Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:50 UTC
Update Date2022-03-07 02:49:15 UTC
HMDB IDHMDB0002363
Secondary Accession Numbers
  • HMDB02363
Metabolite Identification
Common NameLevuglandin E2
DescriptionLevuglandin E2 is a levuglandin generated in the cyclooxygenase (COX) pathway. Levuglandins (LGs) and their stereo and structural isomers are extraordinarily reactive γ-ketoaldehydes that are generated by rearrangements of prostanoid endoperoxide intermediates of polyene cyclooxygenation. Their rapid adduction with biological nucleophiles results, inter alia, in pathological modifications of proteins and DNA. It also complicates their detection. Cyclooxygenase-promoted lipid oxidation is a pivotal step in the biosynthesis of an array of physiologically active metabolites. COX fosters a highly regio and stereoselective cyclooxygenation of arachidonic acid (AA) to deliver a single, enantiomerically pure endoperoxide, PGH2, that is a branch point in the biosynthesis of numerous hormone-like mediators of cellular activities. Spontaneous rearrangements of PGH2 were known to generate prostaglandins (PG) PGD2 and PGE2. (PMID: 15752459 ).
Structure
Data?1582752245
Synonyms
ValueSource
10,11-Seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoateHMDB
10,11-Seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoic acidHMDB
LGE2HMDB
Chemical FormulaC20H32O5
Average Molecular Weight352.4651
Monoisotopic Molecular Weight352.224974134
IUPAC Name(5Z,8S,9R,10E,12S)-8-acetyl-9-formyl-12-hydroxyheptadeca-5,10-dienoic acid
Traditional Name(5Z,8S,9R,10E,12S)-8-acetyl-9-formyl-12-hydroxyheptadeca-5,10-dienoic acid
CAS Registry Number91712-41-3
SMILES
CCCCC[C@H](O)\C=C\[C@@H](C=O)[C@H](C\C=C/CCCC(O)=O)C(C)=O
InChI Identifier
InChI=1S/C20H32O5/c1-3-4-7-10-18(23)14-13-17(15-21)19(16(2)22)11-8-5-6-9-12-20(24)25/h5,8,13-15,17-19,23H,3-4,6-7,9-12H2,1-2H3,(H,24,25)/b8-5-,14-13+/t17-,18-,19+/m0/s1
InChI KeyWJWAORNTZNRHBP-LBONXFAWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Unsaturated fatty acid
  • Ketone
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.024 g/LALOGPS
logP3.52ALOGPS
logP3.36ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity100.54 m³·mol⁻¹ChemAxon
Polarizability40.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+187.5831661259
DarkChem[M-H]-192.04331661259
DeepCCS[M+H]+191.68730932474
DeepCCS[M-H]-189.29130932474
DeepCCS[M-2H]-222.46330932474
DeepCCS[M+Na]+197.59930932474
AllCCS[M+H]+194.432859911
AllCCS[M+H-H2O]+191.732859911
AllCCS[M+NH4]+196.932859911
AllCCS[M+Na]+197.632859911
AllCCS[M-H]-190.232859911
AllCCS[M+Na-2H]-191.832859911
AllCCS[M+HCOO]-193.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Levuglandin E2CCCCC[C@H](O)\C=C\[C@@H](C=O)[C@H](C\C=C/CCCC(O)=O)C(C)=O4111.4Standard polar33892256
Levuglandin E2CCCCC[C@H](O)\C=C\[C@@H](C=O)[C@H](C\C=C/CCCC(O)=O)C(C)=O2485.4Standard non polar33892256
Levuglandin E2CCCCC[C@H](O)\C=C\[C@@H](C=O)[C@H](C\C=C/CCCC(O)=O)C(C)=O2659.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Levuglandin E2,1TMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](C=O)[C@H](C/C=C\CCCC(=O)O)C(C)=O)O[Si](C)(C)C2725.2Semi standard non polar33892256
Levuglandin E2,1TMS,isomer #2CCCCC[C@H](O)/C=C/[C@@H](C=O)[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)C(C)=O2681.8Semi standard non polar33892256
Levuglandin E2,1TMS,isomer #3CCCCC[C@H](O)/C=C/[C@@H](C=O)C(C/C=C\CCCC(=O)O)=C(C)O[Si](C)(C)C2733.2Semi standard non polar33892256
Levuglandin E2,1TMS,isomer #4C=C(O[Si](C)(C)C)[C@@H](C/C=C\CCCC(=O)O)[C@H](C=O)/C=C/[C@@H](O)CCCCC2705.0Semi standard non polar33892256
Levuglandin E2,1TMS,isomer #5CCCCC[C@H](O)/C=C/C(=CO[Si](C)(C)C)[C@H](C/C=C\CCCC(=O)O)C(C)=O2827.8Semi standard non polar33892256
Levuglandin E2,2TMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](C=O)[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)C(C)=O)O[Si](C)(C)C2691.0Semi standard non polar33892256
