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Record Information
Version2.0
Created at2022-09-03 12:52:49 UTC
Updated at2022-09-03 12:52:49 UTC
NP-MRD IDNP0175417
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2,7-dioxo-3ah,4h,5h,6h,8bh-indeno[1,2-b]furan-4-yl acetate
Description7-Oxoorobanchyl acetate belongs to the class of organic compounds known as strigolactones. These are terpene lactones structurally characterized by the presence of an indeno[1,2-b]furan and a 2,5-dihydrofuran-2-one linked together to form a 3-methyl-5-{8-methyl-2-oxo-indeno[1,2-b]furan-3-ylidene]methoxy}-2,5-dihydrofuran-2-one skeleton. (3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2,7-dioxo-3ah,4h,5h,6h,8bh-indeno[1,2-b]furan-4-yl acetate is found in Linum usitatissimum. (3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2,7-dioxo-3ah,4h,5h,6h,8bh-indeno[1,2-b]furan-4-yl acetate was first documented in 2009 (PMID: 19502732). Based on a literature review a small amount of articles have been published on 7-Oxoorobanchyl acetate (PMID: 30280444) (PMID: 23204500).
Structure
Thumb
Synonyms
ValueSource
7-Oxoorobanchyl acetic acidGenerator
Acetate-(3as,4S,8BS,e)-8,8-dimethyl-3-(((R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yloxy)methylene)-2,7-dioxo-3,3a,4,5,6,7,8,8b-octahydro-2H-indeno(1,2-b)furan-4-yl acetateMeSH
Chemical FormulaC21H22O8
Average Mass402.3990 Da
Monoisotopic Mass402.13147 Da
IUPAC Name(3E,3aS,4S,8bS)-8,8-dimethyl-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylidene)-2,7-dioxo-2H,3H,3aH,4H,5H,6H,7H,8H,8bH-indeno[1,2-b]furan-4-yl acetate
Traditional Name(3E,3aS,4S,8bS)-8,8-dimethyl-3-({[(2R)-4-methyl-5-oxo-2H-furan-2-yl]oxy}methylidene)-2,7-dioxo-3aH,4H,5H,6H,8bH-indeno[1,2-b]furan-4-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)O[C@H]1[C@H]2[C@H](OC(=O)\C2=C\O[C@@H]2OC(=O)C(C)=C2)C2=C1CCC(=O)C2(C)C
InChI Identifier
InChI=1S/C21H22O8/c1-9-7-14(28-19(9)24)26-8-12-15-17(27-10(2)22)11-5-6-13(23)21(3,4)16(11)18(15)29-20(12)25/h7-8,14-15,17-18H,5-6H2,1-4H3/b12-8+/t14-,15+,17-,18+/m1/s1
InChI KeyGHBVBPVXEMMTGY-RMXVWQQMSA-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
Linum usitatissimumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as strigolactones. These are terpene lactones structurally characterized by the presence of an indeno[1,2-b]furan and a 2,5-dihydrofuran-2-one linked together to form a 3-methyl-5-{8-methyl-2-oxo-indeno[1,2-b]furan-3-ylidene]methoxy}-2,5-dihydrofuran-2-one skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentStrigolactones
Alternative Parents
Substituents
  • Strigolactone
  • Tricarboxylic acid or derivatives
  • Cyclohexenone
  • 2-furanone
  • Gamma butyrolactone
  • Dihydrofuran
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Vinylogous ester
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Cyclic ketone
  • Oxacycle
  • Acetal
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • 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
logP2.06ALOGPS
logP2.16ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)13.03ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area105.2 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity98.61 m³·mol⁻¹ChemAxon
Polarizability39.89 ųChemAxon
Number of Rings4ChemAxon
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 IDC00056903
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71537875
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Rial C, Varela RM, Molinillo JMG, Lopez-Raez JA, Macias FA: A new UHPLC-MS/MS method for the direct determination of strigolactones in root exudates and extracts. Phytochem Anal. 2019 Jan;30(1):110-116. doi: 10.1002/pca.2796. Epub 2018 Oct 2. [PubMed:30280444 ]
  2. Xie X, Yoneyama K, Kisugi T, Uchida K, Ito S, Akiyama K, Hayashi H, Yokota T, Nomura T, Yoneyama K: Confirming stereochemical structures of strigolactones produced by rice and tobacco. Mol Plant. 2013 Jan;6(1):153-63. doi: 10.1093/mp/sss139. Epub 2012 Nov 30. [PubMed:23204500 ]
  3. Xie X, Yoneyama K, Kurita JY, Harada Y, Yamada Y, Takeuchi Y, Yoneyama K: 7-Oxoorobanchyl acetate and 7-Oxoorobanchol as germination stimulants for root parasitic plants from flax (Linum usitatissimum). Biosci Biotechnol Biochem. 2009 Jun;73(6):1367-70. doi: 10.1271/bbb.90021. Epub 2009 Jun 7. [PubMed:19502732 ]
  4. LOTUS database [Link]