhanced integrated biomarker assessment in the tropical mussels, Perna viridis. Sci Total Environ. 2022 Aug 20;835:155459. doi: 10.1016/j.scitotenv.2022.155459. Epub 2022 Apr 23. [PubMed:35472354 ]
  5. Li W, Pan Z, Xu J, Liu Q, Zou Q, Lin H, Wu L, Huang H: Microplastics in a pelagic dolphinfish (Coryphaena hippurus) from the Eastern Pacific Ocean and the implications for fish health. Sci Total Environ. 2022 Feb 25;809:151126. doi: 10.1016/j.scitotenv.2021.151126. Epub 2021 Oct 22. [PubMed:34688764 ]
  6. LOTUS database [Link]