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Record Information
Version2.0
Created at2022-04-27 23:02:10 UTC
Updated at2022-04-27 23:02:10 UTC
NP-MRD IDNP0051811
Secondary Accession NumbersNone
Natural Product Identification
Common NameJuvenile hormone III
DescriptionJuvenile hormone III, also known as JH III, belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. Thus, juvenile hormone III is considered to be an isoprenoid lipid molecule. Juvenile hormone III is found in Apis cerana, Cyperus iria and Lettowianthus stellatus. Juvenile hormone III was first documented in 2012 (PMID: 22664054). Juvenile hormone III is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 23034815) (PMID: 23121109) (PMID: 24657668).
Structure
Thumb
Synonyms
ValueSource
(+)-Juvenile hormone IIIChEBI
(10R)-Juvenile hormone IIIChEBI
JH IIIChEBI
Juvenile hormone 3ChEBI
Methyl (2E,6E)-(10R)-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadienoateChEBI
Methyl (R-(e,e))-9-(3,3-dimethyloxiranyl)-3,7-dimethyl-2,6-nonadienoateChEBI
Methyl 10,11-epoxy-3,7,11-trimethyl-trans,trans-(10R)-2,6-dodecadienoateChEBI
Methyl 10,11-epoxy-3,7,11-trimethyl-trans,trans-2,6-dodecadienoateChEBI
Methyl R-(+)-10,11-epoxyfarnesateChEBI
Methyl (2E,6E)-(10R)-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadienoic acidGenerator
Methyl (R-(e,e))-9-(3,3-dimethyloxiranyl)-3,7-dimethyl-2,6-nonadienoic acidGenerator
Methyl 10,11-epoxy-3,7,11-trimethyl-trans,trans-(10R)-2,6-dodecadienoic acidGenerator
Methyl 10,11-epoxy-3,7,11-trimethyl-trans,trans-2,6-dodecadienoic acidGenerator
Methyl R-(+)-10,11-epoxyfarnesic acidGenerator
10,11-Epoxyfarnesenic acid methyl esterMeSH
Juvenile hormone III, (e,e)-(+-)-isomerMeSH
Juvenile hormone III, (e,e)-isomerMeSH
Juvenile hormone III, (R-(e,e))-isomerMeSH
Juvenile hormone III, (Z,e)-isomerMeSH
Methyl 10,11-epoxy-3,7,11-trimethyl-2,6-dodecanoateMeSH
Juvenile hormone III, (S-(e,e))-isomerMeSH
Chemical FormulaC16H26O3
Average Mass266.3758 Da
Monoisotopic Mass266.18819 Da
IUPAC Namemethyl (2E,6E)-9-[(2R)-3,3-dimethyloxiran-2-yl]-3,7-dimethylnona-2,6-dienoate
Traditional NameJH III
CAS Registry NumberNot Available
SMILES
COC(=O)\C=C(/C)CC\C=C(/C)CC[C@H]1OC1(C)C
InChI Identifier
InChI=1S/C16H26O3/c1-12(9-10-14-16(3,4)19-14)7-6-8-13(2)11-15(17)18-5/h7,11,14H,6,8-10H2,1-5H3/b12-7+,13-11+/t14-/m1/s1
InChI KeyQVJMXSGZTCGLHZ-HONBPKQLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Apis ceranaLOTUS Database
Cyperus iriaPlant
Lettowianthus stellatusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMonocyclic monoterpenoids
Alternative Parents
Substituents
  • Monocyclic monoterpenoid
  • Fatty acid ester
  • Fatty acyl
  • Methyl ester
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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
logP5.04ALOGPS
logP3.88ChemAxon
logS-4.1ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.53 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity78.46 m³·mol⁻¹ChemAxon
Polarizability31.95 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00003157
Chemspider IDNot Available
KEGG Compound IDC09694
BioCyc IDCPD-8838
BiGG IDNot Available
Wikipedia LinkJuvenile hormone
METLIN IDNot Available
PubChem Compound5281523
PDB IDNot Available
ChEBI ID27493
Good Scents IDNot Available
References
General References
  1. Ares AM, Nozal MJ, Bernal JL, Martin-Hernandez R, M Higes, Bernal J: Liquid chromatography coupled to ion trap-tandem mass spectrometry to evaluate juvenile hormone III levels in bee hemolymph from Nosema spp. infected colonies. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Jun 15;899:146-53. doi: 10.1016/j.jchromb.2012.05.016. Epub 2012 May 19. [PubMed:22664054 ]
  2. Paes-De-Oliveira VT, Berger B, Poiani SB, Paulino Simoes ZL, Da Cruz-Landim C: Effects of treatment of the fat body trophocytes of Melipona quadrifasciata anthidioides nurse workers and virgin queens in culture by juvenile hormone III and ecdysterone (20-HE). Microsc Res Tech. 2013 Jan;76(1):20-7. doi: 10.1002/jemt.22130. Epub 2012 Oct 4. [PubMed:23034815 ]
  3. Sim C, Denlinger DL: Juvenile hormone III suppresses forkhead of transcription factor in the fat body and reduces fat accumulation in the diapausing mosquito, Culex pipiens. Insect Mol Biol. 2013 Feb;22(1):1-11. doi: 10.1111/j.1365-2583.2012.01166.x. Epub 2012 Nov 4. [PubMed:23121109 ]
  4. Van Ekert E, Heylen K, Rouge P, Powell CA, Shatters RG Jr, Smagghe G, Borovsky D: Aedes aegypti juvenile hormone acid methyl transferase, the ultimate enzyme in the biosynthetic pathway of juvenile hormone III, exhibits substrate control. J Insect Physiol. 2014 May;64:62-73. doi: 10.1016/j.jinsphys.2014.03.001. Epub 2014 Mar 20. [PubMed:24657668 ]