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Record Information
Version2.0
Created at2021-01-06 07:01:19 UTC
Updated at2021-07-15 17:37:10 UTC
NP-MRD IDNP0021749
Secondary Accession NumbersNone
Natural Product Identification
Common NamePentalenolactone
Provided ByNPAtlasNPAtlas Logo
DescriptionPentalenolactone is also known as arenaemycin e or PA-132. Pentalenolactone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Pentalenolactone is found in Streptomyces filipinensis and Unknown-fungus sp.. Pentalenolactone was first documented in 1969 (PMID: 5808206). Based on a literature review a small amount of articles have been published on Pentalenolactone (PMID: 11137857) (PMID: 11440152).
Structure
Data?1624506926
Synonyms
ValueSource
Arenaemycin eChEBI
ArenemycineChEBI
PA-132ChEBI
Chemical FormulaC15H16O5
Average Mass276.2880 Da
Monoisotopic Mass276.09977 Da
IUPAC Name(1'S,2R,4'S,5'R,8'R)-3',4'-dimethyl-11'-oxo-10'-oxaspiro[oxirane-2,12'-tricyclo[6.4.0.0^{1,5}]dodecane]-2',6'-diene-7'-carboxylic acid
Traditional Name(1'S,2R,4'S,5'R,8'R)-3',4'-dimethyl-11'-oxo-10'-oxaspiro[oxirane-2,12'-tricyclo[6.4.0.0^{1,5}]dodecane]-2',6'-diene-7'-carboxylic acid
CAS Registry NumberNot Available
SMILES
C[C@H]1[C@H]2C=C([C@@H]3COC(=O)[C@]4(CO4)[C@]23C=C1C)C(O)=O
InChI Identifier
InChI=1S/C15H16O5/c1-7-4-14-10(8(7)2)3-9(12(16)17)11(14)5-19-13(18)15(14)6-20-15/h3-4,8,10-11H,5-6H2,1-2H3,(H,16,17)/t8-,10-,11+,14-,15-/m1/s1
InChI KeyNUPNVWUYFVEAIT-UJJBCWTCSA-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
Streptomyces filipinensisLOTUS Database
Unknown-fungus sp.NPAtlas
Species Where Detected
Species NameSourceReference
Streptomyces sp. AA-57 spp.KNApSAcK Database
Chemical Taxonomy
ClassificationNot classified
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
logP1.81ALOGPS
logP0.87ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)4.23ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.13 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity69.7 m³·mol⁻¹ChemAxon
Polarizability27.18 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA014531
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00021801
Chemspider ID28533317
KEGG Compound IDC20407
BioCyc IDCPD-13619
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24199350
PDB IDNot Available
ChEBI ID70816
Good Scents IDNot Available
References
General References
  1. Takeuchi S, Ogawa Y, Yonehara H: The structure of pentalenolactone (PA-132). Tetrahedron Lett. 1969 Jul;(32):2737-40. doi: 10.1016/s0040-4039(01)88256-3. [PubMed:5808206 ]
  2. Ikeda M, Fukuda A, Takagi M, Morita M, Shimada Y: Inhibitory effect of pentalenolactone on vascular smooth muscle cell proliferation. Eur J Pharmacol. 2001 Jan 5;411(1-2):45-53. doi: 10.1016/s0014-2999(00)00894-3. [PubMed:11137857 ]
  3. Uyeda M, Mizukami M, Yokomizo K, Suzuki K: Pentalenolactone I and hygromycin A, immunosuppressants produced by Streptomyces filipinensis and Streptomyces hygroscopicus. Biosci Biotechnol Biochem. 2001 May;65(5):1252-4. doi: 10.1271/bbb.65.1252. [PubMed:11440152 ]