Levuglandin E2,2TMS,isomer #2CCCCC[C@@H](/C=C/[C@@H](C=O)C(C/C=C\CCCC(=O)O)=C(C)O[Si](C)(C)C)O[Si](C)(C)C2787.1Semi standard non polar33892256
Levuglandin E2,2TMS,isomer #3C=C(O[Si](C)(C)C)[C@@H](C/C=C\CCCC(=O)O)[C@H](C=O)/C=C/[C@H](CCCCC)O[Si](C)(C)C2737.9Semi standard non polar33892256
Levuglandin E2,2TMS,isomer #4CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C)[C@H](C/C=C\CCCC(=O)O)C(C)=O)O[Si](C)(C)C2888.2Semi standard non polar33892256
Levuglandin E2,2TMS,isomer #5CCCCC[C@H](O)/C=C/[C@@H](C=O)C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(C)O[Si](C)(C)C2719.7Semi standard non polar33892256
Levuglandin E2,2TMS,isomer #6C=C(O[Si](C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@H](C=O)/C=C/[C@@H](O)CCCCC2710.7Semi standard non polar33892256
Levuglandin E2,2TMS,isomer #7CCCCC[C@H](O)/C=C/C(=CO[Si](C)(C)C)[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)C(C)=O2812.9Semi standard non polar33892256
Levuglandin E2,2TMS,isomer #8CCCCC[C@H](O)/C=C/C(=CO[Si](C)(C)C)C(C/C=C\CCCC(=O)O)=C(C)O[Si](C)(C)C2976.8Semi standard non polar33892256
Levuglandin E2,2TMS,isomer #9C=C(O[Si](C)(C)C)[C@@H](C/C=C\CCCC(=O)O)C(=CO[Si](C)(C)C)/C=C/[C@@H](O)CCCCC2883.1Semi standard non polar33892256
Levuglandin E2,3TMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](C=O)C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(C)O[Si](C)(C)C)O[Si](C)(C)C2741.0Semi standard non polar33892256
Levuglandin E2,3TMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](C=O)C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(C)O[Si](C)(C)C)O[Si](C)(C)C2652.8Standard non polar33892256
Levuglandin E2,3TMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](C=O)C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(C)O[Si](C)(C)C)O[Si](C)(C)C2725.8Standard polar33892256
Levuglandin E2,3TMS,isomer #2C=C(O[Si](C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@H](C=O)/C=C/[C@H](CCCCC)O[Si](C)(C)C2700.1Semi standard non polar33892256
Levuglandin E2,3TMS,isomer #2C=C(O[Si](C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@H](C=O)/C=C/[C@H](CCCCC)O[Si](C)(C)C2631.9Standard non polar33892256
Levuglandin E2,3TMS,isomer #2C=C(O[Si](C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C)[C@H](C=O)/C=C/[C@H](CCCCC)O[Si](C)(C)C2760.1Standard polar33892256
Levuglandin E2,3TMS,isomer #3CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C)[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)C(C)=O)O[Si](C)(C)C2862.8Semi standard non polar33892256
Levuglandin E2,3TMS,isomer #3CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C)[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)C(C)=O)O[Si](C)(C)C2596.9Standard non polar33892256
Levuglandin E2,3TMS,isomer #3CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C)[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C)C(C)=O)O[Si](C)(C)C2929.3Standard polar33892256
Levuglandin E2,3TMS,isomer #4CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C)C(C/C=C\CCCC(=O)O)=C(C)O[Si](C)(C)C)O[Si](C)(C)C3020.2Semi standard non polar33892256
Levuglandin E2,3TMS,isomer #4CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C)C(C/C=C\CCCC(=O)O)=C(C)O[Si](C)(C)C)O[Si](C)(C)C2569.2Standard non polar33892256
Levuglandin E2,3TMS,isomer #4CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C)C(C/C=C\CCCC(=O)O)=C(C)O[Si](C)(C)C)O[Si](C)(C)C3159.4Standard polar33892256
Levuglandin E2,3TMS,isomer #5C=C(O[Si](C)(C)C)[C@@H](C/C=C\CCCC(=O)O)C(=CO[Si](C)(C)C)/C=C/[C@H](CCCCC)O[Si](C)(C)C2925.6Semi standard non polar33892256
Levuglandin E2,3TMS,isomer #5C=C(O[Si](C)(C)C)[C@@H](C/C=C\CCCC(=O)O)C(=CO[Si](C)(C)C)/C=C/[C@H](CCCCC)O[Si](C)(C)C2543.8Standard non polar33892256
Levuglandin E2,3TMS,isomer #5C=C(O[Si](C)(C)C)[C@@H](C/C=C\CCCC(=O)O)C(=CO[Si](C)(C)C)/C=C/[C@H](CCCCC)O[Si](C)(C)C3209.3Standard polar33892256
Levuglandin E2,3TMS,isomer #6CCCCC[C@H](O)/C=C/C(=CO[Si](C)(C)C)C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(C)O[Si](C)(C)C2956.2Semi standard non polar33892256
