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Showing metabocard for Vorinostat (HMDB0015568)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:51 UTC
HMDB IDHMDB0015568
Secondary Accession Numbers
  • HMDB15568
Metabolite Identification
Common NameVorinostat
DescriptionVorinostat, also known as SAHA or zolinza, 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. Vorinostat is a drug which is used for the treatment of cutaneous manifestations in patients with cutaneous t-cell lymphoma who have progressive, persistent or recurrent disease on or following two systemic therapies. A recent study suggested that vorinostat also possesses some activity against recurrent glioblastoma multiforme, resulting in a median overall survival of 5.7 months (compared to 4 - 4.4 months in earlier studies). Vorinostat is an extremely weak basic (essentially neutral) compound (based on its pKa). In some cancer cells, there is an overexpression of HDACs, or an aberrant recruitment of HDACs to oncogenic transcription factors causing hypoacetylation of core nucleosomal histones. Vorinostat (rINN) or Vorinostat (SAHA), is a drug currently under investigation for the treatment of cutaneous T cell lymphoma (CTCL), a type of skin cancer, to be used when the disease persists, gets worse, or comes back during or after treatment with other medicines. Further brain tumor trials are planned using combinations of vorinostat with other drugs. The mechanism of the antineoplastic effect of vorinostat has not been fully characterized. I) and HDAC6 (Class. It is the first in a new class of agents known as histone deacetylase inhibitors. Both metabolites are pharmacologically inactive.
Structure
Data?1582753311
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 acidMeSH
18F Suberoylanilide hydroxamic acidMeSH
N Hydroxy n' phenyloctanediamideMeSH
N1 Hydroxy N8 phenyloctanediamideMeSH
Chemical FormulaC14H20N2O3
Average Molecular Weight264.3202
Monoisotopic Molecular Weight264.147392516
IUPAC NameN-hydroxy-N'-phenyloctanediamide
Traditional NameSAHA
CAS Registry Number149647-78-9
SMILES
ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1
InChI Identifier
InChI=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
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.072 g/LNot Available
LogPNot AvailableNot 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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-4920000000-0b60d0a81534425ab7beSpectrum
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
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB02546 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB02546 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02546
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5120
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVorinostat
METLIN IDNot Available
PubChem Compound5311
PDB IDSHH
ChEBI ID45716
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:16928817 ]

Enzymes

Enzyme Details
1. Histone deacetylase 2
General function:
Involved in histone deacetylase activity
Specific function:
Forms transcriptional repressor complexes by associating with MAD, SIN3, YY1 and N-COR. Interacts in the late S-phase of DNA-replication with DNMT1 in the other transcriptional repressor complex composed of DNMT1, DMAP1, PCNA, CAF1. Deacetylates TSHZ3 and regulates its transcriptional repressor activity
Gene Name:
HDAC2
Uniprot ID:
Q92769
Molecular weight:
55363.9
References
  1. Xu WS, Parmigiani RB, Marks PA: Histone deacetylase inhibitors: molecular mechanisms of action. Oncogene. 2007 Aug 13;26(37):5541-52. [PubMed:17694093 ]
Enzyme Details
2. Histone deacetylase 3
General function:
Involved in histone deacetylase activity
Specific function:
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an important role in transcriptional regulation, cell cycle progression and developmental events. Histone deacetylases act via the formation of large multiprotein complexes. Probably participates in the regulation of transcription through its binding to the zinc-finger transcription factor YY1; increases YY1 repression activity. Required to repress transcription of the POU1F1 transcription factor
Gene Name:
HDAC3
Uniprot ID:
O15379
Molecular weight:
48847.4
References
  1. Xu WS, Parmigiani RB, Marks PA: Histone deacetylase inhibitors: molecular mechanisms of action. Oncogene. 2007 Aug 13;26(37):5541-52. [PubMed:17694093 ]