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Record Information
Version1.0
Created at2020-09-23 01:57:32 UTC
Updated at2021-08-10 02:55:27 UTC
NP-MRD IDNP0001585
Secondary Accession NumbersNone
Natural Product Identification
Common NameTumonic acid A
Provided ByNPAtlasNPAtlas Logo
Description(2S)-1-[(2R,4E)-3-hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carboxylic acid belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Tumonic acid A is found in Lyngbya majuscula. It was first documented in 1999 (PMID: 10096859). Based on a literature review very few articles have been published on (2S)-1-[(2R,4E)-3-hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carboxylic acid.
Structure
Data?1628564127
Synonyms
ValueSource
(2S)-1-[(2R,4E)-3-Hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carboxylateGenerator
Tumonate aGenerator
Chemical FormulaC19H33NO4
Average Mass339.4760 Da
Monoisotopic Mass339.24096 Da
IUPAC Name(2S)-1-[(2R,3S,4E)-3-hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carboxylic acid
Traditional Nametumonoic acid A
CAS Registry NumberNot Available
SMILES
[H]OC(=O)[C@@]1([H])N(C(=O)[C@]([H])(C([H])([H])[H])[C@]([H])(O[H])C(=C(/[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])\C([H])([H])[H])C([H])([H])C([H])([H])C1([H])[H]
InChI Identifier
InChI=1S/C19H33NO4/c1-4-5-6-7-8-9-11-14(2)17(21)15(3)18(22)20-13-10-12-16(20)19(23)24/h11,15-17,21H,4-10,12-13H2,1-3H3,(H,23,24)/b14-11+/t15-,16+,17-/m1/s1
InChI KeyJFFANXXIOVCBBG-ZSVBRUDFSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Lyngbya majuscula
Chemical Taxonomy
Description Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentProline and derivatives
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Proline or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid
  • Pyrrolidine carboxylic acid or derivatives
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Carboxamide group
  • Secondary alcohol
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Carbonyl group
  • Alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • 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
logP10(3.36) g/LALOGPS
logP10(3.56) g/LChemAxon
logS10(-3.2) g/LALOGPS
pKa (Strongest Acidic)3.99ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area77.84 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity95 m³·mol⁻¹ChemAxon
Polarizability39.34 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA016368
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10477627
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21775356
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Harrigan GG, Luesch H, Yoshida WY, Moore RE, Nagle DG, Biggs J, Park PU, Paul VJ: Tumonoic acids, novel metabolites from a cyanobacterial assemblage of Lyngbya majuscula and Schizothrix calcicola. J Nat Prod. 1999 Mar;62(3):464-7. doi: 10.1021/np980460u. [PubMed:10096859 ]