Levuglandin E2,3TMS,isomer #6CCCCC[C@H](O)/C=C/C(=CO[Si](C)(C)C)C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(C)O[Si](C)(C)C2645.1Standard non polar33892256
Levuglandin E2,3TMS,isomer #6CCCCC[C@H](O)/C=C/C(=CO[Si](C)(C)C)C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(C)O[Si](C)(C)C3229.2Standard polar33892256
Levuglandin E2,3TMS,isomer #7C=C(O[Si](C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C)C(=CO[Si](C)(C)C)/C=C/[C@@H](O)CCCCC2868.2Semi standard non polar33892256
Levuglandin E2,3TMS,isomer #7C=C(O[Si](C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C)C(=CO[Si](C)(C)C)/C=C/[C@@H](O)CCCCC2621.0Standard non polar33892256
Levuglandin E2,3TMS,isomer #7C=C(O[Si](C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C)C(=CO[Si](C)(C)C)/C=C/[C@@H](O)CCCCC3286.7Standard polar33892256
Levuglandin E2,4TMS,isomer #1CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C)C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(C)O[Si](C)(C)C)O[Si](C)(C)C2964.4Semi standard non polar33892256
Levuglandin E2,4TMS,isomer #1CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C)C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(C)O[Si](C)(C)C)O[Si](C)(C)C2631.0Standard non polar33892256
Levuglandin E2,4TMS,isomer #1CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C)C(C/C=C\CCCC(=O)O[Si](C)(C)C)=C(C)O[Si](C)(C)C)O[Si](C)(C)C2880.5Standard polar33892256
Levuglandin E2,4TMS,isomer #2C=C(O[Si](C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C)C(=CO[Si](C)(C)C)/C=C/[C@H](CCCCC)O[Si](C)(C)C2893.0Semi standard non polar33892256
Levuglandin E2,4TMS,isomer #2C=C(O[Si](C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C)C(=CO[Si](C)(C)C)/C=C/[C@H](CCCCC)O[Si](C)(C)C2609.3Standard non polar33892256
Levuglandin E2,4TMS,isomer #2C=C(O[Si](C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C)C(=CO[Si](C)(C)C)/C=C/[C@H](CCCCC)O[Si](C)(C)C2913.4Standard polar33892256
Levuglandin E2,1TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](C=O)[C@H](C/C=C\CCCC(=O)O)C(C)=O)O[Si](C)(C)C(C)(C)C2964.4Semi standard non polar33892256
Levuglandin E2,1TBDMS,isomer #2CCCCC[C@H](O)/C=C/[C@@H](C=O)[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=O2936.4Semi standard non polar33892256
Levuglandin E2,1TBDMS,isomer #3CCCCC[C@H](O)/C=C/[C@@H](C=O)C(C/C=C\CCCC(=O)O)=C(C)O[Si](C)(C)C(C)(C)C2963.6Semi standard non polar33892256
Levuglandin E2,1TBDMS,isomer #4C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C/C=C\CCCC(=O)O)[C@H](C=O)/C=C/[C@@H](O)CCCCC2943.6Semi standard non polar33892256
Levuglandin E2,1TBDMS,isomer #5CCCCC[C@H](O)/C=C/C(=CO[Si](C)(C)C(C)(C)C)[C@H](C/C=C\CCCC(=O)O)C(C)=O3047.1Semi standard non polar33892256
Levuglandin E2,2TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](C=O)[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=O)O[Si](C)(C)C(C)(C)C3213.7Semi standard non polar33892256
Levuglandin E2,2TBDMS,isomer #2CCCCC[C@@H](/C=C/[C@@H](C=O)C(C/C=C\CCCC(=O)O)=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3222.8Semi standard non polar33892256
Levuglandin E2,2TBDMS,isomer #3C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C/C=C\CCCC(=O)O)[C@H](C=O)/C=C/[C@H](CCCCC)O[Si](C)(C)C(C)(C)C3191.1Semi standard non polar33892256
Levuglandin E2,2TBDMS,isomer #4CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C(C)(C)C)[C@H](C/C=C\CCCC(=O)O)C(C)=O)O[Si](C)(C)C(C)(C)C3309.9Semi standard non polar33892256
Levuglandin E2,2TBDMS,isomer #5CCCCC[C@H](O)/C=C/[C@@H](C=O)C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C3178.9Semi standard non polar33892256
Levuglandin E2,2TBDMS,isomer #6C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@H](C=O)/C=C/[C@@H](O)CCCCC3171.3Semi standard non polar33892256
Levuglandin E2,2TBDMS,isomer #7CCCCC[C@H](O)/C=C/C(=CO[Si](C)(C)C(C)(C)C)[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=O3265.0Semi standard non polar33892256
