Record Information
Version1.0
Creation date2011-09-21 00:14:55 UTC
Update date2015-07-21 06:57:14 UTC
Primary IDFDB022496
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4a-Methylzymosterol
DescriptionProstaglandin E2, also known as dinoproston or PGE2, belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Thus, prostaglandin E2 is considered to be an eicosanoid lipid molecule. Prostaglandin E2 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
CAS Number7448-03-5
Structure
Thumb
Synonyms
SynonymSource
(15S)-Prostaglandin e2ChEBI
(5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acidChEBI
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoateChEBI
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoateChEBI
(e,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoic acidChEBI
(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic acidChEBI
DinoprostonChEBI
DinoprostonaChEBI
DinoprostoneChEBI
DinoprostonumChEBI
PGE2ChEBI
PrepidilChEBI
PropessChEBI
Prostin e2ChEBI
CervidilKegg
(5Z,11a,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-OateGenerator
(5Z,11a,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-Oic acidGenerator
(5Z,11alpha,13E,15S)-11,15-Dihydroxy-9-oxoprosta-5,13-dien-1-OateGenerator
(5Z,11Α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-OateGenerator
(5Z,11Α,13E,15S)-11,15-dihydroxy-9-oxoprosta-5,13-dien-1-Oic acidGenerator
(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoateGenerator
(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprost-13-enoic acidGenerator
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprost-13-enoic acidGenerator
(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoateGenerator
(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprost-13-enoic acidGenerator
(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprosta-5,13-dienoateGenerator
(5Z,13E)-(15S)-11a,15-Dihydroxy-9-oxoprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-11alpha,15-Dihydroxy-9-oxoprosta-5,13-dienoic acidGenerator
(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprosta-5,13-dienoateGenerator
(5Z,13E)-(15S)-11Α,15-dihydroxy-9-oxoprosta-5,13-dienoic acidGenerator
(e,Z)-(1R,2R,3R)-7-(3-Hydroxy-2-((3S)-(3-hydroxy-1-octenyl))-5-oxocyclopentyl)-5-heptenoateGenerator
(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((S,e)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoateGenerator
(-)-Prostaglandin e2HMDB
(5Z,13E,15S)-11-alpha,15-Dihydroxy-9-oxoprost-5,13-dienoateHMDB
(5Z,13E,15S)-11-alpha,15-Dihydroxy-9-oxoprost-5,13-dienoic acidHMDB
5-trans-PGE2HMDB
GlandinHMDB
L-Prostaglandin e2HMDB
Minprositin e2HMDB
Minprostin e2HMDB
Prostaglandin eHMDB
Prostaglandin e2alphaHMDB
Prostarmon eHMDB
ProstinHMDB
e2, ProstaglandinHMDB
Prepidil gelHMDB
alpha, Prostaglandin e2HMDB
e2 alpha, ProstaglandinHMDB
e2alpha, ProstaglandinHMDB
alpha, PGE2HMDB
ProstenonHMDB
Gel, prepidilHMDB
PGE2 alphaHMDB
PGE2alphaHMDB
Prostaglandin e2 alphaHMDB
(3beta,4alpha,5alpha)-4-Methylcholesta-8,24-dien-3-olChEBI
4alpha-Methyl-5alpha-cholesta-8,24-dien-3beta-olChEBI
(3b,4a,5a)-4-Methylcholesta-8,24-dien-3-olGenerator
(3β,4α,5α)-4-methylcholesta-8,24-dien-3-olGenerator
4a-Methyl-5a-cholesta-8,24-dien-3b-olGenerator
4α-methyl-5α-cholesta-8,24-dien-3β-olGenerator
(4S,5S)-4,10,13-Trimethyl-17-(6-methylhept-5-en-2-yl)-2,3,4,5,6,7,11,12,14, 15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-olHMDB
4alpha-MethylzymosterolHMDB
(3b,4a,5a)-4-methylcholesta-8,24-dien-3-olhmdb
(3beta,4alpha,5alpha)-4-methylcholesta-8,24-dien-3-olhmdb
(4S,5S)-4,10,13-trimethyl-17-(6-methylhept-5-en-2-yl)-2,3,4,5,6,7,11,12,14, 15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-olhmdb
4a-methyl-5a-cholesta-8,24-dien-3b-olhmdb
4a-Methylzymosterolhmdb
4alpha-methyl-5alpha-cholesta-8,24-dien-3beta-olhmdb
4α-methylzymosterolGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.0007 g/LALOGPS
logP6.52ALOGPS
logP7.03ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)18.96ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity125.67 m³·mol⁻¹ChemAxon
Polarizability51.58 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H46O
IUPAC name(2S,5S,6S,7S,11R,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
InChI IdentifierInChI=1S/C28H46O/c1-18(2)8-7-9-19(3)22-12-13-24-21-10-11-23-20(4)26(29)15-17-28(23,6)25(21)14-16-27(22,24)5/h8,19-20,22-24,26,29H,7,9-17H2,1-6H3/t19-,20+,22-,23+,24+,26+,27-,28+/m1/s1
InChI KeyFOUJWBXBKVVHCJ-YIJYGBTNSA-N
Isomeric SMILES[H][C@@]1(CC[C@@]2([H])C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC=C(C)C
Average Molecular Weight398.6642
Monoisotopic Molecular Weight398.354866094
Classification
Description belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Cyclopentanol
  • Fatty acid
  • Unsaturated fatty acid
  • Cyclic alcohol
  • Ketone
  • Cyclic ketone
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02ar-0019000000-da364020d6f55a8d1836JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4l-3004900000-86ae2efd8b737e675270JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001j-0009000000-f485cbb263f2f4b1b84aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01sj-2129000000-22c00d60920d1e5a4fabJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-3459000000-7d25553141c326b6521eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-da18f5394671385950baJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-dbaa936472d9a3662d91JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0159-1009000000-dcd434b2beb43e39f10bJSpectraViewer
ChemSpider ID20036827
ChEMBL IDNot Available
KEGG Compound IDC05103
Pubchem Compound ID22212495
Pubchem Substance IDNot Available
ChEBI ID1949
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01217
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Steroid BiosynthesisSMP00023 map00100
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference