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Record Information
Version2.0
Created at2022-04-28 10:41:28 UTC
Updated at2022-04-28 10:41:29 UTC
NP-MRD IDNP0066435
Secondary Accession NumbersNone
Natural Product Identification
Common NameCurvularin
DescriptionCurvularin belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Curvularin is found in Alternaria cinerariae, Cercospora spp., Curvularia spp., Drechslera rostrata IMI 356287, Drechslera sp., Neopetrosia chaliniformis, Penicillium citreo-viride B, Penicillium citreonigrum, Penicillium gilmanii, Penicillium sp. and Penicillium sumatrense. Curvularin was first documented in 2019 (PMID: 31406682). Based on a literature review a small amount of articles have been published on Curvularin (PMID: 34458061) (PMID: 32843724) (PMID: 32252191) (PMID: 31109256).
Structure
Thumb
Synonyms
ValueSource
10,11-DehydrocurvularinMeSH
Chemical FormulaC16H20O5
Average Mass292.3310 Da
Monoisotopic Mass292.13107 Da
IUPAC Name(4S)-11,13-dihydroxy-4-methyl-2,4,5,6,7,8,9,10-octahydro-1H-3-benzoxacyclododecine-2,10-dione
Traditional Name(4S)-11,13-dihydroxy-4-methyl-4,5,6,7,8,9-hexahydro-1H-3-benzoxacyclododecine-2,10-dione
CAS Registry NumberNot Available
SMILES
C[C@H]1CCCCCC(=O)C2=C(CC(=O)O1)C=C(O)C=C2O
InChI Identifier
InChI=1S/C16H20O5/c1-10-5-3-2-4-6-13(18)16-11(8-15(20)21-10)7-12(17)9-14(16)19/h7,9-10,17,19H,2-6,8H2,1H3/t10-/m0/s1
InChI KeyVDUIGYAPSXCJFC-JTQLQIEISA-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
Alternaria cinerariaeFungi
Cercospora spp.-
Curvularia spp.Fungi
Drechslera rostrata IMI 356287Fungi
Drechslera sp.Fungi
Neopetrosia chaliniformisLOTUS Database
Penicillium citreo-viride BFungi
Penicillium citreonigrumLOTUS Database
Penicillium gilmaniiFungi
Penicillium sp.Fungi
Penicillium sumatrenseFungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Macrolide
  • Aryl ketone
  • Aryl alkyl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Vinylogous acid
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP2.68ALOGPS
logP3.33ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)7.78ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity77.62 m³·mol⁻¹ChemAxon
Polarizability30.23 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 IDC00016018
Chemspider ID106658
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCurvularin
METLIN IDNot Available
PubChem Compound119418
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Wang C, Zaman KHAU, Sarotti AM, Wu X, Zheng SL, Cao S: NF-kappaB inhibitory, antimicrobial and antiproliferative potentials of compounds from Hawaiian fungus Aspergillus polyporicola FS910. 3 Biotech. 2021 Aug;11(8):391. doi: 10.1007/s13205-021-02877-7. Epub 2021 Jul 30. [PubMed:34458061 ]
  2. Liu G, Niu S, Liu L: Alterchromanone A, one new chromanone derivative from the mangrove endophytic fungus Alternaria longipes. J Antibiot (Tokyo). 2021 Feb;74(2):152-155. doi: 10.1038/s41429-020-00364-4. Epub 2020 Aug 25. [PubMed:32843724 ]
  3. Banala RR, Vemuri SK, Ev S, Av GR, Gpv S: The Anti-Inflammatory and Cytoprotective Efficiency of Curvularin, a Fungal Macrolactone against Lipopolysaccharide-Induced Inflammatory Response in Nucleus Pulposus Cells: An In Vitro Study. Asian Spine J. 2021 Apr;15(2):143-154. doi: 10.31616/asj.2019.0285. Epub 2020 Apr 8. [PubMed:32252191 ]
  4. Meena M, Samal S: Alternaria host-specific (HSTs) toxins: An overview of chemical characterization, target sites, regulation and their toxic effects. Toxicol Rep. 2019 Jul 17;6:745-758. doi: 10.1016/j.toxrep.2019.06.021. eCollection 2019. [PubMed:31406682 ]
  5. Misihairabgwi JM, Ishola A, Sulyok M, Krska R: Mycotoxin and cyanogenic glycoside assessment of the traditional leafy vegetables mutete and omboga from Namibia. Food Addit Contam Part B Surveill. 2019 Dec;12(4):245-251. doi: 10.1080/19393210.2019.1616829. Epub 2019 May 20. [PubMed:31109256 ]