Levuglandin E2,2TBDMS,isomer #8CCCCC[C@H](O)/C=C/C(=CO[Si](C)(C)C(C)(C)C)C(C/C=C\CCCC(=O)O)=C(C)O[Si](C)(C)C(C)(C)C3429.6Semi standard non polar33892256
Levuglandin E2,2TBDMS,isomer #9C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C/C=C\CCCC(=O)O)C(=CO[Si](C)(C)C(C)(C)C)/C=C/[C@@H](O)CCCCC3319.9Semi standard non polar33892256
Levuglandin E2,3TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](C=O)C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3450.9Semi standard non polar33892256
Levuglandin E2,3TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](C=O)C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3162.6Standard non polar33892256
Levuglandin E2,3TBDMS,isomer #1CCCCC[C@@H](/C=C/[C@@H](C=O)C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2958.3Standard polar33892256
Levuglandin E2,3TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@H](C=O)/C=C/[C@H](CCCCC)O[Si](C)(C)C(C)(C)C3405.3Semi standard non polar33892256
Levuglandin E2,3TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@H](C=O)/C=C/[C@H](CCCCC)O[Si](C)(C)C(C)(C)C3145.0Standard non polar33892256
Levuglandin E2,3TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)[C@H](C=O)/C=C/[C@H](CCCCC)O[Si](C)(C)C(C)(C)C2972.5Standard polar33892256
Levuglandin E2,3TBDMS,isomer #3CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C(C)(C)C)[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=O)O[Si](C)(C)C(C)(C)C3528.9Semi standard non polar33892256
Levuglandin E2,3TBDMS,isomer #3CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C(C)(C)C)[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=O)O[Si](C)(C)C(C)(C)C3097.0Standard non polar33892256
Levuglandin E2,3TBDMS,isomer #3CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C(C)(C)C)[C@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(C)=O)O[Si](C)(C)C(C)(C)C3113.8Standard polar33892256
Levuglandin E2,3TBDMS,isomer #4CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C(C)(C)C)C(C/C=C\CCCC(=O)O)=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3669.0Semi standard non polar33892256
Levuglandin E2,3TBDMS,isomer #4CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C(C)(C)C)C(C/C=C\CCCC(=O)O)=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3072.8Standard non polar33892256
Levuglandin E2,3TBDMS,isomer #4CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C(C)(C)C)C(C/C=C\CCCC(=O)O)=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3333.4Standard polar33892256
Levuglandin E2,3TBDMS,isomer #5C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C/C=C\CCCC(=O)O)C(=CO[Si](C)(C)C(C)(C)C)/C=C/[C@H](CCCCC)O[Si](C)(C)C(C)(C)C3560.3Semi standard non polar33892256
Levuglandin E2,3TBDMS,isomer #5C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C/C=C\CCCC(=O)O)C(=CO[Si](C)(C)C(C)(C)C)/C=C/[C@H](CCCCC)O[Si](C)(C)C(C)(C)C3054.1Standard non polar33892256
Levuglandin E2,3TBDMS,isomer #5C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C/C=C\CCCC(=O)O)C(=CO[Si](C)(C)C(C)(C)C)/C=C/[C@H](CCCCC)O[Si](C)(C)C(C)(C)C3353.5Standard polar33892256
Levuglandin E2,3TBDMS,isomer #6CCCCC[C@H](O)/C=C/C(=CO[Si](C)(C)C(C)(C)C)C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C3627.3Semi standard non polar33892256
Levuglandin E2,3TBDMS,isomer #6CCCCC[C@H](O)/C=C/C(=CO[Si](C)(C)C(C)(C)C)C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C3158.9Standard non polar33892256
Levuglandin E2,3TBDMS,isomer #6CCCCC[C@H](O)/C=C/C(=CO[Si](C)(C)C(C)(C)C)C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C3393.0Standard polar33892256
Levuglandin E2,3TBDMS,isomer #7C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(=CO[Si](C)(C)C(C)(C)C)/C=C/[C@@H](O)CCCCC3534.4Semi standard non polar33892256
Levuglandin E2,3TBDMS,isomer #7C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(=CO[Si](C)(C)C(C)(C)C)/C=C/[C@@H](O)CCCCC3131.5Standard non polar33892256
Levuglandin E2,3TBDMS,isomer #7C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(=CO[Si](C)(C)C(C)(C)C)/C=C/[C@@H](O)CCCCC3422.4Standard polar33892256
