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Record Information
Version1.0
Created at2020-09-23 01:57:36 UTC
Updated at2021-08-10 02:55:28 UTC
NP-MRD IDNP0001587
Secondary Accession NumbersNone
Natural Product Identification
Common NameTumonic acid C
Provided ByNPAtlasNPAtlas Logo
Description(2S)-2-{[(2R)-2-[(2S)-1-[(2R,4E)-3-hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carbonyloxy]-3-methylbutanoyl]oxy}propanoic acid belongs to the class of organic compounds known as depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids), commonly but not necessarily regularly alternating. Tumonic acid C 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)-2-{[(2R)-2-[(2S)-1-[(2R,4E)-3-hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carbonyloxy]-3-methylbutanoyl]oxy}propanoic acid.
Structure
Data?1628564128
Synonyms
ValueSource
(2S)-2-{[(2R)-2-[(2S)-1-[(2R,4E)-3-hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carbonyloxy]-3-methylbutanoyl]oxy}propanoateGenerator
Tumonate CGenerator
Chemical FormulaC27H45NO8
Average Mass511.6560 Da
Monoisotopic Mass511.31452 Da
IUPAC Name(2S)-2-{[(2R)-2-[(2S)-1-[(2R,3S,4E)-3-hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carbonyloxy]-3-methylbutanoyl]oxy}propanoic acid
Traditional Name(2S)-2-{[(2R)-2-[(2S)-1-[(2R,3S,4E)-3-hydroxy-2,4-dimethyldodec-4-enoyl]pyrrolidine-2-carbonyloxy]-3-methylbutanoyl]oxy}propanoic acid
CAS Registry NumberNot Available
SMILES
[H]OC(=O)[C@@]([H])(OC(=O)[C@]([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])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C27H45NO8/c1-7-8-9-10-11-12-14-18(4)22(29)19(5)24(30)28-16-13-15-21(28)26(33)36-23(17(2)3)27(34)35-20(6)25(31)32/h14,17,19-23,29H,7-13,15-16H2,1-6H3,(H,31,32)/b18-14+/t19-,20+,21+,22-,23-/m1/s1
InChI KeyJMMSUMNUHPWPOM-OTXNQVFESA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lyngbya majusculaNPAtlas
Chemical Taxonomy
Description Belongs to the class of organic compounds known as depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids), commonly but not necessarily regularly alternating.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassDepsipeptides
Direct ParentDepsipeptides
Alternative Parents
Substituents
  • Depsipeptide
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Alpha-amino acid ester
  • Proline or derivatives
  • Alpha-amino acid or derivatives
  • Tricarboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Fatty acid ester
  • Fatty acyl
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organopnictogen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • 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
logP4.21ALOGPS
logP4.84ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.54ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area130.44 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity134.69 m³·mol⁻¹ChemAxon
Polarizability56.84 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA002096
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10477630
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound21775359
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 ]