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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 00:26:16 UTC
Update Date2022-03-07 02:56:04 UTC
HMDB IDHMDB0039080
Secondary Accession Numbers
  • HMDB39080
Metabolite Identification
Common NamePhysalin N
DescriptionPhysalin N belongs to the class of organic compounds known as physalins and derivatives. These are steroidal constituents of Physalis plants which possess an unusual 13,14-seco-16,24-cyclo-steroidal ring skeleton (where the bond that is normally present between the 13 and 14 positions in other steroids is broken while a new bond between positions 16 and 24 is formed). Based on a literature review a small amount of articles have been published on Physalin N.
Structure
Data?1563863309
SynonymsNot Available
Chemical FormulaC28H30O10
Average Molecular Weight526.5318
Monoisotopic Molecular Weight526.18389718
IUPAC Name5,16-dihydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.1¹⁸,²⁷.0¹,⁵.0²,²⁴.0⁸,¹⁷.0⁹,¹⁴.0²¹,²⁶]nonacosa-11,14-diene-4,10,22,29-tetrone
Traditional Name5,16-dihydroxy-2,9,26-trimethyl-3,19,23,28-tetraoxaoctacyclo[16.9.1.1¹⁸,²⁷.0¹,⁵.0²,²⁴.0⁸,¹⁷.0⁹,¹⁴.0²¹,²⁶]nonacosa-11,14-diene-4,10,22,29-tetrone
CAS Registry Number70286-65-6
SMILES
CC12OC(=O)C3(O)CCC4C(C(O)C=C5CC=CC(=O)C45C)C45OC13C(C4=O)C1(C)CC2OC(=O)C1CO5
InChI Identifier
InChI=1S/C28H30O10/c1-23-10-17-25(3)28-19(23)20(31)27(38-28,35-11-14(23)21(32)36-17)18-13(7-8-26(28,34)22(33)37-25)24(2)12(9-15(18)29)5-4-6-16(24)30/h4,6,9,13-15,17-19,29,34H,5,7-8,10-11H2,1-3H3
InChI KeyNYNVPVLQKXUEJM-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as physalins and derivatives. These are steroidal constituents of Physalis plants which possess an unusual 13,14-seco-16,24-cyclo-steroidal ring skeleton (where the bond that is normally present between the 13 and 14 positions in other steroids is broken while a new bond between positions 16 and 24 is formed).
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassPhysalins and derivatives
Direct ParentPhysalins and derivatives
Alternative Parents
Substituents
  • Physalin skeleton
  • Delta_valerolactone
  • Ketal
  • Oxepane
  • Cyclohexenone
  • Delta valerolactone
  • Gamma butyrolactone
  • Oxane
  • Dicarboxylic acid or derivatives
  • 3-furanone
  • Cyclic alcohol
  • Tertiary alcohol
  • Tetrahydrofuran
  • Lactone
  • Carboxylic acid ester
  • Secondary alcohol
  • Ketone
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point252 - 254 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.21 g/LALOGPS
logP1.06ALOGPS
logP1.62ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)9.08ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area145.66 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity126.86 m³·mol⁻¹ChemAxon
Polarizability52.22 ųChemAxon
Number of Rings8ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+220.04831661259
DarkChem[M-H]-208.07331661259
DeepCCS[M-2H]-252.98830932474
DeepCCS[M+Na]+228.41230932474
AllCCS[M+H]+216.332859911
AllCCS[M+H-H2O]+214.732859911
AllCCS[M+NH4]+217.832859911
AllCCS[M+Na]+218.232859911
AllCCS[M-H]-220.132859911
AllCCS[M+Na-2H]-221.232859911
AllCCS[M+HCOO]-222.532859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.5.13 minutes32390414
Predicted by Siyang on May 30, 202213.0462 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.76 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid49.8 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2606.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid178.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid164.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid146.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid84.1 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid599.9 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid597.4 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)168.1 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid985.