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Record Information
Version2.0
Created at2020-12-09 05:43:56 UTC
Updated at2021-07-15 16:59:25 UTC
NP-MRD IDNP0008099
Secondary Accession NumbersNone
Natural Product Identification
Common NameArthrinic acid
Provided ByNPAtlasNPAtlas Logo
Description(6E,10E,14E,18E,20E)-2,3,5,9,13,17-hexahydroxy-20-(hydroxymethyl)-14,16,18,22,24-pentamethylhexacosa-6,10,14,18,20-pentaenoic acid belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Arthrinic acid is found in Arthrinium phaeospermum. Arthrinic acid was first documented in 2008 (PMID: 18997391). Based on a literature review very few articles have been published on (6E,10E,14E,18E,20E)-2,3,5,9,13,17-hexahydroxy-20-(hydroxymethyl)-14,16,18,22,24-pentamethylhexacosa-6,10,14,18,20-pentaenoic acid (PMID: 31642712).
Structure
Thumb
Synonyms
ValueSource
(6E,10E,14E,18E,20E)-2,3,5,9,13,17-Hexahydroxy-20-(hydroxymethyl)-14,16,18,22,24-pentamethylhexacosa-6,10,14,18,20-pentaenoateGenerator
ArthrinateGenerator
Chemical FormulaC32H54O9
Average Mass582.7750 Da
Monoisotopic Mass582.37678 Da
IUPAC Name(2R,3S,5S,6E,9R,10E,13S,14E,16S,17S,18E,20E,22R,24R)-2,3,5,9,13,17-hexahydroxy-20-(hydroxymethyl)-14,16,18,22,24-pentamethylhexacosa-6,10,14,18,20-pentaenoic acid
Traditional Name(2R,3S,5S,6E,9R,10E,13S,14E,16S,17S,18E,20E,22R,24R)-2,3,5,9,13,17-hexahydroxy-20-(hydroxymethyl)-14,16,18,22,24-pentamethylhexacosa-6,10,14,18,20-pentaenoic acid
CAS Registry NumberNot Available
SMILES
CCC(C)CC(C)\C=C(\CO)/C=C(\C)C(O)C(C)\C=C(/C)C(O)C\C=C\C(O)C\C=C\C(O)CC(O)C(O)C(O)=O
InChI Identifier
InChI=1S/C32H54O9/c1-7-20(2)14-21(3)15-25(19-33)17-24(6)30(38)23(5)16-22(4)28(36)13-9-11-26(34)10-8-12-27(35)18-29(37)31(39)32(40)41/h8-9,11-12,15-17,20-21,23,26-31,33-39H,7,10,13-14,18-19H2,1-6H3,(H,40,41)/b11-9+,12-8+,22-16+,24-17+,25-15+
InChI KeyVTIWIBQZTPEOSH-ZQZRMASVSA-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
Arthrinium phaeospermumNPAtlas
Chemical Taxonomy
Description Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative Parents
Substituents
  • Very long-chain fatty acid
  • Acyclic diterpenoid
  • Diterpenoid
  • Beta-hydroxy acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Alpha-hydroxy acid
  • Monosaccharide
  • Hydroxy acid
  • Secondary alcohol
  • 1,2-diol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Carbonyl group
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Primary alcohol
  • Organic oxide
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP2.57ALOGPS
logP2.34ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)3.63ChemAxon
pKa (Strongest Basic)-0.86ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area178.91 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity165.74 m³·mol⁻¹ChemAxon
Polarizability66.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA007685
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28285642
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25105203
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Bloor S: Arthrinic acid, a novel antifungal polyhydroxyacid from Arthrinium phaeospermum. J Antibiot (Tokyo). 2008 Aug;61(8):515-7. doi: 10.1038/ja.2008.69. [PubMed:18997391 ]
  2. Zhao Z, Ding W, Wang PM, Zheng D, Xu J: Five polyketides isolated from the marine-derived fungus Arthrinium Sp. Nat Prod Res. 2021 Aug;35(15):2470-2475. doi: 10.1080/14786419.2019.1680663. Epub 2019 Oct 23. [PubMed:31642712 ]