Withanolide B (CHEM023638)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:12:00 UTC
Update Date2016-11-09 01:17:45 UTC
Accession NumberCHEM023638
Identification
Common NameWithanolide B
ClassSmall Molecule
DescriptionA Menatetrenone whose side-chain contains 4 isoprene units in an all-trans-configuration.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Methyl-3-(3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraenyl)-1,4-naphthoquinoneChEBI
2-Methyl-3-geranylgeranyl-1,4-naphthoquinoneChEBI
2-Methyl-3-trans-tetraprenyl-1,4-naphthoquinoneChEBI
Menaquinone 4ChEBI
Menaquinone K4ChEBI
Menaquinone-4ChEBI
MenatetrenonaChEBI
MenatetrenonumChEBI
MK-4ChEBI
MK4ChEBI
Vitamin K2ChEBI
Vitamin MK 4ChEBI
2-Methyl-3-all-trans-tetraprenyl-1,4-naphthoquinoneHMDB
Vitamin K2(20)HMDB
Kefton-2HMDB
(e,e,e)-Isomer OF menatetrenoneHMDB
Vitamin MK-4HMDB
MenaquinonesMeSH
Vitamin K quinoneMeSH
Vitamin K 2MeSH
MenaquinoneMeSH
Lycium substance bHMDB
Chemical FormulaC28H38O5
Average Molecular Mass454.598 g/mol
Monoisotopic Mass454.272 g/mol
CAS Registry Number56973-41-2
IUPAC Name15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁸]octadec-7-en-9-one
Traditional Name15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-5-hydroxy-10,14-dimethyl-3-oxapentacyclo[9.7.0.0²,⁴.0⁵,¹⁰.0¹⁴,¹⁸]octadec-7-en-9-one
SMILESCC(C1CCC2C3C4OC4C4(O)CC=CC(=O)C4(C)C3CCC12C)C1CC(C)=C(C)C(=O)O1
InChI IdentifierInChI=1S/C28H38O5/c1-14-13-20(32-25(30)15(14)2)16(3)17-8-9-18-22-19(10-12-26(17,18)4)27(5)21(29)7-6-11-28(27,31)24-23(22)33-24/h6-7,16-20,22-24,31H,8-13H2,1-5H3
InChI KeyZTEVDTFJUUJBLP-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as menaquinones. These are vitamin K2 compounds consisting of a naphtho-1,4-quinone ring system, which is substituted at the 2-position by an isoprenyl side-chain, and usually, at the 3-position by a methyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentMenaquinones
Alternative Parents
Substituents
  • Menaquinone
  • Diterpenoid
  • Naphthoquinone
  • Naphthalene
  • Aryl ketone
  • Quinone
  • Benzenoid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.004 g/LALOGPS
logP3.51ALOGPS
logP4.78ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)13.1ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.13 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity125.5 m³·mol⁻¹ChemAxon
Polarizability51.52 ųChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02br-3594800000-342201064ab3ced44f46Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03dr-7395750000-310dbfd34ec4e713cd0dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0005900000-688ecb047eeaf70aecd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-4019400000-c975545f7209b4f8488aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uy3-8439300000-f0185769a0d0164097ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0005900000-688ecb047eeaf70aecd1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-4019400000-c975545f7209b4f8488aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uy3-8439300000-f0185769a0d0164097ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001900000-88b2d268530467097752Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1002900000-fdadf8b6714187301cf8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-9104200000-bdd23549b698a72f5ac1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0001900000-88b2d268530467097752Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-1002900000-fdadf8b6714187301cf8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-9104200000-bdd23549b698a72f5ac1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0103900000-aef2673bbbbb0075640bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3215900000-dcd8d40fda1ce41a7f6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056s-3595500000-e4ba507f537b364f99b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000900000-c658cb9af4dd9a98de68Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0002900000-928ede65d5278775a412Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-7109800000-c966b2d9ad2935e3cb57Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB12148
HMDB IDHMDB0030017
FooDB IDFDB029792
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-9726
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMenatetrenone
Chemspider ID4445530
ChEBI ID78277
PubChem Compound ID5282367
Kegg Compound IDC00828
YMDB IDNot Available
ECMDB IDECMDB21552
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=22692649
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23169578
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23346882
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23702931
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23832575
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=24085302
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24138531
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=24342502
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=24426779
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=24489112
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24508562
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=24630057
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24737747
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24841104
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24975215
16. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
17. 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.
18. 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.
19. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
20. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
21. The lipid handbook with CD-ROM