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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:36:51 UTC
Update Date2022-03-07 02:52:33 UTC
HMDB IDHMDB0030448
Secondary Accession Numbers
  • HMDB30448
Metabolite Identification
Common NameNarasin
DescriptionNarasin, also known as a 28086A or C 18-205, belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated. Narasin is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563861987
Synonyms
ValueSource
4-MethylsalinomycinHMDB
4-Methylsalinomycin, 9ciHMDB
a 28086aHMDB
Antibiotic a 28086aHMDB
Antibiotic C 7819bHMDB
C 18-205HMDB
C 7819bHMDB
Lilly 79891HMDB
MontebanHMDB
Narasin, ban, inn, usanHMDB
NarasineHMDB
NarasinoHMDB
NarasinumHMDB
NarasulHMDB
Salinomycin, 4-methyl-, (4S)HMDB
2-(6-{6-[2-(5-ethyl-5-hydroxy-6-methyloxan-2-yl)-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5⁷.3⁵]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl}-3,5-dimethyloxan-2-yl)butanoateGenerator
NarasinMeSH
Narasin aMeSH
Narasin monosodium saltMeSH
Chemical FormulaC43H72O11
Average Molecular Weight765.0252
Monoisotopic Molecular Weight764.507463146
IUPAC Name2-(6-{6-[2-(5-ethyl-5-hydroxy-6-methyloxan-2-yl)-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5⁷.3⁵]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl}-3,5-dimethyloxan-2-yl)butanoic acid
Traditional Name2-(6-{6-[2-(5-ethyl-5-hydroxy-6-methyloxan-2-yl)-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5⁷.3⁵]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl}-3,5-dimethyloxan-2-yl)butanoic acid
CAS Registry Number55134-13-9
SMILES
CCC(C1OC(C(C)C(O)C(C)C(=O)C(CC)C2OC3(OC4(CCC(C)(O4)C4CCC(O)(CC)C(C)O4)C(O)C=C3)C(C)CC2C)C(C)CC1C)C(O)=O
InChI Identifier
InChI=1S/C43H72O11/c1-12-30(35(46)27(8)34(45)28(9)36-23(4)21-24(5)37(51-36)31(13-2)39(47)48)38-25(6)22-26(7)42(52-38)18-15-32(44)43(54-42)20-19-40(11,53-43)33-16-17-41(49,14-3)29(10)50-33/h15,18,23-34,36-38,44-45,49H,12-14,16-17,19-22H2,1-11H3,(H,47,48)
InChI KeyVHKXXVVRRDYCIK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpene glycosides. These are diterpenoids in which an isoprene unit is glycosylated.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentDiterpene glycosides
Alternative Parents
Substituents
  • Diterpene glycoside
  • Diterpenoid
  • Fatty alcohol
  • Ketal
  • Branched fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Beta-hydroxy ketone
  • Fatty acyl
  • Pyran
  • Oxane
  • Tetrahydrofuran
  • Tertiary alcohol
  • Secondary alcohol
  • Ketone
  • Acetal
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point198 - 200 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0024 g/LALOGPS
logP4.7ALOGPS
logP7.88ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)4.5ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area161.21 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity204.54 m³·mol⁻¹ChemAxon
Polarizability85.61 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+277.14130932474
DeepCCS[M-H]-275.27530932474
DeepCCS[M-2H]-308.51430932474
DeepCCS[M+Na]+282.74730932474
AllCCS[M+H]+268.932859911
AllCCS[M+H-H2O]+268.132859911
AllCCS[M+NH4]+269.632859911
AllCCS[M+Na]+269.832859911
AllCCS[M-H]-260.532859911
AllCCS[M+Na-2H]-267.532859911
AllCCS[M+HCOO]-275.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NarasinCCC(C1OC(C(C)C(O)C(C)C(=O)C(CC)C2OC3(OC4(CCC(C)(O4)C4CCC(O)(CC)C(C)O4)C(O)C=C3)C(C)CC2C)C(C)CC1C)C(O)=O4387.5Standard polar33892256
NarasinCCC(C1OC(C(C)C(O)C(C)C(=O)C(CC)C2OC3(OC4(CCC(C)(O4)C4CCC(O)(CC)C(C)O4)C(O)C=C3)C(C)CC2C)C(C)CC1C)C(O)=O4216.8Standard non polar33892256
NarasinCCC(C1OC(C(C)C(O)C(C)C(=O)C(CC)C2OC3(OC4(CCC(C)(O4)C4CCC(O)(CC)C(C)O4)C(O)C=C3)C(C)CC2C)C(C)CC1C)C(O)=O4601.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Narasin GC-MS (Non-derivatized) - 70eV, Positivesplash10-01r7-8922502300-1e5e71ea627aeb40a30e2017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Narasin GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Narasin GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Narasin GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Narasin GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Narasin GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Narasin GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Narasin GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Narasin GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Narasin GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Narasin GC-MS (TBDMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Narasin GC-MS (TBDMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Narasin GC-MS (TBDMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narasin 10V, Positive-QTOFsplash10-0002-0114301900-9377e2f146585adf5c302017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narasin 20V, Positive-QTOFsplash10-052n-0936301300-2e19decb34456b6c6c7d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narasin 40V, Positive-QTOFsplash10-0q33-3931212000-a171da32e28503ee19312017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narasin 10V, Negative-QTOFsplash10-0401-0152530900-766794181e77bb743eb72017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narasin 20V, Negative-QTOFsplash10-003r-1190000100-4f1fceb15eb6fd28131f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narasin 40V, Negative-QTOFsplash10-05o0-8952421100-5b88b271ac5c732bd62a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narasin 10V, Positive-QTOFsplash10-00mk-0000001900-125c5cdc106800ba44822021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narasin 20V, Positive-QTOFsplash10-01t9-0402704900-fd6aa50ead4f84cb1de52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narasin 40V, Positive-QTOFsplash10-062i-9644148100-dfb3bfbf110e81bc1ac72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narasin 10V, Negative-QTOFsplash10-03di-0000000900-6de0b94819091c45454f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narasin 20V, Negative-QTOFsplash10-03xr-1100174900-181c195ce799d58bba862021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Narasin 40V, Negative-QTOFsplash10-0002-9421150200-b32e14e49aaa0cf1a10f2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB002313
KNApSAcK IDNot Available
Chemspider ID3471627
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNarasin
METLIN IDNot Available
PubChem Compound4264204
PDB IDNot Available
ChEBI ID852738
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.