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Record Information
Version2.0
Created at2021-01-05 22:02:53 UTC
Updated at2021-07-15 17:12:37 UTC
NP-MRD IDNP0012754
Secondary Accession NumbersNone
Natural Product Identification
Common NameSaponaceolide M
Provided ByNPAtlasNPAtlas Logo
Description Saponaceolide M is found in Tricholoma terreum. Saponaceolide M was first documented in 2014 (PMID: 24753190). Based on a literature review very few articles have been published on (1S)-1-[(1S,3R)-3-{2-[(1S,2S,4R,5'S)-4-hydroxy-1,5,5-trimethyl-8-oxo-3,6-dioxaspiro[bicyclo[2.2.2]Octane-2,2'-oxane]-5'-yl]ethyl}-2,2-dimethyl-6-methylidenecyclohexyl]-2-(2-oxooxolan-3-ylidene)ethyl acetate.
Structure
Thumb
Synonyms
ValueSource
(1S)-1-[(1S,3R)-3-{2-[(1S,2S,4R,5's)-4-hydroxy-1,5,5-trimethyl-8-oxo-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxane]-5'-yl]ethyl}-2,2-dimethyl-6-methylidenecyclohexyl]-2-(2-oxooxolan-3-ylidene)ethyl acetic acidGenerator
Chemical FormulaC32H46O9
Average Mass574.7110 Da
Monoisotopic Mass574.31418 Da
IUPAC Name(1S)-1-[(1S,3R)-3-{2-[(1S,2S,4R,5'S)-4-hydroxy-1,5,5-trimethyl-8-oxo-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxane]-5'-yl]ethyl}-2,2-dimethyl-6-methylidenecyclohexyl]-2-[(3Z)-2-oxooxolan-3-ylidene]ethyl acetate
Traditional Name(1S)-1-[(1S,3R)-3-{2-[(1S,2S,4R,5'S)-4-hydroxy-1,5,5-trimethyl-8-oxo-3,6-dioxaspiro[bicyclo[2.2.2]octane-2,2'-oxane]-5'-yl]ethyl}-2,2-dimethyl-6-methylidenecyclohexyl]-2-[(3Z)-2-oxooxolan-3-ylidene]ethyl acetate
CAS Registry NumberNot Available
SMILES
CC(=O)O[C@@H](C=C1CCOC1=O)[C@H]1C(=C)CC[C@@H](CC[C@H]2CC[C@]3(OC2)O[C@@]2(O)C(=O)C[C@]3(C)OC2(C)C)C1(C)C
InChI Identifier
InChI=1S/C32H46O9/c1-19-8-10-23(28(3,4)26(19)24(39-20(2)33)16-22-13-15-37-27(22)35)11-9-21-12-14-31(38-18-21)30(7)17-25(34)32(36,41-31)29(5,6)40-30/h16,21,23-24,26,36H,1,8-15,17-18H2,2-7H3/t21-,23-,24-,26+,30-,31-,32-/m0/s1
InChI KeyCGNKJJBWOWSOJZ-OPNMGSMRSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Tricholoma terreumNPAtlas
Chemical Taxonomy
ClassificationNot classified
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
logP3.75ALOGPS
logP5.27ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)9.28ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area117.59 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity149.93 m³·mol⁻¹ChemAxon
Polarizability62.54 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
NPAtlas IDNPA002033
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID78440772
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound139583662
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yin X, Feng T, Shang JH, Zhao YL, Wang F, Li ZH, Dong ZJ, Luo XD, Liu JK: Chemical and toxicological investigations of a previously unknown poisonous European mushroom Tricholoma terreum. Chemistry. 2014 Jun 2;20(23):7001-9. doi: 10.1002/chem.201400226. Epub 2014 Apr 17. [PubMed:24753190 ]