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Record Information
Version2.0
Created at2022-09-10 21:29:37 UTC
Updated at2022-09-10 21:29:37 UTC
NP-MRD IDNP0305564
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,3-dimethoxy-6-[(2e,5e,7e,9r,10r,11e)-10-methoxy-3,7,9,11-tetramethyltetradeca-2,5,7,11-tetraen-1-yl]-5-methylpyridin-4-ol
DescriptionPiericidin B5 belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 2,3-dimethoxy-6-[(2e,5e,7e,9r,10r,11e)-10-methoxy-3,7,9,11-tetramethyltetradeca-2,5,7,11-tetraen-1-yl]-5-methylpyridin-4-ol was first documented in 1993 (PMID: 8500999). Based on a literature review very few articles have been published on Piericidin B5.
Structure
Thumb
Synonyms
ValueSource
Piericidin b1MeSH
Chemical FormulaC27H41NO4
Average Mass443.6280 Da
Monoisotopic Mass443.30356 Da
IUPAC Name2,3-dimethoxy-6-[(2E,5E,7E,9R,10R,11E)-10-methoxy-3,7,9,11-tetramethyltetradeca-2,5,7,11-tetraen-1-yl]-5-methylpyridin-4-ol
Traditional Name2,3-dimethoxy-6-[(2E,5E,7E,9R,10R,11E)-10-methoxy-3,7,9,11-tetramethyltetradeca-2,5,7,11-tetraen-1-yl]-5-methylpyridin-4-ol
CAS Registry NumberNot Available
SMILES
CC\C=C(/C)[C@H](OC)[C@H](C)\C=C(/C)\C=C\C\C(C)=C\CC1=NC(OC)=C(OC)C(O)=C1C
InChI Identifier
InChI=1S/C27H41NO4/c1-10-12-20(4)25(30-7)21(5)17-19(3)14-11-13-18(2)15-16-23-22(6)24(29)26(31-8)27(28-23)32-9/h11-12,14-15,17,21,25H,10,13,16H2,1-9H3,(H,28,29)/b14-11+,18-15+,19-17+,20-12+/t21-,25+/m1/s1
InChI KeyJWSULLTVTKIFHQ-GSVHENJOSA-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 OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Farsesane sesquiterpenoid
  • Alkyl aryl ether
  • Dihydropyridine
  • Methylpyridine
  • Hydropyridine
  • Pyridine
  • Heteroaromatic compound
  • Vinylogous amide
  • Vinylogous ester
  • Cyclic ketone
  • Azacycle
  • Ether
  • Dialkyl ether
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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
logP6.47ChemAxon
pKa (Strongest Acidic)10.91ChemAxon
pKa (Strongest Basic)1.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area60.81 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity136.64 m³·mol⁻¹ChemAxon
Polarizability51.94 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00016815
Chemspider ID24604035
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44608044
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Nishioka H, Sawa T, Takahashi Y, Naganawa H, Hamada M, Takeuchi T, Umezawa K: Isolation and structure determination of novel phosphatidylinositol turnover inhibitors, piericidin B5 and B5 N-oxide, from Streptomyces sp. J Antibiot (Tokyo). 1993 Apr;46(4):564-8. doi: 10.7164/antibiotics.46.564. [PubMed:8500999 ]
  2. LOTUS database [Link]