Record Information
Version1.0
Creation date2010-04-08 22:11:19 UTC
Update date2019-11-26 03:10:15 UTC
Primary IDFDB014514
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNomilin
DescriptionNomilin belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. Nomilin is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number1063-77-0
Structure
Thumb
Synonyms
SynonymSource
1-(Acetyloxy)-1,2-dihydroobacunoic acid .epislon.-lactoneHMDB
1-(Acetyloxy)-1,2-dihydroobacunoic acid eta-lactoneHMDB
Obacunoic acid, 1-(acetyloxy)-1,2-dihydro-, eta-lactoneHMDB
7-(Furan-3-yl)-1,8,12,17,17-pentamethyl-5,15,20-trioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-13-yl acetic acidGenerator
NomilinMeSH
Predicted Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP3.59ALOGPS
logP3.02ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)17.84ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area121.64 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity125.61 m³·mol⁻¹ChemAxon
Polarizability52.45 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC28H34O9
IUPAC name7-(furan-3-yl)-1,8,12,17,17-pentamethyl-5,15,20-trioxo-3,6,16-trioxapentacyclo[9.9.0.0²,⁴.0²,⁸.0¹²,¹⁸]icosan-13-yl acetate
InChI IdentifierInChI=1S/C28H34O9/c1-14(29)34-19-12-20(31)36-24(2,3)17-11-18(30)27(6)16(26(17,19)5)7-9-25(4)21(15-8-10-33-13-15)35-23(32)22-28(25,27)37-22/h8,10,13,16-17,19,21-22H,7,9,11-12H2,1-6H3
InChI KeyKPDOJFFZKAUIOE-UHFFFAOYSA-N
Isomeric SMILESCC(=O)OC1CC(=O)OC(C)(C)C2CC(=O)C3(C)C(CCC4(C)C(OC(=O)C5OC345)C3=COC=C3)C12C
Average Molecular Weight514.5642
Monoisotopic Molecular Weight514.220282686
Classification
Description belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentLimonoids
Alternative Parents
Substituents
  • Limonoid skeleton
  • Naphthopyran
  • Naphthalene
  • Tricarboxylic acid or derivatives
  • Caprolactone
  • 1,4-dioxepane
  • Delta valerolactone
  • Dioxepane
  • Oxepane
  • Delta_valerolactone
  • Pyran
  • Oxane
  • Heteroaromatic compound
  • Furan
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Organoheterocyclic compound
  • Ether
  • Oxirane
  • Oxacycle
  • Dialkyl ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
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 stateNot Available
Physical DescriptionNot Available
Mass CompositionC 65.36%; H 6.66%; O 27.98%DFC
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, Positivesplash10-075c-4042900000-fc535c0f11729f4239e0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0000940000-e3c7abba890a6b92fd3aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ac9-1005900000-c2ec1f5596e3673813d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9214300000-ac3dee9f3fded529d9f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-02t9-1000930000-45a049d6ce0b3536f997JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0mxs-2000910000-3108b08c8b322c3f15c9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-9004500000-4830d9a5ba4d4894b690JSpectraViewer
ChemSpider ID288878
ChEMBL IDNot Available
KEGG Compound IDC08773
Pubchem Compound ID326240
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35772
CRC / DFC (Dictionary of Food Compounds) IDJRM82-P:JRM84-R
EAFUS IDNot Available
Dr. Duke IDNOMILIN
BIGG IDNot Available
KNApSAcK IDC00003722
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 / Bioactivities
DescriptorIDDefinitionReference
anti feedantDUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).