Suberoylanilide hydroxamic acid (CED0002092)

Record Information
Version1.0
Creation Date2016-05-22 04:30:40 UTC
Update Date2026-08-19 06:56:14 UTC
Accession NumberCHEM017645
Identification
Common NameSuberoylanilide hydroxamic acid
ClassSmall Molecule
Description
Suberoylanilide hydroxamic acid belongs to the benzene and substituted derivatives, a class of benzenoids within the organic compounds. It has the chemical formula $\text{C}_{14}\text{H}_{20}\text{N}_2\text{O}_3$ and an average molecular weight of 264.32 g/mol. Biologically, this compound acts as an inhibitor (PMC3145497), a drug (PMC3145497), and a chelator (PMC7052901). It targets nine proteins, serving as an inhibitor of Histone deacetylase 1 (HDAC1), Histone deacetylase 2 (HDAC2), Histone deacetylase 3 (HDAC3), and Protein deacetylase HDAC6, along with five other proteins. The compound is recorded in 17 sources, including food preservation, antineoplastic agents in healthcare, pharmaceuticals and veterinary products, and household cleaning and consumer products such as perfumes within detergents and soaps, as well as non-electric simulated smoking devices. It is also found in electrical and electronic equipment, including amplifiers, antennas, electric hearing aids, auxiliary devices, and conductors or conductive bodies characterised by the conductive materials. The recorded exposure route is oral. Regarding health effects, subraylanilide hydroxamic acid is associated with cancer (PMC7824531), as well as an increase in neutropenia (PMC7581128) and thrombocytopenia (PMC7581128). Conversely, it is used as a treatment for cancer (PMC3145497) and has a therapeutic effect on glioblastoma (PMC12466395).
Contaminant TypeNot Available
Chemical Structure
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
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Organoleptic EffectsNot 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-006x-4920000000-0b60d0a81534425ab7beNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0859000000-0a83404097a3e01eb158Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001l-9750000000-d26ffebbce9b1bc73b92Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-7190000000-877b56b4601e9fa6d5b1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9220000000-99ea61440739c3064b34Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9100000000-6506e221f51e0d54cbd7Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-2190000000-9403e0edb1371ac82130Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-06ry-9360000000-2ac5220873ae653bb80dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9100000000-81d3844e3cacdfb678faNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0159-0490000000-8855a77bf8f5c1e58821Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6y-9740000000-3649f9eb7bb51fe7dcaaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9100000000-bbb1690ce5a4b45dd169Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0090000000-7aa1ceac7690e76ffdbeNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01ox-6190000000-ac3a50ce21bd2b6f7ef2Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9000000000-32187e1065af5e96be36Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2346.0Log mg/kg[1300:4200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
cancerassociated_withNot AvailablePMC7824531
canceris_treatment_forNot AvailablePMC3145497 , PMC3145497
neutropeniaassociated_withincreasePMC7581128
thrombocytopeniaassociated_withincreasePMC7581128
glioblastomahas_therapeutic_effect_onNot AvailablePMC12466395
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
358Antineoplastic agentsHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
530Radio Transmission SystemsElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
584BuoysMarine, shipping & aquacultureNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
630ToysRecreation & sports surfacesNot Available
632ApparelTextiles, leather & furnishingsNot Available
650Purses Luggage Hand BagsTextiles, leather & furnishingsNot Available
Pathways
1 pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Histone deacetylase 3 structureClick to view 3D structureHistone deacetylase 3O15379HumansPredicted (SEA)0.155698
Protein deacetylase HDAC6 structureClick to view 3D structureProtein deacetylase HDAC6Q9UBN7HumansPredicted (SEA)1.08989
Histone deacetylase 8 structureClick to view 3D structureHistone deacetylase 8Q9BY41HumansPredicted (SEA)0.544945
Histone deacetylase 5 structureClick to view 3D structureHistone deacetylase 5Q9UQL6HumansPredicted (SEA)0.389246
Histone deacetylase 2 structureClick to view 3D structureHistone deacetylase 2Q92769HumansPredicted (SEA)0.389246
Click to view 3D structurePolyamine deacetylase HDAC10Q969S8HumansPredicted (SEA)0.311397
Histone deacetylase 4 structureClick to view 3D structureHistone deacetylase 4P56524HumansPredicted (SEA)0.311397
Click to view 3D structureHistone deacetylase HD2Q94F81Zea maysPredicted (SEA)0.233548
Histone deacetylase 9 structureClick to view 3D structureHistone deacetylase 9Q9UKV0HumansPredicted (SEA)0.389246
Histone deacetylase 7 structureClick to view 3D structureHistone deacetylase 7Q8WUI4HumansPredicted (SEA)0.233548
Click to view 3D structureHistone deacetylaseQ7K6A1Plasmodium falciparum 3D7Predicted (SEA)0.155698
Click to view 3D structureHistone deacetylase 8A5H660Schistosoma mansoniPredicted (SEA)0.155698
Click to view 3D structureHistone deacetylase 11Q96DB2HumansPredicted (SEA)1.01204
Vascular endothelial growth factor receptor 2 structureClick to view 3D structureVascular endothelial growth factor receptor 2P35968HumansPredicted (SEA)71.6991
Leukotriene A-4 hydrolase structureClick to view 3D structureLeukotriene A-4 hydrolaseP09960HumansPredicted (SEA)0.155698
Epidermal growth factor receptor structureClick to view 3D structureEpidermal growth factor receptorP00533HumansPredicted (SEA)99.8806
Click to view 3D structureHistone deacetylase 6Q99P97Rattus norvegicusPredicted (SEA)0.856341
Heat shock protein HSP 90-alpha structureClick to view 3D structureHeat shock protein HSP 90-alphaP07900HumansPredicted (SEA)11.5217
Tyrosine-protein kinase JAK2 structureClick to view 3D structureTyrosine-protein kinase JAK2O60674HumansPredicted (SEA)78.1606
Bromodomain-containing protein 4 structureClick to view 3D structureBromodomain-containing protein 4O60885HumansPredicted (SEA)16.4262
Histone deacetylase-like amidohydrolase structureClick to view 3D structureHistone deacetylase-like amidohydrolaseQ70I53Alcaligenes sp. (strain DSM 11172)Predicted (SEA)0.155698
Receptor-type tyrosine-protein kinase FLT3 structureClick to view 3D structureReceptor-type tyrosine-protein kinase FLT3P36888HumansPredicted (SEA)141.296
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)100.97
Click to view 3D structureHistone deacetylase 1Q4QQW4Rattus norvegicusPredicted (SEA)0.700643
Histone deacetylase 1 structureClick to view 3D structureHistone deacetylase 1Q13547HumansPredicted (SEA)0.622794
Concentrations
Not Available
External Links
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.