You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:51:28 UTC
Update Date2019-07-23 06:11:39 UTC
HMDB IDHMDB0032732
Secondary Accession Numbers
  • HMDB32732
Metabolite Identification
Common Namecis-Solamin
Descriptioncis-Solamin belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. cis-Solamin is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1563862299
Synonyms
ValueSource
cis-SolaminMeSH
Chemical FormulaC35H64O5
Average Molecular Weight564.8797
Monoisotopic Molecular Weight564.475375158
IUPAC Name3-{13-hydroxy-13-[5-(1-hydroxytridecyl)oxolan-2-yl]tridecyl}-5-methyl-2,5-dihydrofuran-2-one
Traditional Name3-{13-hydroxy-13-[5-(1-hydroxytridecyl)oxolan-2-yl]tridecyl}-5-methyl-5H-furan-2-one
CAS Registry Number158705-59-0
SMILES
CCCCCCCCCCCCC(O)C1CCC(O1)C(O)CCCCCCCCCCCCC1=CC(C)OC1=O
InChI Identifier
InChI=1S/C35H64O5/c1-3-4-5-6-7-8-12-15-18-21-24-31(36)33-26-27-34(40-33)32(37)25-22-19-16-13-10-9-11-14-17-20-23-30-28-29(2)39-35(30)38/h28-29,31-34,36-37H,3-27H2,1-2H3
InChI KeyRBSBTRALZZSVBA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty alcohols
Direct ParentAnnonaceous acetogenins
Alternative Parents
Substituents
  • Annonaceae acetogenin skeleton
  • Long chain fatty alcohol
  • 2-furanone
  • Dihydrofuran
  • Tetrahydrofuran
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Secondary alcohol
  • Lactone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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 Point63 - 66 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
logP8.95ALOGPS
logP10.48ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)13.87ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity166 m³·mol⁻¹ChemAxon
Polarizability73.22 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00r5-3294210000-7f2b9bc47eb9ece5b040Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00r6-5029012000-c7377329e71e76aa3f1fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0120190000-4df70c69864be33785fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-1951230000-6d71225fb6e618f40d9fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-4920100000-a2e2c939d0f6eaf78feeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000090000-14eb295be351f2727e99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02ta-1373090000-78015407416bde782802Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-2293100000-17a0d359516f1f70ef2fSpectrum
Biological Properties
Cellular Locations
  • 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 IDFDB020763
KNApSAcK IDNot Available
Chemspider ID8274978
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10099444
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. Kojima N, Hayashi H, Suzuki S, Tominaga H, Maezaki N, Tanaka T, Yamori T: Synthesis of C4-fluorinated solamins and their growth inhibitory activity against human cancer cell lines. Bioorg Med Chem Lett. 2008 Dec 15;18(24):6451-3. doi: 10.1016/j.bmcl.2008.10.069. Epub 2008 Oct 19. [PubMed:18993063 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.