Np mrd loader

Record Information
Version1.0
Created at2021-06-19 17:41:50 UTC
Updated at2021-06-29 23:50:40 UTC
NP-MRD IDNP0025615
Secondary Accession NumbersNone
Natural Product Identification
Common NameFumagillin
Provided ByJEOL DatabaseJEOL Logo
DescriptionFumagillin is also known as fumidil b. Fumagillin is found in Aspergillus fumigatus and Penicillium janczewskii. It was first documented in 2021 (PMID: 33932203). Based on a literature review a significant number of articles have been published on fumagillin (PMID: 33924845) (PMID: 33903300) (PMID: 33846894) (PMID: 33806001).
Structure
Thumb
Synonyms
ValueSource
Fumidil bMeSH
Chemical FormulaC26H34O7
Average Mass458.5510 Da
Monoisotopic Mass458.23045 Da
IUPAC Name(2E,4E,6E,8E)-10-{[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3S)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid
Traditional Name(2E,4E,6E,8E)-10-{[(3R,4S,5S,6R)-5-methoxy-4-[(2R,3S)-2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-1-oxaspiro[2.5]octan-6-yl]oxy}-10-oxodeca-2,4,6,8-tetraenoic acid
CAS Registry NumberNot Available
SMILES
[H]OC(=O)C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])\C(\[H])=C(/[H])C(=O)O[C@]1([H])C([H])([H])C([H])([H])[C@@]2(OC2([H])[H])[C@]([H])([C@]1([H])OC([H])([H])[H])[C@]1(O[C@@]1([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C26H34O7/c1-18(2)13-14-20-25(3,33-20)24-23(30-4)19(15-16-26(24)17-31-26)32-22(29)12-10-8-6-5-7-9-11-21(27)28/h5-13,19-20,23-24H,14-17H2,1-4H3,(H,27,28)/b7-5+,8-6+,11-9+,12-10+/t19-,20+,23-,24-,25+,26+/m1/s1
InChI KeyNGGMYCMLYOUNGM-AFISTTPQSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aspergillus fumigatusJEOL database
    • Chu, M., et al, J. Antibiotics 54, 1096 (2001)
Penicillium janczewskiiFungi
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Branched fatty acid
  • Epoxy fatty acid
  • Fatty acid ester
  • Heterocyclic fatty acid
  • Dicarboxylic acid or derivatives
  • Unsaturated fatty acid
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP4.61ALOGPS
logP4.05ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)4.88ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area97.89 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity128.37 m³·mol⁻¹ChemAxon
Polarizability50.83 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID23256713
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkFumagillin
METLIN IDNot Available
PubChem Compound40473210
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Ben Abdelkader F, Cakmak I, Cakmak SS, Nur Z, Incebiyik E, Aktar A, Erdost H: Toxicity assessment of chronic exposure to common insecticides and bee medications on colony development and drones sperm parameters. Ecotoxicology. 2021 Jul;30(5):806-817. doi: 10.1007/s10646-021-02416-3. Epub 2021 May 1. [PubMed:33932203 ]
  2. Nanetti A, Ugolini L, Cilia G, Pagnotta E, Malaguti L, Cardaio I, Matteo R, Lazzeri L: Seed Meals from Brassica nigra and Eruca sativa Control Artificial Nosema ceranae Infections in Apis mellifera. Microorganisms. 2021 Apr 28;9(5). pii: microorganisms9050949. doi: 10.3390/microorganisms9050949. [PubMed:33924845 ]
  3. Mohamed Yusoff PS, Osman E, Raja Sabudin RZA: Disseminated microsporidiosis: An underdiagnosed and emerging opportunistic disease. Malays J Pathol. 2021 Apr;43(1):9-18. [PubMed:33903300 ]
  4. Albayati S, Uba AI, Yelekci K: Potential inhibitors of methionine aminopeptidase type II identified via structure-based pharmacophore modeling. Mol Divers. 2021 Apr 13. pii: 10.1007/s11030-021-10221-7. doi: 10.1007/s11030-021-10221-7. [PubMed:33846894 ]
  5. Glavinic U, Stevanovic J, Ristanic M, Rajkovic M, Davitkov D, Lakic N, Stanimirovic Z: Potential of Fumagillin and Agaricus blazei Mushroom Extract to Reduce Nosema ceranae in Honey Bees. Insects. 2021 Mar 25;12(4). pii: insects12040282. doi: 10.3390/insects12040282. [PubMed:33806001 ]
  6. Chu, M., et al. (2001). Chu, M., et al, J. Antibiotics 54, 1096 (2001). J. Antibiotics.