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid387.5 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1484.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid372.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid323.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate294.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA130.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water101.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Physalin NCC12OC(=O)C3(O)CCC4C(C(O)C=C5CC=CC(=O)C45C)C45OC13C(C4=O)C1(C)CC2OC(=O)C1CO54154.1Standard polar33892256
Physalin NCC12OC(=O)C3(O)CCC4C(C(O)C=C5CC=CC(=O)C45C)C45OC13C(C4=O)C1(C)CC2OC(=O)C1CO53535.5Standard non polar33892256
Physalin NCC12OC(=O)C3(O)CCC4C(C(O)C=C5CC=CC(=O)C45C)C45OC13C(C4=O)C1(C)CC2OC(=O)C1CO54496.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Physalin N,1TMS,isomer #1CC12C(=O)C=CCC1=CC(O)C1C2CCC2(O[Si](C)(C)C)C(=O)OC3(C)C4CC5(C)C(COC16OC23C5C6=O)C(=O)O44269.8Semi standard non polar33892256
Physalin N,1TMS,isomer #1CC12C(=O)C=CCC1=CC(O)C1C2CCC2(O[Si](C)(C)C)C(=O)OC3(C)C4CC5(C)C(COC16OC23C5C6=O)C(=O)O44269.8Semi standard non polar33892256
Physalin N,1TMS,isomer #2CC12C(=O)C=CCC1=CC(O[Si](C)(C)C)C1C2CCC2(O)C(=O)OC3(C)C4CC5(C)C(COC16OC23C5C6=O)C(=O)O44230.2Semi standard non polar33892256
Physalin N,1TMS,isomer #2CC12C(=O)C=CCC1=CC(O[Si](C)(C)C)C1C2CCC2(O)C(=O)OC3(C)C4CC5(C)C(COC16OC23C5C6=O)C(=O)O44230.2Semi standard non polar33892256
Physalin N,1TMS,isomer #3CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C)C(O)(CCC1C4C(O)C=C2CC=CC(=O)C21C)C(=O)OC35C4101.6Semi standard non polar33892256
Physalin N,1TMS,isomer #3CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C)C(O)(CCC1C4C(O)C=C2CC=CC(=O)C21C)C(=O)OC35C4101.6Semi standard non polar33892256
Physalin N,2TMS,isomer #1CC12C(=O)C=CCC1=CC(O[Si](C)(C)C)C1C2CCC2(O[Si](C)(C)C)C(=O)OC3(C)C4CC5(C)C(COC16OC23C5C6=O)C(=O)O44207.4Semi standard non polar33892256
Physalin N,2TMS,isomer #1CC12C(=O)C=CCC1=CC(O[Si](C)(C)C)C1C2CCC2(O[Si](C)(C)C)C(=O)OC3(C)C4CC5(C)C(COC16OC23C5C6=O)C(=O)O44207.4Semi standard non polar33892256
Physalin N,2TMS,isomer #2CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C)C(O[Si](C)(C)C)(CCC1C4C(O)C=C2CC=CC(=O)C21C)C(=O)OC35C4085.4Semi standard non polar33892256
Physalin N,2TMS,isomer #2CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C)C(O[Si](C)(C)C)(CCC1C4C(O)C=C2CC=CC(=O)C21C)C(=O)OC35C4085.4Semi standard non polar33892256
Physalin N,2TMS,isomer #3CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C)C(O)(CCC1C4C(O[Si](C)(C)C)C=C2CC=CC(=O)C21C)C(=O)OC35C4046.0Semi standard non polar33892256
Physalin N,2TMS,isomer #3CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C)C(O)(CCC1C4C(O[Si](C)(C)C)C=C2CC=CC(=O)C21C)C(=O)OC35C4046.0Semi standard non polar33892256
Physalin N,3TMS,isomer #1CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C)C(O[Si](C)(C)C)(CCC1C4C(O[Si](C)(C)C)C=C2CC=CC(=O)C21C)C(=O)OC35C4024.0Semi standard non polar33892256
Physalin N,3TMS,isomer #1CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C)C(O[Si](C)(C)C)(CCC1C4C(O[Si](C)(C)C)C=C2CC=CC(=O)C21C)C(=O)OC35C3932.1Standard non polar33892256
Physalin N,1TBDMS,isomer #1CC12C(=O)C=CCC1=CC(O)C1C2CCC2(O[Si](C)(C)C(C)(C)C)C(=O)OC3(C)C4CC5(C)C(COC16OC23C5C6=O)C(=O)O44510.1Semi standard non polar33892256
Physalin N,1TBDMS,isomer #1CC12C(=O)C=CCC1=CC(O)C1C2CCC2(O[Si](C)(C)C(C)(C)C)C(=O)OC3(C)C4CC5(C)C(COC16OC23C5C6=O)C(=O)O44510.1Semi standard non polar33892256
Physalin N,1TBDMS,isomer #2CC12C(=O)C=CCC1=CC(O[Si](C)(C)C(C)(C)C)C1C2CCC2(O)C(=O)OC3(C)C4CC5(C)C(COC16OC23C5C6=O)C(=O)O44457.5Semi standard non polar33892256
Physalin N,1TBDMS,isomer #2CC12C(=O)C=CCC1=CC(O[Si](C)(C)C(C)(C)C)C1C2CCC2(O)C(=O)OC3(C)C4CC5(C)C(COC16OC23C5C6=O)C(=O)O44457.5Semi standard non polar33892256
