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Record Information
Version2.0
Created at2022-09-11 20:16:04 UTC
Updated at2022-09-11 20:16:04 UTC
NP-MRD IDNP0319307
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate
DescriptionPhysagulin G belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. Physagulin G is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, physagulin g has been detected, but not quantified in, fruits and herbs and spices. 2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate is found in Physalis angulata. This could make physagulin g a potential biomarker for the consumption of these foods.
Structure
Thumb
Synonyms
ValueSource
2,16,17-Trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,6-dihydro-2H-pyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetic acidGenerator
Chemical FormulaC36H50O15
Average Mass722.7732 Da
Monoisotopic Mass722.31497 Da
IUPAC Name2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-3,6-dihydro-2H-pyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate
Traditional Name2,16,17-trihydroxy-7,11-dimethyl-6-{1-[5-methyl-6-oxo-4-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-2,3-dihydropyran-2-yl]ethyl}-12-oxo-5-oxapentacyclo[8.8.0.0²,⁷.0⁴,⁶.0¹¹,¹⁶]octadec-13-en-3-yl acetate
CAS Registry NumberNot Available
SMILES
CC(C1CC(COC2OC(CO)C(O)C(O)C2O)=C(C)C(=O)O1)C12OC1C(OC(C)=O)C1(O)C3CC(O)C4(O)CC=CC(=O)C4(C)C3CCC21C
InChI Identifier
InChI=1S/C36H50O15/c1-15-18(14-47-31-27(43)26(42)25(41)22(13-37)50-31)11-21(49-30(15)44)16(2)36-29(51-36)28(48-17(3)38)35(46)20-12-24(40)34(45)9-6-7-23(39)33(34,5)19(20)8-10-32(35,36)4/h6-7,16,19-22,24-29,31,37,40-43,45-46H,8-14H2,1-5H3
InChI KeyLBNOIKRBLYMNFW-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Physalis angulataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentWithanolides and derivatives
Alternative ParentsNot Available
SubstituentsNot Available
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
logP0.24ALOGPS
logP-0.87ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)12.11ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area242.27 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity172.85 m³·mol⁻¹ChemAxon
Polarizability74.09 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0039694
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019323
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752708
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]