Suberoylanilide hydroxamic acid (CHEM017645)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 04:30:40 UTC
Update Date2016-11-09 01:15:38 UTC
Accession NumberCHEM017645
Identification
Common NameSuberoylanilide hydroxamic acid
ClassSmall Molecule
DescriptionA dicarboxylic acid diamide comprising suberic (octanedioic) acid coupled to aniline and hydroxylamine. A histone deacetylase inhibitor, it is marketed under the name Zolinza for the treatment of cutaneous T cell lymphoma (CTCL).
Contaminant Sources
  • HMDB Contaminants - Urine
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Octanedioic acid hydroxyamide phenylamideChEBI
SAHAChEBI
SHHChEBI
Suberanilohydroxamic acidChEBI
Suberoylanilide hydroxamic acidChEBI
VorinostatumChEBI
ZolinzaChEBI
Octanedioate hydroxyamide phenylamideGenerator
SuberanilohydroxamateGenerator
Suberoylanilide hydroxamateGenerator
MK0683HMDB
N-Hydroxy-n'-phenyloctanediamideHMDB
N-Hyrdroxy-n'-phenyloctanediamideHMDB
18F-SAHAHMDB
18F-Suberoylanilide hydroxamic acidHMDB
Merck brand OF vorinostatHMDB
N1-Hydroxy-N8-phenyloctanediamideHMDB
NHNPODAHMDB
Suberoyl anilide hydroxamic acidHMDB
18F Suberoylanilide hydroxamic acidHMDB
N Hydroxy n' phenyloctanediamideHMDB
N1 Hydroxy N8 phenyloctanediamideHMDB
Chemical FormulaC14H20N2O3
Average Molecular Mass264.320 g/mol
Monoisotopic Mass264.147 g/mol
CAS Registry Number149647-78-9
IUPAC NameN-hydroxy-N'-phenyloctanediamide
Traditional NameSAHA
SMILESONC(=O)CCCCCCC(=O)NC1=CC=CC=C1
InChI IdentifierInChI=1S/C14H20N2O3/c17-13(15-12-8-4-3-5-9-12)10-6-1-2-7-11-14(18)16-19/h3-5,8-9,19H,1-2,6-7,10-11H2,(H,15,17)(H,16,18)
InChI KeyWAEXFXRVDQXREF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility0.072 g/LALOGPS
logP1.88ALOGPS
logP2ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)8.91ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area78.43 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity73.81 m³·mol⁻¹ChemAxon
Polarizability28.39 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-4920000000-0b60d0a81534425ab7beSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-Hybrid FT , Positivesplash10-0udi-0859000000-0a83404097a3e01eb158Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001l-9750000000-d26ffebbce9b1bc73b92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-7190000000-877b56b4601e9fa6d5b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9220000000-99ea61440739c3064b34Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-6506e221f51e0d54cbd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2190000000-9403e0edb1371ac82130Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06ry-9360000000-2ac5220873ae653bb80dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-81d3844e3cacdfb678faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0159-0490000000-8855a77bf8f5c1e58821Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6y-9740000000-3649f9eb7bb51fe7dcaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-bbb1690ce5a4b45dd169Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-7aa1ceac7690e76ffdbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ox-6190000000-ac3a50ce21bd2b6f7ef2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-32187e1065af5e96be36Spectrum
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 IDDB02546
HMDB IDHMDB0015568
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDSHH
Wikipedia LinkVorinostat
Chemspider ID5120
ChEBI ID45716
PubChem Compound ID5311
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=21657958
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=22887890
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23320102
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23348693
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23708756
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23758082
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23820962
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23864881
9. Munshi A, Tanaka T, Hobbs ML, Tucker SL, Richon VM, Meyn RE: Vorinostat, a histone deacetylase inhibitor, enhances the response of human tumor cells to ionizing radiation through prolongation of gamma-H2AX foci. Mol Cancer Ther. 2006 Aug;5(8):1967-74.