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Record Information
Version2.0
Created at2024-02-15 20:04:31 UTC
Updated at2024-09-03 04:19:27 UTC
NP-MRD IDNP0332510
Natural Product DOIhttps://doi.org/10.57994/1763
Secondary Accession NumbersNone
Natural Product Identification
Common NameRubescin O
DescriptionRubescin O belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Based on a literature review a small amount of articles have been published on Rubescin O.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC33H34O7
Average Mass542.6280 Da
Monoisotopic Mass542.23045 Da
IUPAC Name(1S,2S,4S,6S,7S,9R,11R,12S,13S,14R,17R,21S)-7-(furan-3-yl)-1,6,12,17-tetramethyl-20-oxo-3,10,15-trioxaheptacyclo[12.6.1.0^{2,4}.0^{2,12}.0^{6,11}.0^{9,11}.0^{17,21}]henicos-18-en-13-yl benzoate
Traditional Name(1S,2S,4S,6S,7S,9R,11R,12S,13S,14R,17R,21S)-7-(furan-3-yl)-1,6,12,17-tetramethyl-20-oxo-3,10,15-trioxaheptacyclo[12.6.1.0^{2,4}.0^{2,12}.0^{6,11}.0^{9,11}.0^{17,21}]henicos-18-en-13-yl benzoate
CAS Registry NumberNot Available
SMILES
[H][C@]12[C@H]3OC[C@]1(C)C=CC(=O)[C@]2(C)[C@]12O[C@H]1C[C@@]1(C)[C@@H](C[C@H]4O[C@@]14[C@]2(C)[C@@H]3OC(=O)C1=CC=CC=C1)C1=COC=C1
InChI Identifier
InChI=1S/C33H34O7/c1-28-12-10-21(34)30(3)25(28)24(37-17-28)26(38-27(35)18-8-6-5-7-9-18)31(4)32-22(39-32)14-20(19-11-13-36-16-19)29(32,2)15-23-33(30,31)40-23/h5-13,16,20,22-26H,14-15,17H2,1-4H3/t20-,22+,23-,24+,25-,26+,28-,29-,30-,31-,32+,33+/m0/s1
InChI KeyDHLDTTSSYDCWEF-OUJBNORMSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)kngoto@p.kanazawa-u.ac.jpNot AvailableNot Available2024-02-15View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCL3, experimental)kngoto@p.kanazawa-u.ac.jpNot AvailableNot Available2024-02-15View Spectrum
NOESY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)kngoto@p.kanazawa-u.ac.jpNot AvailableNot Available2024-02-15View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, CDCL3, experimental)kngoto@p.kanazawa-u.ac.jpNot AvailableNot Available2024-02-15View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)kngoto@p.kanazawa-u.ac.jpNot AvailableNot Available2024-02-15View Spectrum
HMQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)kngoto@p.kanazawa-u.ac.jpNot AvailableNot Available2024-02-15View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentLimonoids
Alternative Parents
Substituents
  • Limonoid skeleton
  • Thromboxane
  • Steroid ester
  • Eicosanoid
  • Naphthopyran
  • Naphthofuran
  • Fatty alcohol ester
  • Naphthalene
  • Benzoate ester
  • Benzoic acid or derivatives
  • Benzoyl
  • Cyclohexenone
  • Oxepane
  • Fatty acid ester
  • Fatty acyl
  • Benzenoid
  • Pyran
  • Oxane
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Alpha,beta-unsaturated ketone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Furan
  • Enone
  • Acryloyl-group
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Oxirane
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
logP4.92ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area90.8 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity143.23 m³·mol⁻¹ChemAxon
Polarizability56.12 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References