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Showing Compound Theasaponin A3 (FDB001829)

Record Information
Version1.0
Creation date2010-04-08 22:05:07 UTC
Update date2019-11-26 02:56:41 UTC
Primary IDFDB001829
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTheasaponin A3
Description(2S,3S,4S,5R)-6-{[(3S,4R,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8,9-bis(acetyloxy)-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4-{[(2S,4S,5S)-4,5-dihydroxy-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. Based on a literature review very few articles have been published on (2S,3S,4S,5R)-6-{[(3S,4R,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8,9-bis(acetyloxy)-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4-{[(2S,4S,5S)-4,5-dihydroxy-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid.
CAS Number878049-12-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.69 g/LALOGPS
logP1.07ALOGPS
logP-0.95ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.27ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count25ChemAxon
Hydrogen Donor Count13ChemAxon
Polar Surface Area432.8 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity299.42 m³·mol⁻¹ChemAxon
Polarizability131.71 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC61H94O28
IUPAC name(2S,3S,4S,5R)-6-{[(3S,4R,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8,9-bis(acetyloxy)-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-{[(2Z)-2-methylbut-2-enoyl]oxy}-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-yl]oxy}-4-{[(2S,4S,5S)-4,5-dihydroxy-3-{[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-3-hydroxy-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-2-carboxylic acid
InChI IdentifierInChI=1S/C61H94O28/c1-11-25(2)51(78)89-48-49(82-27(4)66)61(24-64)29(18-56(48,5)6)28-12-13-34-57(7)16-15-35(58(8,23-63)33(57)14-17-59(34,9)60(28,10)19-36(61)81-26(3)65)84-55-47(88-53-42(74)40(72)39(71)32(20-62)83-53)44(43(75)45(86-55)50(76)77)85-54-46(38(70)31(68)22-80-54)87-52-41(73)37(69)30(67)21-79-52/h11-12,29-49,52-55,62-64,67-75H,13-24H2,1-10H3,(H,76,77)/b25-11-/t29-,30+,31-,32+,33+,34+,35-,36+,37-,38-,39-,40-,41+,42+,43-,44-,45-,46?,47+,48-,49-,52-,53-,54-,55?,57-,58-,59+,60+,61-/m0/s1
InChI KeyYFRAVWSJUOHVQT-PKLVKLGCSA-N
Isomeric SMILESOC[C@H]1O[C@@H](O[C@H]2C(O[C@H]3CC[C@@]4(C)[C@@]([H])(CC[C@]5(C)[C@]4([H])CC=C4[C@]6([H])CC(C)(C)[C@@H](OC(=O)C(\C)=C/C)[C@H](OC(=O)C)[C@]6(CO)[C@H](OC(=O)C)C[C@@]54C)[C@]3(C)CO)O[C@H](C(=O)O)[C@@H](O)[C@@H]2O[C@@H]2OC[C@H](O)[C@H](O)C2O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@H]1O
Average Molecular Weight1275.3823
Monoisotopic Molecular Weight1274.593162424
Classification
Description Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTriterpene saponins
Alternative Parents
Substituents
  • Triterpene saponin
  • Triterpenoid
  • Oligosaccharide
  • 16-oxosteroid
  • Oxosteroid
  • Steroid
  • Fatty acyl glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Tetracarboxylic acid or derivatives
  • Glucuronic acid or derivatives
  • Glycosyl compound
  • O-glycosyl compound
  • Beta-hydroxy acid
  • Fatty acid ester
  • Fatty acyl
  • Pyran
  • Oxane
  • Hydroxy acid
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Acetal
  • Alcohol
  • Primary alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-7690008014-359805f7fc3bd661a7592016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adj-6310009025-3ec3a86ef8211c9576d62016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00aj-9510006034-1c098275b70a9a08a16a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05fs-5890002000-d6ace58a1726b3ed544e2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05c5-3940002001-bcec41b3ef6854bb215f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-7900003001-b9c279f29d06d9d1e2432016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0690000000-3d08a79f6154066447432021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056u-6970011103-efd3bb69b855298ab86a2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-5892802121-159f199c0755e937d6172021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-5290000000-2c9aa81c3c46620b02002021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-95ad1423871c1a235c1d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9210000001-3ae147371c0139636e862021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI ID168591
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00032323
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.