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Record Information
Version2.0
Created at2022-09-04 08:50:13 UTC
Updated at2022-09-04 08:50:13 UTC
NP-MRD IDNP0191772
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,2s,5r,5'ar,8'ar,9'r,10'r,11'as,11'bs)-9'-hydroxy-8'a,9'-dimethyl-3,3',7'-trioxo-5',5'a,8',10',11',11'b-hexahydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,6'-phenaleno[3,3a-c]furan]-10'-yl acetate
Description(1S,1'S,2S,3'R,4'R,5R,5'R,9'R,16'S)-4'-hydroxy-4',5'-dimethyl-3,7',13'-trioxo-4,6,14'-trioxaspiro[bicyclo[3.1.0]Hexane-2,8'-tetracyclo[7.6.1.0¹,¹².0⁵,¹⁶]Hexadecan]-11'-en-3'-yl acetate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. (1s,2s,5r,5'ar,8'ar,9'r,10'r,11'as,11'bs)-9'-hydroxy-8'a,9'-dimethyl-3,3',7'-trioxo-5',5'a,8',10',11',11'b-hexahydro-1'h-4,6-dioxaspiro[bicyclo[3.1.0]hexane-2,6'-phenaleno[3,3a-c]furan]-10'-yl acetate is found in Salvia languidula. Based on a literature review very few articles have been published on (1S,1'S,2S,3'R,4'R,5R,5'R,9'R,16'S)-4'-hydroxy-4',5'-dimethyl-3,7',13'-trioxo-4,6,14'-trioxaspiro[bicyclo[3.1.0]Hexane-2,8'-tetracyclo[7.6.1.0¹,¹².0⁵,¹⁶]Hexadecan]-11'-en-3'-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(1S,1's,2S,3'r,4'r,5R,5'r,9'r,16's)-4'-Hydroxy-4',5'-dimethyl-3,7',13'-trioxo-4,6,14'-trioxaspiro[bicyclo[3.1.0]hexane-2,8'-tetracyclo[7.6.1.0,.0,]hexadecan]-11'-en-3'-yl acetic acidGenerator
Chemical FormulaC22H24O9
Average Mass432.4250 Da
Monoisotopic Mass432.14203 Da
IUPAC Name(1S,1'S,2S,3'R,4'R,5R,5'R,9'R,16'S)-4'-hydroxy-4',5'-dimethyl-3,7',13'-trioxo-4,6,14'-trioxaspiro[bicyclo[3.1.0]hexane-2,8'-tetracyclo[7.6.1.0^{1,12}.0^{5,16}]hexadecan]-11'-en-3'-yl acetate
Traditional Name(1S,1'S,2S,3'R,4'R,5R,5'R,9'R,16'S)-4'-hydroxy-4',5'-dimethyl-3,7',13'-trioxo-4,6,14'-trioxaspiro[bicyclo[3.1.0]hexane-2,8'-tetracyclo[7.6.1.0^{1,12}.0^{5,16}]hexadecan]-11'-en-3'-yl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)O[C@@H]1C[C@@]23COC(=O)C2=CC[C@@H]2[C@@H]3[C@@](C)(CC(=O)[C@@]22[C@@H]3O[C@@H]3OC2=O)[C@@]1(C)O
InChI Identifier
InChI=1S/C22H24O9/c1-9(23)29-13-7-21-8-28-16(25)11(21)5-4-10-14(21)19(2,20(13,3)27)6-12(24)22(10)15-17(30-15)31-18(22)26/h5,10,13-15,17,27H,4,6-8H2,1-3H3/t10-,13-,14-,15-,17-,19-,20+,21-,22-/m1/s1
InChI KeyVSPWQYYVQCZYOG-FHUFOXDZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Salvia languidulaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassTricarboxylic acids and derivatives
Direct ParentTricarboxylic acids and derivatives
Alternative Parents
Substituents
  • Tricarboxylic acid or derivatives
  • Meta-dioxane
  • Gamma butyrolactone
  • Cyclic alcohol
  • Tertiary alcohol
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxirane
  • Organoheterocyclic compound
  • Oxacycle
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • 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
logP0.59ChemAxon
pKa (Strongest Acidic)13.61ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area128.73 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity100.21 m³·mol⁻¹ChemAxon
Polarizability41.23 ųChemAxon
Number of Rings6ChemAxon
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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162892853
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]