Levuglandin E2,4TBDMS,isomer #1CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C(C)(C)C)C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3850.0Semi standard non polar33892256
Levuglandin E2,4TBDMS,isomer #1CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C(C)(C)C)C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3270.0Standard non polar33892256
Levuglandin E2,4TBDMS,isomer #1CCCCC[C@@H](/C=C/C(=CO[Si](C)(C)C(C)(C)C)C(C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)=C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3149.9Standard polar33892256
Levuglandin E2,4TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(=CO[Si](C)(C)C(C)(C)C)/C=C/[C@H](CCCCC)O[Si](C)(C)C(C)(C)C3750.6Semi standard non polar33892256
Levuglandin E2,4TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(=CO[Si](C)(C)C(C)(C)C)/C=C/[C@H](CCCCC)O[Si](C)(C)C(C)(C)C3253.2Standard non polar33892256
Levuglandin E2,4TBDMS,isomer #2C=C(O[Si](C)(C)C(C)(C)C)[C@@H](C/C=C\CCCC(=O)O[Si](C)(C)C(C)(C)C)C(=CO[Si](C)(C)C(C)(C)C)/C=C/[C@H](CCCCC)O[Si](C)(C)C(C)(C)C3166.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Levuglandin E2 GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9263000000-296c4cb7515a1b701ad62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levuglandin E2 GC-MS (2 TMS) - 70eV, Positivesplash10-009x-9211700000-b71612e5c817a13ff0ec2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levuglandin E2 GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levuglandin E2 10V, Positive-QTOFsplash10-00kr-0019000000-126b7b23bc39fcdf32502017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levuglandin E2 20V, Positive-QTOFsplash10-00kr-4589000000-1ae21424ce78470e10f92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levuglandin E2 40V, Positive-QTOFsplash10-05mo-9351000000-c53c0dbb0d045d1c9b2c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levuglandin E2 10V, Negative-QTOFsplash10-0udi-0009000000-9ccba837b9402891d62b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levuglandin E2 20V, Negative-QTOFsplash10-0fsi-1927000000-5696407cfccd87b39eee2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levuglandin E2 40V, Negative-QTOFsplash10-0aou-9510000000-72d76c85a734ac0020762017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levuglandin E2 10V, Positive-QTOFsplash10-0ap0-0129000000-7e6a9daa4876d6b8223f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levuglandin E2 20V, Positive-QTOFsplash10-0avj-9365000000-1c01e58986a6aa66a04e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levuglandin E2 40V, Positive-QTOFsplash10-05r0-9410000000-e23687ff0d093af89b312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levuglandin E2 10V, Negative-QTOFsplash10-0ue9-0019000000-b418a2943f101d7191102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levuglandin E2 20V, Negative-QTOFsplash10-0uec-3459000000-fcf04b5aafdc13ca87cb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levuglandin E2 40V, Negative-QTOFsplash10-0abc-9641000000-6c6e011bd1ef9ed2b7172021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB022979
KNApSAcK IDNot Available
Chemspider ID30776554
KEGG Compound IDC13807
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLevuglandin
METLIN IDNot Available
PubChem Compound5282261
PDB IDNot Available
ChEBI ID34821
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceMiller, Donald B.; Raychaudhuri, Swadesh R.; Avasthi, Kamlakar; Lal, Kasturi; Levison, Bruce; Salomon, Robert G. Prostaglandin endoperoxides. 25 Levuglandin E2: enantiocontrolled total synthesis of a biologically active rearrangement product from the prostaglandin endoperoxide PGH2. J. Org. Chem. 1990(55) 3164-3175
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Salomon RG: Distinguishing levuglandins produced through the cyclooxygenase and isoprostane pathways. Chem Phys Lipids. 2005 Mar;134(1):1-20. Epub 2005 Jan 16. [PubMed:15752459 ]