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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:46:15 UTC
Update Date2019-07-23 06:19:26 UTC
HMDB IDHMDB0035750
Secondary Accession Numbers
  • HMDB35750
Metabolite Identification
Common NameZiziphin
DescriptionZiziphin belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Ziziphin is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862766
Synonyms
ValueSource
ZizyphinHMDB
4-(Acetyloxy)-2-{[7-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}-5-hydroxy-6-methyloxan-3-yl acetic acidGenerator
Chemical FormulaC51H80O18
Average Molecular Weight981.1701
Monoisotopic Molecular Weight980.534465756
IUPAC Name3-(acetyloxy)-2-{[7-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}-5-hydroxy-6-methyloxan-4-yl acetate
Traditional Name3-(acetyloxy)-2-{[7-({4,5-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}oxy)-2,6,6,10,16-pentamethyl-18-(2-methylprop-1-en-1-yl)-19,21-dioxahexacyclo[18.2.1.0¹,¹⁴.0²,¹¹.0⁵,¹⁰.0¹⁵,²⁰]tricosan-16-yl]oxy}-5-hydroxy-6-methyloxan-4-yl acetate
CAS Registry Number73667-51-3
SMILES
CC1OC(OC2C(O)C(O)COC2OC2CCC3(C)C(CCC4(C)C3CCC3C5C6(CC43CO6)OC(CC5(C)OC3OC(C)C(O)C(OC(C)=O)C3OC(C)=O)C=C(C)C)C2(C)C)C(O)C(O)C1O
InChI Identifier
InChI=1S/C51H80O18/c1-23(2)18-28-19-49(11,69-45-41(65-27(6)53)39(64-26(5)52)35(56)25(4)63-45)42-29-12-13-32-47(9)16-15-33(46(7,8)31(47)14-17-48(32,10)50(29)21-51(42,68-28)61-22-50)66-44-40(36(57)30(54)20-60-44)67-43-38(59)37(58)34(55)24(3)62-43/h18,24-25,28-45,54-59H,12-17,19-22H2,1-11H3
InChI KeyMHCWKKSYGWYURT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point213 - 215 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.045 g/LALOGPS
logP3.31ALOGPS
logP3.22ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)12.08ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area247.82 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity241.3 m³·mol⁻¹ChemAxon
Polarizability105.4 ųChemAxon
Number of Rings9ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ul9-3100314936-7c54fa3f006005d2c89fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ff0-9100718711-337c41d72ee0a756bdedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uk9-4400918401-b48489a2ee6b7f5bc5f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0159-9101000224-735e6b27f9ce5963a2fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0nmj-5700135924-650f600b16068f273816Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-9501102100-e69a52b790cebed5b909Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB014480
KNApSAcK IDC00003561
Chemspider IDNot Available
KEGG Compound IDC08991
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkZiziphin
METLIN IDNot Available
PubChem Compound131751861
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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.