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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:31:51 UTC
Update Date2022-03-07 02:53:51 UTC
HMDB IDHMDB0033769
Secondary Accession Numbers
  • HMDB33769
Metabolite Identification
Common NameRockogenin
DescriptionHalofuginone, also known as stenorol or C16H17BRCLN3O3, belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring. Halofuginone is a very strong basic compound (based on its pKa). Poultry feed additive for prevention of coccidiosis. ; Halofuginone, a fully synthetic small molecule, is a potent and selective regulator of stromal cell activation, cell migration and Collagen type I synthesis, a process that has been identified as a 'master switch' in the body's tissue repair process.
Structure
Data?1563862457
Synonyms
ValueSource
7-Bromo-6-chloro-3-[3-(3-hydroxy-2-piperidinyl)-2-oxopropyl]-4(3H)-quinazolinone, 9ciHMDB
C16H17BRCLN3O3HMDB
HalofuginonaHMDB
HalofuginonumHMDB
7-Bromo-6-chlorofebrifugineHMDB
StenorolHMDB
HalofunginoneHMDB
(3beta,5alpha,12beta,25R)-Spirostan-3,12-diolHMDB
5alpha,25alpha-Spirostan-3beta,12-diolHMDB
RocogeninHMDB
Chemical FormulaC27H44O4
Average Molecular Weight432.6359
Monoisotopic Molecular Weight432.323959896
IUPAC Name5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol
Traditional Name5,7',9',13'-tetramethyl-5'-oxaspiro[oxane-2,6'-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-10',16'-diol
CAS Registry Number16653-52-4
SMILES
CC1C2C(CC3C4CCC5CC(O)CCC5(C)C4CC(O)C23C)OC11CCC(C)CO1
InChI Identifier
InChI=1S/C27H44O4/c1-15-7-10-27(30-14-15)16(2)24-22(31-27)12-21-19-6-5-17-11-18(28)8-9-25(17,3)20(19)13-23(29)26(21,24)4/h15-24,28-29H,5-14H2,1-4H3
InChI KeyBQNMOLSYHYSCMS-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentQuinazolines
Alternative Parents
Substituents
  • Quinazoline
  • Pyrimidone
  • Aryl bromide
  • Aryl chloride
  • Aryl halide
  • Beta-aminoketone
  • Benzenoid
  • Pyrimidine
  • Piperidine
  • Heteroaromatic compound
  • 1,2-aminoalcohol
  • Ketone
  • Lactam
  • Secondary alcohol
  • Secondary aliphatic amine
  • Azacycle
  • Secondary amine
  • Organobromide
  • Organohalogen compound
  • Amine
  • Alcohol
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point218 - 220 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0026 g/LALOGPS
logP3.49ALOGPS
logP4.1ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)14.68ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.92 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity120.93 m³·mol⁻¹ChemAxon
Polarizability51.73 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+200.5231661259
DarkChem[M-H]-194.5631661259
DeepCCS[M-2H]-240.47830932474
DeepCCS[M+Na]+216.28830932474
AllCCS[M+H]+211.532859911
AllCCS[M+H-H2O]+209.532859911
AllCCS[M+NH4]+213.332859911
AllCCS[M+Na]+213.832859911
AllCCS[M-H]-207.232859911
AllCCS[M+Na-2H]-209.032859911
AllCCS[M+HCOO]-211.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RockogeninCC1C2C(CC3C4CCC5CC(O)CCC5(C)C4CC(O)C23C)OC11CCC(C)CO12893.4Standard polar33892256
RockogeninCC1C2C(CC3C4CCC5CC(O)CCC5(C)C4CC(O)C23C)OC11CCC(C)CO13257.1Standard non polar33892256
RockogeninCC1C2C(CC3C4CCC5CC(O)CCC5(C)C4CC(O)C23C)OC11CCC(C)CO13594.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Rockogenin,1TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CCC5CC(O[Si](C)(C)C)CCC5(C)C4CC(O)C3(C)C1C2C3524.4Semi standard non polar33892256
Rockogenin,1TMS,isomer #2CC1CCC2(OC1)OC1CC3C4CCC5CC(O)CCC5(C)C4CC(O[Si](C)(C)C)C3(C)C1C2C3510.3Semi standard non polar33892256
Rockogenin,2TMS,isomer #1CC1CCC2(OC1)OC1CC3C4CCC5CC(O[Si](C)(C)C)CCC5(C)C4CC(O[Si](C)(C)C)C3(C)C1C2C3474.0Semi standard non polar33892256
Rockogenin,1TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CCC5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CC(O)C3(C)C1C2C3750.4Semi standard non polar33892256
Rockogenin,1TBDMS,isomer #2CC1CCC2(OC1)OC1CC3C4CCC5CC(O)CCC5(C)C4CC(O[Si](C)(C)C(C)(C)C)C3(C)C1C2C3740.6Semi standard non polar33892256
Rockogenin,2TBDMS,isomer #1CC1CCC2(OC1)OC1CC3C4CCC5CC(O[Si](C)(C)C(C)(C)C)CCC5(C)C4CC(O[Si](C)(C)C(C)(C)C)C3(C)C1C2C3955.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Rockogenin GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-1549700000-a518737970031faa7b752017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rockogenin GC-MS (2 TMS) - 70eV, Positivesplash10-03di-4311690000-62b4b4a21ad4ac20d1282017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Rockogenin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 10V, Positive-QTOFsplash10-014i-3025900000-24e394e51aa633bb3e222015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 20V, Positive-QTOFsplash10-00xr-4093300000-c0056049ab2eb838b92c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 40V, Positive-QTOFsplash10-0ldi-9026000000-c32913c5e74b4d7e4b502015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 10V, Positive-QTOFsplash10-014i-3025900000-24e394e51aa633bb3e222015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 20V, Positive-QTOFsplash10-00xr-4093300000-c0056049ab2eb838b92c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 40V, Positive-QTOFsplash10-0ldi-9026000000-c32913c5e74b4d7e4b502015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 10V, Negative-QTOFsplash10-00lr-3001900000-1d0d8bd1b59b2a55d8d82015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 20V, Negative-QTOFsplash10-02u0-2009600000-4ed9d1d982ffbd1508052015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 40V, Negative-QTOFsplash10-014i-9005000000-ba947fa438d494d461ee2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 10V, Negative-QTOFsplash10-00lr-3001900000-1d0d8bd1b59b2a55d8d82015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 20V, Negative-QTOFsplash10-02u0-2009600000-4ed9d1d982ffbd1508052015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 40V, Negative-QTOFsplash10-014i-9005000000-ba947fa438d494d461ee2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 10V, Positive-QTOFsplash10-001i-0000900000-315a366dbe558946edb02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 20V, Positive-QTOFsplash10-00lv-0473900000-1c4bdd89e12ee67d24cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 40V, Positive-QTOFsplash10-0aos-3943000000-2641710c36ccb16d4fcd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 10V, Negative-QTOFsplash10-001i-0000900000-f99193fc2ae16b7de32c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 20V, Negative-QTOFsplash10-001i-0000900000-ac627da97db59b607ca42021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Rockogenin 40V, Negative-QTOFsplash10-02u3-0801900000-01f0701dfa0d5e1c57f82021-09-25Wishart LabView Spectrum
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 IDFDB008457
KNApSAcK IDNot Available
Chemspider ID56619
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHalofuginone
METLIN IDNot Available
PubChem Compound62894
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.