Record Information
Version1.0
Creation date2010-04-08 22:11:57 UTC
Update date2018-05-29 01:20:30 UTC
Primary IDFDB015623
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name3-Dehydronobilin
DescriptionIsolated from Anthemis nobilis (Roman chamomile). 3-Dehydronobilin is found in roman camomile and herbs and spices.
CAS Number63529-14-6
Structure
Thumb
Synonyms
SynonymSource
6,10-Dimethyl-3-methylidene-2,9-dioxo-2H,3H,3ah,4H,5H,8H,9H,11ah-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoic acidGenerator
3-Dehydronobilindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP3.19ALOGPS
logP4.02ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)6.17ChemAxon
pKa (Strongest Basic)-5.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.67 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity96.04 m³·mol⁻¹ChemAxon
Polarizability35.76 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H24O5
IUPAC name6,10-dimethyl-3-methylidene-2,9-dioxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-2-methylbut-2-enoate
InChI IdentifierInChI=1S/C20H24O5/c1-6-12(3)19(22)24-16-9-11(2)7-8-15(21)13(4)10-17-18(16)14(5)20(23)25-17/h6-7,10,16-18H,5,8-9H2,1-4H3/b11-7+,12-6-,13-10+
InChI KeyFKDIIXZIKCNXAT-QLDBJWRKSA-N
Isomeric SMILESC\C=C(\C)C(=O)OC1C\C(C)=C\CC(=O)\C(C)=C\C2OC(=O)C(=C)C12
Average Molecular Weight344.4016
Monoisotopic Molecular Weight344.162373878
Classification
Description belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentGermacranolides and derivatives
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 69.75%; H 7.02%; O 23.23%DFC
Melting PointMp 205°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +136.6 (c, 0.526 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kai-9032000000-275d5fb73e9f5ca7a0f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3059000000-ddaab2f0dd2ef979b913View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0032-9152000000-2501bf40adf2334fad3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fsi-9210000000-16b49fceac282eb89e4cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1049000000-3c3fa14a3682f1071475View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0005-6096000000-a1b30547b95e9219cb08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001a-9430000000-9abec1ed0dd653fa3720View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36691
CRC / DFC (Dictionary of Food Compounds) IDKFB18-C:KFB53-J
EAFUS IDNot Available
Dr. Duke ID3-DEHYDRONOBILIN
BIGG IDNot Available
KNApSAcK IDC00011800
HET 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
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.