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Record Information
Version2.0
Created at2022-09-04 12:08:37 UTC
Updated at2022-09-04 12:08:37 UTC
NP-MRD IDNP0194485
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3r,4r,5s)-5-[(1r,3'r,3ar,3bs,5ar,9ar,9br,11ar)-3',9a,11a-trimethyl-7-oxo-dodecahydro-2h-spiro[cyclopenta[a]phenanthrene-1,2'-oxiran]-3'-yl]-5-(acetyloxy)-2,3,4-trimethylpentan-2-yl acetate
Description(3R,4R,5S)-5-(acetyloxy)-2,3,4-trimethyl-5-[(1'R,2R,2'R,3R,7'R,10'S,11'R,15'R)-2',3,15'-trimethyl-5'-oxospiro[oxirane-2,14'-tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane]-3-yl]pentan-2-yl acetate belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. (3r,4r,5s)-5-[(1r,3'r,3ar,3bs,5ar,9ar,9br,11ar)-3',9a,11a-trimethyl-7-oxo-dodecahydro-2h-spiro[cyclopenta[a]phenanthrene-1,2'-oxiran]-3'-yl]-5-(acetyloxy)-2,3,4-trimethylpentan-2-yl acetate is found in Isis hippuris. Based on a literature review very few articles have been published on (3R,4R,5S)-5-(acetyloxy)-2,3,4-trimethyl-5-[(1'R,2R,2'R,3R,7'R,10'S,11'R,15'R)-2',3,15'-trimethyl-5'-oxospiro[oxirane-2,14'-tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecane]-3-yl]pentan-2-yl acetate.
Structure
Thumb
Synonyms
ValueSource
(3R,4R,5S)-5-(Acetyloxy)-2,3,4-trimethyl-5-[(1'r,2R,2'r,3R,7'r,10's,11'r,15'r)-2',3,15'-trimethyl-5'-oxospiro[oxirane-2,14'-tetracyclo[8.7.0.0,.0,]heptadecane]-3-yl]pentan-2-yl acetic acidGenerator
Chemical FormulaC33H52O6
Average Mass544.7730 Da
Monoisotopic Mass544.37639 Da
IUPAC Name(3R,4R,5S)-5-(acetyloxy)-2,3,4-trimethyl-5-[(1'R,2R,2'R,3R,7'R,10'S,11'R,15'R)-2',3,15'-trimethyl-5'-oxospiro[oxirane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-3-yl]pentan-2-yl acetate
Traditional Name(3R,4R,5S)-5-(acetyloxy)-2,3,4-trimethyl-5-[(1'R,2R,2'R,3R,7'R,10'S,11'R,15'R)-2',3,15'-trimethyl-5'-oxospiro[oxirane-2,14'-tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecane]-3-yl]pentan-2-yl acetate
CAS Registry NumberNot Available
SMILES
C[C@H]([C@@H](C)C(C)(C)OC(C)=O)[C@H](OC(C)=O)[C@@]1(C)O[C@@]11CC[C@@H]2[C@H]3CC[C@@H]4CC(=O)CC[C@@]4(C)[C@@H]3CC[C@@]12C
InChI Identifier
InChI=1S/C33H52O6/c1-19(20(2)29(5,6)38-22(4)35)28(37-21(3)34)32(9)33(39-32)17-14-27-25-11-10-23-18-24(36)12-15-30(23,7)26(25)13-16-31(27,33)8/h19-20,23,25-28H,10-18H2,1-9H3/t19-,20-,23-,25+,26-,27-,28+,30-,31-,32-,33-/m1/s1
InChI KeyFVZOEIVUTGXCOH-BEEHKQQLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Isis hippurisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassErgostane steroids
Direct ParentErgosterols and derivatives
Alternative Parents
Substituents
  • Ergosterol-skeleton
  • 3-oxosteroid
  • 3-oxo-5-beta-steroid
  • Oxosteroid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Ketone
  • Cyclic ketone
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen 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
logP5.71ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area82.2 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity148.65 m³·mol⁻¹ChemAxon
Polarizability62.56 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
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 Compound162893756
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]