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Record Information
Version2.0
Created at2022-09-09 00:11:48 UTC
Updated at2022-09-09 00:11:48 UTC
NP-MRD IDNP0276195
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3z,5e,7e,9e,11r,12s,13z,15e,17e,19e,21e,24s)-3-methoxy-5,11,17,21,24-pentamethyl-1-azacyclotetracosa-1,3,5,7,9,13,15,17,19,21-decaene-2,11,12-triol
DescriptionIncednam belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides. (3z,5e,7e,9e,11r,12s,13z,15e,17e,19e,21e,24s)-3-methoxy-5,11,17,21,24-pentamethyl-1-azacyclotetracosa-1,3,5,7,9,13,15,17,19,21-decaene-2,11,12-triol was first documented in 2010 (PMID: 20939604). Based on a literature review very few articles have been published on Incednam (PMID: 23385133).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC29H39NO4
Average Mass465.6340 Da
Monoisotopic Mass465.28791 Da
IUPAC Name(3Z,5E,7E,9E,11R,12S,13Z,15E,17E,19E,21E,24S)-3-methoxy-5,11,17,21,24-pentamethyl-1-azacyclotetracosa-1,3,5,7,9,13,15,17,19,21-decaene-2,11,12-triol
Traditional Name(3Z,5E,7E,9E,11R,12S,13Z,15E,17E,19E,21E,24S)-3-methoxy-5,11,17,21,24-pentamethyl-1-azacyclotetracosa-1,3,5,7,9,13,15,17,19,21-decaene-2,11,12-triol
CAS Registry NumberNot Available
SMILES
CO\C1=C/C(/C)=C/C=C/C=C/[C@@](C)(O)[C@@H](O)\C=C/C=C/C(/C)=C/C=C/C(/C)=C/C[C@H](C)N=C1O
InChI Identifier
InChI=1S/C29H39NO4/c1-22-13-9-10-17-27(31)29(5,33)20-11-7-8-14-24(3)21-26(34-6)28(32)30-25(4)19-18-23(2)16-12-15-22/h7-18,20-21,25,27,31,33H,19H2,1-6H3,(H,30,32)/b8-7+,13-9+,16-12+,17-10-,20-11+,22-15+,23-18+,24-14+,26-21-/t25-,27-,29+/m0/s1
InChI KeyVTLZZYINHDUOQU-DCKIOERHSA-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 macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolactams
Sub ClassNot Available
Direct ParentMacrolactams
Alternative Parents
Substituents
  • Macrolactam
  • Tertiary alcohol
  • 1,2-diol
  • Carboxamide group
  • Lactam
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic 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
logP4.66ChemAxon
pKa (Strongest Acidic)6.17ChemAxon
pKa (Strongest Basic)3.87ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.28 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity151.57 m³·mol⁻¹ChemAxon
Polarizability54.22 ųChemAxon
Number of Rings1ChemAxon
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 ID78438588
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound49845285
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Takada A, Uda K, Ohtani T, Tsukamoto S, Takahashi D, Toshima K: Improved total synthesis of incednam. J Antibiot (Tokyo). 2013 Mar;66(3):155-9. doi: 10.1038/ja.2013.4. Epub 2013 Feb 6. [PubMed:23385133 ]
  2. Ohtani T, Tsukamoto S, Kanda H, Misawa K, Urakawa Y, Fujimaki T, Imoto M, Takahashi Y, Takahashi D, Toshima K: Total synthesis of incednam, the aglycon of incednine. Org Lett. 2010 Nov 5;12(21):5068-71. doi: 10.1021/ol102400c. [PubMed:20939604 ]
  3. LOTUS database [Link]