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Showing Compound Niveusin C (FDB012884)

Record Information
Version1.0
Creation date2010-04-08 22:10:25 UTC
Update date2019-11-26 03:07:47 UTC
Primary IDFDB012884
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNiveusin C
DescriptionNiveusin C, also known as annuithrin, belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Niveusin C is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number75680-27-2
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
AnnuithrinHMDB
(1S,2Z,4S,8R,9R,11R,12S)-1,12-Dihydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradec-2-en-9-yl (2Z)-2-methylbut-2-enoic acidGenerator
Niveusin Cdb_source
Predicted Properties
PropertyValueSource
Water Solubility1.52 g/LALOGPS
logP1.21ALOGPS
logP2.43ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)6.21ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area102.29 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity96.59 m³·mol⁻¹ChemAxon
Polarizability39.05 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC20H26O7
IUPAC name(1R,2Z,4S,8R,9R,11R,12S)-1,12-dihydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradec-2-en-9-yl (2Z)-2-methylbut-2-enoate
InChI IdentifierInChI=1S/C20H26O7/c1-6-10(2)17(22)26-14-8-19(5)15(21)9-20(24,27-19)11(3)7-13-16(14)12(4)18(23)25-13/h6-7,13-16,21,24H,4,8-9H2,1-3,5H3/b10-6-,11-7-/t13-,14+,15-,16-,19+,20-/m0/s1
InChI KeyWGVJNQGTZSPMCY-GEYOPIBESA-N
Isomeric SMILESC\C=C(\C)C(=O)O[C@@H]1C[C@@]2(C)O[C@](O)(C[C@@H]2O)\C(C)=C/[C@@H]2OC(=O)C(=C)[C@H]12
Average Molecular Weight378.4162
Monoisotopic Molecular Weight378.167853186
Classification
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic 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
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 63.48%; H 6.92%; O 29.60%DFC
Melting PointMp 125-126°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -148 (c, 0.28 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNiveusin C, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-06sl-9005000000-dba6851e52631c1d12feSpectrum
Predicted GC-MSNiveusin C, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0a59-9100310000-3dcf62b02f82dd0755b4Spectrum
Predicted GC-MSNiveusin C, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-3029000000-8a3702953c54978ea92b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-057i-9074000000-6f28250943839bc7f2582017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9030000000-7f719c01573e08f6bcc72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0019000000-ff1348c903a57f23491d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057j-6029000000-5f1109e65787704de5832017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ziv-5090000000-078e2e0c39aff2008caa2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004j-1093000000-a45f35179b06ec2311f72021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-6090000000-c380272ec11412d010492021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002b-4090000000-ebcb3d86340880c806902021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-4aeee19b2d437cda102f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06vi-0091000000-e0387beaa172d1a1341b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-7091000000-f1c31490e49ce1f071562021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09517
Pubchem Compound ID5320177
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB34474
CRC / DFC (Dictionary of Food Compounds) IDHNB88-U:HNC02-V
EAFUS IDNot Available
Dr. Duke IDNIVEUSIN-C|ANNUITHRIN
BIGG IDNot Available
KNApSAcK IDC00003338
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 septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
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
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Nobuo Ohno and Tom J. Mabry, “Sesquiterpene lactones and diterpene carboxylic acids in Helianthus niveus subspecies Canescens,” Phytochemistry 19, no. 4 (1980): 609-614. [No PubMed ID] PDF [Isolation]
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.