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Record Information
Version1.0
Created at2022-09-12 07:47:42 UTC
Updated at2022-09-12 07:47:42 UTC
NP-MRD IDNP0326334
Secondary Accession NumbersNone
Natural Product Identification
Common Name({4-methoxy-1h,1'h-[2,2'-bipyrrol]-5-yl}methylidene)(2-methylpropyl)amine
DescriptionTambjamine C belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl group. ({4-methoxy-1h,1'h-[2,2'-bipyrrol]-5-yl}methylidene)(2-methylpropyl)amine is found in Tambja abdere, Tambja eliora and Virididentula dentata. It was first documented in 2010 (PMID: 20601498). Based on a literature review a significant number of articles have been published on Tambjamine C (PMID: 33371682) (PMID: 29594310) (PMID: 28396364) (PMID: 27384057).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC14H19N3O
Average Mass245.3260 Da
Monoisotopic Mass245.15281 Da
IUPAC Name({4-methoxy-1H,1'H-[2,2'-bipyrrole]-5-yl}methylidene)(2-methylpropyl)amine
Traditional Name({4-methoxy-1H,1'H-[2,2'-bipyrrole]-5-yl}methylidene)(2-methylpropyl)amine
CAS Registry NumberNot Available
SMILES
COC1=C(NC(=C1)C1=CC=CN1)C=NCC(C)C
InChI Identifier
InChI=1S/C14H19N3O/c1-10(2)8-15-9-13-14(18-3)7-12(17-13)11-5-4-6-16-11/h4-7,9-10,16-17H,8H2,1-3H3
InChI KeyHZQMJRAGKHISIU-UHFFFAOYSA-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
Tambja abdereLOTUS Database
Tambja elioraLOTUS Database
Virididentula dentataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkyl aryl ethers. These are organic compounds containing the alkyl aryl ether functional group with the generic formula R-O-R' , where R is an alkyl group and R' is an aryl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentAlkyl aryl ethers
Alternative Parents
Substituents
  • Alkyl aryl ether
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Shiff base
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Aldimine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Imine
  • 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
logP2.58ChemAxon
pKa (Strongest Acidic)14.04ChemAxon
pKa (Strongest Basic)6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.17 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity74.09 m³·mol⁻¹ChemAxon
Polarizability28.73 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound135610509
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Takaki M, Freire VF, Nicacio KJ, Bertonha AF, Nagashima N, Sarpong R, Padula V, Ferreira AG, Berlinck RGS: Metabolomics Reveals Minor Tambjamines in a Marine Invertebrate Food Chain. J Nat Prod. 2021 Mar 26;84(3):790-796. doi: 10.1021/acs.jnatprod.0c01043. Epub 2020 Dec 29. [PubMed:33371682 ]
  2. Marchetti PM, Kelly V, Simpson JP, Ward M, Campopiano DJ: The carbon chain-selective adenylation enzyme TamA: the missing link between fatty acid and pyrrole natural product biosynthesis. Org Biomol Chem. 2018 Apr 18;16(15):2735-2740. doi: 10.1039/c8ob00441b. [PubMed:29594310 ]
  3. Manuel-Manresa P, Korrodi-Gregorio L, Hernando E, Villanueva A, Martinez-Garcia D, Rodilla AM, Ramos R, Fardilha M, Moya J, Quesada R, Soto-Cerrato V, Perez-Tomas R: Novel Indole-based Tambjamine-Analogues Induce Apoptotic Lung Cancer Cell Death through p38 Mitogen-Activated Protein Kinase Activation. Mol Cancer Ther. 2017 Jul;16(7):1224-1235. doi: 10.1158/1535-7163.MCT-16-0752. Epub 2017 Apr 10. [PubMed:28396364 ]
  4. Ballestriero F, Nappi J, Zampi G, Bazzicalupo P, Di Schiavi E, Egan S: Caenorhabditis elegans employs innate and learned aversion in response to bacterial toxic metabolites tambjamine and violacein. Sci Rep. 2016 Jul 7;6:29284. doi: 10.1038/srep29284. [PubMed:27384057 ]
  5. Ballestriero F, Thomas T, Burke C, Egan S, Kjelleberg S: Identification of compounds with bioactivity against the nematode Caenorhabditis elegans by a screen based on the functional genomics of the marine bacterium Pseudoalteromonas tunicata D2. Appl Environ Microbiol. 2010 Sep;76(17):5710-7. doi: 10.1128/AEM.00695-10. Epub 2010 Jul 2. [PubMed:20601498 ]
  6. LOTUS database [Link]