Showing Compound Card for lsoprene (CDB000629)

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Record Information
Version1.0
Created at2020-03-19 00:47:34 UTC
Updated at2020-11-18 16:35:21 UTC
CannabisDB IDCDB000629
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namelsoprene
DescriptionIsoprene, also known as 2-methyl-1,3-butadiene, belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch. It is a common organic compound with the formula CH2=C(CH3)‚àíCH=CH2. In its pure form it is a colorless volatile liquid. It is produced by many plants and animals (including humans) and its polymers are the main component of natural rubber. C. G. Williams named the compound in 1860 after obtaining it from thermal decomposition (pyrolysis) of natural rubber. He correctly deduced the empirical formula C5H8 ( Ref:DOI ). Isoprene is produced and emitted by many species of trees (major producers are oaks, poplars, eucalyptus, and some legumes). Isoprene is made through the mevalonic acid pathway in the cytosol and also, in eubacteria, green algae and the plastids of superior plants, through the methyl-erythritol 4-phosphate pathway (MEP pathway, also called the non-mevalonate pathway). Isoprene has been detected, but not quantified, in a few different foods, such as carrots, sweet oranges, and wild carrots. Isoprene has also been detected as a volatile component of cannabis samples (PMID: 26657499 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Methyl-1,3-butadieneChEBI
2-MethylbutadieneChEBI
2-MethyldivinylChEBI
beta-MethylbivinylChEBI
CH2=C(CH3)CH=ch2ChEBI
IsopentadieneChEBI
IsoprenChEBI
IsoprenoChEBI
IsoterpeneChEBI
b-MethylbivinylGenerator
Β-methylbivinylGenerator
Chemical FormulaC5H8
Average Molecular Weight68.12
Monoisotopic Molecular Weight68.0626
IUPAC Name2-methylbuta-1,3-diene
Traditional Nameisoprene
CAS Registry Number68441-58-7
SMILES
CC(=C)C=C
InChI Identifier
InChI=1S/C5H8/c1-4-5(2)3/h4H,1-2H2,3H3
InChI KeyRRHGJUQNOFWUDK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassUnsaturated hydrocarbons
Sub ClassBranched unsaturated hydrocarbons
Direct ParentBranched unsaturated hydrocarbons
Alternative Parents
Substituents
  • Branched unsaturated hydrocarbon
  • Alkadiene
  • Unsaturated aliphatic hydrocarbon
  • Olefin
  • Acyclic olefin
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.22ALOGPS
logP1.88ChemAxon
logS-1.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity24.58 m³·mol⁻¹ChemAxon
Polarizability8.58 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-014i-9000000000-bcc7aa57f0fa0fd9d3992014-09-20View Spectrum
Predicted GC-MSlsoprene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSlsoprene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-aa7bf6693faf53f2c9f82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9000000000-79f5e8913a6e3948a9252016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-cc71ad3e01e005b392f42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-c4e0cc5173528ae70b452016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-748a9309c1a76a36f5822016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uxr-9000000000-b24db55f64156fae0d1d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-13c3d4b2254b96312f2f2021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-9000000000-182e8f0f63d0901250e72021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-9000000000-7b7c61918e48120c38a52021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-9000000000-87c1aff470916cc072392021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9000000000-87c1aff470916cc072392021-10-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0gb9-9000000000-7033f85bf44b5b1856d12021-10-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0253673
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005121
KNApSAcK IDC00046784
Chemspider ID6309
KEGG Compound IDC16521
BioCyc IDCPD-9436
BiGG IDNot Available
Wikipedia LinkIsoprene
METLIN IDNot Available
PubChem Compound6557
PDB IDNot Available
ChEBI ID35194
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]