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Record Information
Version2.0
Created at2022-09-11 12:44:49 UTC
Updated at2022-09-11 12:44:50 UTC
NP-MRD IDNP0314577
Secondary Accession NumbersNone
Natural Product Identification
Common Name(4r)-4-[(1'r,2'r,3r,3ar,4r,4'r,7as,8's,12's,15's)-15'-(acetyloxy)-4-hydroxy-2',6,11'-trimethyl-7'-methylidene-2,6'-dioxo-3a,4,7,7a-tetrahydro-5'-oxaspiro[1-benzofuran-3,13'-tetracyclo[10.2.1.0¹,¹⁰.0⁴,⁸]pentadecan]-10'-en-5-yl]pentyl acetate
Description(4R)-4-[(1'R,2'R,3R,3aR,4R,4'R,7aS,8'S,12'S,15'S)-15'-(acetyloxy)-4-hydroxy-2',6,11'-trimethyl-7'-methylidene-2,6'-dioxo-3a,4,7,7a-tetrahydro-2H-5'-oxaspiro[1-benzofuran-3,13'-tetracyclo[10.2.1.0¹,¹⁰.0⁴,⁸]Pentadecan]-10'-en-5-yl]pentyl acetate belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. (4r)-4-[(1'r,2'r,3r,3ar,4r,4'r,7as,8's,12's,15's)-15'-(acetyloxy)-4-hydroxy-2',6,11'-trimethyl-7'-methylidene-2,6'-dioxo-3a,4,7,7a-tetrahydro-5'-oxaspiro[1-benzofuran-3,13'-tetracyclo[10.2.1.0¹,¹⁰.0⁴,⁸]pentadecan]-10'-en-5-yl]pentyl acetate is found in Pentanema britannicum. Based on a literature review very few articles have been published on (4R)-4-[(1'R,2'R,3R,3aR,4R,4'R,7aS,8'S,12'S,15'S)-15'-(acetyloxy)-4-hydroxy-2',6,11'-trimethyl-7'-methylidene-2,6'-dioxo-3a,4,7,7a-tetrahydro-2H-5'-oxaspiro[1-benzofuran-3,13'-tetracyclo[10.2.1.0¹,¹⁰.0⁴,⁸]Pentadecan]-10'-en-5-yl]pentyl acetate.
Structure
Thumb
Synonyms
ValueSource
(4R)-4-[(1'r,2'r,3R,3AR,4R,4'r,7as,8's,12's,15's)-15'-(acetyloxy)-4-hydroxy-2',6,11'-trimethyl-7'-methylidene-2,6'-dioxo-3a,4,7,7a-tetrahydro-2H-5'-oxaspiro[1-benzofuran-3,13'-tetracyclo[10.2.1.0,.0,]pentadecan]-10'-en-5-yl]pentyl acetic acidGenerator
Chemical FormulaC34H44O9
Average Mass596.7170 Da
Monoisotopic Mass596.29853 Da
IUPAC Name(4R)-4-[(1'R,2'R,3R,3aR,4R,4'R,7aS,8'S,12'S,15'S)-15'-(acetyloxy)-4-hydroxy-2',6,11'-trimethyl-7'-methylidene-2,6'-dioxo-3a,4,7,7a-tetrahydro-2H-5'-oxaspiro[1-benzofuran-3,13'-tetracyclo[10.2.1.0^{1,10}.0^{4,8}]pentadecan]-10'-en-5-yl]pentyl acetate
Traditional Name(4R)-4-[(1'R,2'R,3R,3aR,4R,4'R,7aS,8'S,12'S,15'S)-15'-(acetyloxy)-4-hydroxy-2',6,11'-trimethyl-7'-methylidene-2,6'-dioxo-3a,4,7,7a-tetrahydro-5'-oxaspiro[1-benzofuran-3,13'-tetracyclo[10.2.1.0^{1,10}.0^{4,8}]pentadecan]-10'-en-5-yl]pentyl acetate
CAS Registry NumberNot Available
SMILES
C[C@H](CCCOC(C)=O)C1=C(C)C[C@@H]2OC(=O)[C@@]3(C[C@]45[C@@H](OC(C)=O)[C@H]3C(C)=C4C[C@@H]3[C@@H](C[C@H]5C)OC(=O)C3=C)[C@@H]2[C@H]1O
InChI Identifier
InChI=1S/C34H44O9/c1-15(9-8-10-40-20(6)35)26-16(2)11-25-28(29(26)37)34(32(39)43-25)14-33-17(3)12-24-22(18(4)31(38)42-24)13-23(33)19(5)27(34)30(33)41-21(7)36/h15,17,22,24-25,27-30,37H,4,8-14H2,1-3,5-7H3/t15-,17-,22+,24-,25+,27-,28+,29+,30+,33-,34-/m1/s1
InChI KeyFPZMKWNKHQRDMW-RSQKRGDPSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Pentanema britannicumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Terpene lactone
  • Sesquiterpenoid
  • Tetracarboxylic acid or derivatives
  • Benzofuran
  • Gamma butyrolactone
  • Alpha,beta-unsaturated carboxylic ester
  • Tetrahydrofuran
  • Enoate ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • 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
logP2.95ChemAxon
pKa (Strongest Acidic)14.22ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area125.43 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity155.41 m³·mol⁻¹ChemAxon
Polarizability64.17 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162940737
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]