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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:59:09 UTC
Update Date2021-09-14 15:15:54 UTC
HMDB IDHMDB0034191
Secondary Accession Numbers
  • HMDB34191
Metabolite Identification
Common NameWithaperuvin B
DescriptionWithaperuvin B belongs to the class of organic compounds known as withanolides and derivatives. These are C28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22, and 26 to form a lactone ring. Withaperuvin B is an extremely weak basic (essentially neutral) compound (based on its pKa). Withaperuvin is found in fruits. Withaperuvin is a constituent of Physalis peruviana (Cape gooseberry).
Structure
Data?1583187661
Synonyms
ValueSource
Withaperuvin BHMDB
Chemical FormulaC28H38O8
Average Molecular Weight502.604
Monoisotopic Molecular Weight502.256668184
IUPAC Name(6R)-6-[(1S)-1-hydroxy-1-[(1S,2R,6S,7S,8S,10R,14S,15S)-6,7,8,14-tetrahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-4,11-dien-14-yl]ethyl]-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one
Traditional Name(6R)-6-[(1S)-1-hydroxy-1-[(1S,2R,6S,7S,8S,10R,14S,15S)-6,7,8,14-tetrahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-4,11-dien-14-yl]ethyl]-3,4-dimethyl-5,6-dihydropyran-2-one
CAS Registry Number81644-35-1
SMILES
[H][C@@]1(CC(C)=C(C)C(=O)O1)[C@](C)(O)[C@]1(O)CC=C2[C@]3([H])C[C@H](O)[C@]4(O)[C@@H](O)C=CC(=O)[C@]4(C)[C@@]3([H])CC[C@]12C
InChI Identifier
InChI=1S/C28H38O8/c1-14-12-22(36-23(32)15(14)2)26(5,33)27(34)11-9-17-16-13-21(31)28(35)20(30)7-6-19(29)25(28,4)18(16)8-10-24(17,27)3/h6-7,9,16,18,20-22,30-31,33-35H,8,10-13H2,1-5H3/t16-,18-,20-,21-,22+,24-,25-,26-,27-,28+/m0/s1
InChI KeyIHIHXNCZVACPKN-WOONZQPCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentWithanolides and derivatives
Alternative Parents
Substituents
  • Withanolide-skeleton
  • 20-hydroxysteroid
  • 17-hydroxysteroid
  • Oxosteroid
  • 1-oxosteroid
  • Hydroxysteroid
  • 5-hydroxysteroid
  • 6-hydroxysteroid
  • 4-hydroxysteroid
  • Cyclohexenone
  • Dihydropyranone
  • Pyran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Cyclic alcohol
  • Secondary alcohol
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point269 - 270 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.04 g/LALOGPS
logP10(1.43) g/LALOGPS
logP10(1.29) g/LChemAxon
logS10(-3.1) g/LALOGPS
pKa (Strongest Acidic)12.17ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity132.53 m³·mol⁻¹ChemAxon
Polarizability53.64 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Withaperuvin B,1TMS,#1CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14138.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,1TMS,#2CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14152.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,1TMS,#3CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14124.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,1TMS,#4CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14080.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,1TMS,#5CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14102.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TMS,#1CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14091.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TMS,#2CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14035.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TMS,#3CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14010.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TMS,#4CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14033.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TMS,#5CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14061.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TMS,#6CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14040.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TMS,#7CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14061.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TMS,#8CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O[Si](C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14013.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TMS,#9CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14039.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,3TMS,#1CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C13974.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,3TMS,#2CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C13974.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,3TMS,#3CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C13998.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,3TMS,#4CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O[Si](C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C13942.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,3TMS,#5CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C13971.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,3TMS,#6CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C13974.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,3TMS,#7CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O[Si](C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C13969.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,3TMS,#8CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C13984.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,4TMS,#1CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O[Si](C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C13898.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,4TMS,#2CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C13916.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,1TBDMS,#1CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14370.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,1TBDMS,#2CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14378.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,1TBDMS,#3CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14334.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,1TBDMS,#4CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14299.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,1TBDMS,#5CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14322.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TBDMS,#1CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14552.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TBDMS,#2CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14487.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TBDMS,#3CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14458.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TBDMS,#4CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14495.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TBDMS,#5CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14503.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TBDMS,#6CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14470.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TBDMS,#7CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14512.1Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TBDMS,#8CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14436.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TBDMS,#9CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14460.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,3TBDMS,#1CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14640.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,3TBDMS,#2CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14630.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,3TBDMS,#3CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14675.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,3TBDMS,#4CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14598.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,3TBDMS,#5CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14623.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,3TBDMS,#6CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14631.2Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,3TBDMS,#7CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14593.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,3TBDMS,#8CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14612.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withaperuvin B,2TMS,#10CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14017.1Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Withaperuvin B,3TMS,#9CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C13993.1Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Withaperuvin B,3TMS,#10CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C13957.0Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Withaperuvin B,4TMS,#3CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C13940.1Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Withaperuvin B,4TMS,#4CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C13905.9Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Withaperuvin B,4TMS,#5CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C13918.0Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Withaperuvin B,5TMS,#1CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@]2(O[Si](C)(C)C)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C)[C@]5(O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C13864.2Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Withaperuvin B,2TBDMS,#10CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14448.6Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Withaperuvin B,3TBDMS,#9CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O[Si](C)(C)C(C)(C)C)CC=C3[C@@H]4C[C@H](O)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14630.9Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Withaperuvin B,3TBDMS,#10CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@]2(O)CC=C3[C@@H]4C[C@H](O[Si](C)(C)C(C)(C)C)[C@]5(O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]5(C)[C@H]4CC[C@@]32C)C14580.5Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Withaperuvin B GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Withaperuvin B GC-MS (TMS_3_9) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Withaperuvin B GC-MS (TMS_3_10) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Withaperuvin B GC-MS (TMS_4_3) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Withaperuvin B GC-MS (TMS_4_4) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Withaperuvin B GC-MS (TMS_4_5) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Withaperuvin B GC-MS (TMS_5_1) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Withaperuvin B GC-MS (TBDMS_2_10) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Withaperuvin B GC-MS (TBDMS_3_9) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Withaperuvin B GC-MS (TBDMS_3_10) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Withaperuvin B GC-MS ("Withaperuvin B,2TMS,#10" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withaperuvin B 10V, Negative-QTOFsplash10-0udi-0004290000-92a4ab8f1780bf9e3dca2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withaperuvin B 20V, Negative-QTOFsplash10-0a4i-0009010000-a3f01b1039da5edee3132021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withaperuvin B 40V, Negative-QTOFsplash10-0006-9304000000-8006b14fecfba613952f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withaperuvin B 10V, Positive-QTOFsplash10-0uxr-0302970000-5e409be2293b3a6ad67d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withaperuvin B 20V, Positive-QTOFsplash10-066r-7109600000-ac60e6a9db6af43a43822021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withaperuvin B 40V, Positive-QTOFsplash10-014i-2942000000-8c96536688011cd1d69a2021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012487
KNApSAcK IDC00058211
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.