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Capsianoside I (FDB002663)

Record Information
Version1.0
Creation date2010-04-08 22:05:28 UTC
Update date2019-11-26 02:57:47 UTC
Primary IDFDB002663
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCapsianoside I
DescriptionConstituent of Capsicum annuum variety fascuilatum Capsianosides are acyclic diterpene glycosides, water-soluble constituents present in the fruits of Paprika (Paprika Capsicum annuum L. variety grossum Bailey) and Jalapeno (Jalapeno Capsicum annuum L. variety annuum), that are used as vegetables and spices. Paprika is known for its high vitamin C content and has been isolated from Hungarian paprika in large amounts. Jalapeno is a stimulating spice which contains capsaicin and related compounds in its fruits and veins. (PMID: 17015971); The genus Capsicum (Solanaceae) includes many species widely cultivated in Asia, Africa, and Mediterranean countries. Peppers are native plants of America, and the fruits (pericarps) are consumed as vegetable foods, spices, and external medicines and are also a source of vitamins A, C, and E. Hot chili pepper has been used for centuries as a condiment to aid digestion. Traditionally, medical doctors advise ulcer patients not to consume spicy foods like pungent capsicum products, while naturopaths and herbalists have tended to use hot seasonings to relieve ulcers. Phytochemical investigations have been mainly focused on hot components of pepper species and qualitative and quantitative determinations of phenolic metabolites with antioxidant activities. (PMID: 17002415). Capsianoside I is found in many foods, some of which are italian sweet red pepper, pepper (c. annuum), yellow bell pepper, and herbs and spices.
CAS Number121924-04-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.47 g/LALOGPS
logP0.2ALOGPS
logP0.39ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)4.84ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count14ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area236.06 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity165.87 m³·mol⁻¹ChemAxon
Polarizability69.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC32H52O14
IUPAC name(2E,6E,10E)-14-{[4,5-dihydroxy-6-(hydroxymethyl)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-4-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,15-tetraenoic acid
InChI IdentifierInChI=1S/C32H52O14/c1-6-32(5,12-8-11-17(2)9-7-10-18(3)13-20(35)14-19(4)29(41)42)46-31-28(26(39)24(37)22(16-34)44-31)45-30-27(40)25(38)23(36)21(15-33)43-30/h6,10-11,14,20-28,30-31,33-40H,1,7-9,12-13,15-16H2,2-5H3,(H,41,42)/b17-11+,18-10+,19-14+
InChI KeyISQUNAAALVXWGI-DFTZOVBQSA-N
Isomeric SMILESC\C(CC\C=C(/C)CC(O)\C=C(/C)C(O)=O)=C/CCC(C)(OC1OC(CO)C(O)C(O)C1OC1OC(CO)C(O)C(O)C1O)C=C
Average Molecular Weight660.7469
Monoisotopic Molecular Weight660.335706372
Classification
Description Belongs to the class of organic compounds known as sophorolipids. These are glycolipids containing a sophorose moiety linked glycosidically to the hydroxyl group of a 17-hydroxy-C18 saturated fatty acid. The carboxyl group of the fatty acid can be linked to the 4'-hydroxyl of the second glucose to form a lactone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentSophorolipids
Alternative Parents
Substituents
  • Sophorolipid
  • Diterpene glycoside
  • Diterpenoid
  • Terpene glycoside
  • Long-chain fatty acid
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Fatty acid
  • Unsaturated fatty acid
  • Oxane
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Acetal
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Organic oxygen compound
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 58.17%; H 7.93%; O 33.90%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]23D -7.6 (c, 0.5 in MeOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCapsianoside I, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00ng-2415239000-e565073769a625e6973cSpectrum
Predicted GC-MSCapsianoside I, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_1_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_1_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_1_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_2_11, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_2_12, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_2_13, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_2_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSCapsianoside I, TMS_2_15, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02ud-1119807000-daababb19341e41a08482016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015i-3149701000-cf1291c325032365a01e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01p9-2696501000-6202366b957383c8a7ed2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05r9-3409738000-db0c468031d3fd669a782016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02dr-3819602000-2d0e5591d7581d47a3682016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000i-8829000000-9867896327b01fbfc1332016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fcc-0295022000-9f3e1e9ff140ab0344302021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0892000000-dc79a7583633726749932021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-2932040000-bfb6a2afae24c693e1542021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0000095000-7cb16a214dda9712ff7a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-2000090000-5f4b0092c5e52e53ea8f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f6t-8261890000-de037c45419b137838f02021-09-22View Spectrum
NMRNot Available
ChemSpider ID17216190
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID14610541
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02318
CRC / DFC (Dictionary of Food Compounds) IDCMX16-T:CMY79-T
EAFUS IDNot Available
Dr. Duke IDCAPSIANOSIDE-I
BIGG IDNot Available
KNApSAcK IDNot Available
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
angiotensin converting enzyme inhibitor35457 An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1).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).