Physalin N,1TBDMS,isomer #3CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C(C)(C)C)C(O)(CCC1C4C(O)C=C2CC=CC(=O)C21C)C(=O)OC35C4329.2Semi standard non polar33892256
Physalin N,1TBDMS,isomer #3CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C(C)(C)C)C(O)(CCC1C4C(O)C=C2CC=CC(=O)C21C)C(=O)OC35C4329.2Semi standard non polar33892256
Physalin N,2TBDMS,isomer #1CC12C(=O)C=CCC1=CC(O[Si](C)(C)C(C)(C)C)C1C2CCC2(O[Si](C)(C)C(C)(C)C)C(=O)OC3(C)C4CC5(C)C(COC16OC23C5C6=O)C(=O)O44677.4Semi standard non polar33892256
Physalin N,2TBDMS,isomer #1CC12C(=O)C=CCC1=CC(O[Si](C)(C)C(C)(C)C)C1C2CCC2(O[Si](C)(C)C(C)(C)C)C(=O)OC3(C)C4CC5(C)C(COC16OC23C5C6=O)C(=O)O44677.4Semi standard non polar33892256
Physalin N,2TBDMS,isomer #2CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)(CCC1C4C(O)C=C2CC=CC(=O)C21C)C(=O)OC35C4542.6Semi standard non polar33892256
Physalin N,2TBDMS,isomer #2CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)(CCC1C4C(O)C=C2CC=CC(=O)C21C)C(=O)OC35C4542.6Semi standard non polar33892256
Physalin N,2TBDMS,isomer #3CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C(C)(C)C)C(O)(CCC1C4C(O[Si](C)(C)C(C)(C)C)C=C2CC=CC(=O)C21C)C(=O)OC35C4494.3Semi standard non polar33892256
Physalin N,2TBDMS,isomer #3CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C(C)(C)C)C(O)(CCC1C4C(O[Si](C)(C)C(C)(C)C)C=C2CC=CC(=O)C21C)C(=O)OC35C4494.3Semi standard non polar33892256
Physalin N,3TBDMS,isomer #1CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)(CCC1C4C(O[Si](C)(C)C(C)(C)C)C=C2CC=CC(=O)C21C)C(=O)OC35C4691.3Semi standard non polar33892256
Physalin N,3TBDMS,isomer #1CC12CC3OC(=O)C1COC14OC5(C2=C1O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)(CCC1C4C(O[Si](C)(C)C(C)(C)C)C=C2CC=CC(=O)C21C)C(=O)OC35C4519.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Physalin N GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1920200000-6c8bb8b1ada15f17bc1c2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Physalin N GC-MS (2 TMS) - 70eV, Positivesplash10-0200-4090017000-6c2e8117c6c9561fc6032017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physalin N 10V, Positive-QTOFsplash10-0a6r-0000290000-3573f4fc6e109732cf832015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physalin N 20V, Positive-QTOFsplash10-0a6u-1100980000-e7f04a9147577b82cf2a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physalin N 40V, Positive-QTOFsplash10-0006-1100900000-7eea91de1761b7b361f82015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physalin N 10V, Negative-QTOFsplash10-004i-0000390000-0454e6c30f87d6a550c32015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physalin N 20V, Negative-QTOFsplash10-057i-0000890000-04971c966f083760077e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physalin N 40V, Negative-QTOFsplash10-000i-0840910000-279e3bdbddf48c5d84d52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physalin N 10V, Positive-QTOFsplash10-004i-0000090000-6b8f13942a0358bf3cd62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physalin N 20V, Positive-QTOFsplash10-004i-0402890000-f02c8b5994c1bd3b076a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physalin N 40V, Positive-QTOFsplash10-002o-0900100000-84fe7325d6ea062104272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physalin N 10V, Negative-QTOFsplash10-004i-0000090000-a09e301130798fa029972021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physalin N 20V, Negative-QTOFsplash10-004i-0000290000-4beaefb8e0d2592583e22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Physalin N 40V, Negative-QTOFsplash10-002b-0610930000-88c5ad4a9d5450fa92c62021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB018580
KNApSAcK IDNot Available
Chemspider ID35014741
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752539
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.