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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:52:02 UTC
HMDB IDHMDB0015568
Secondary Accession Numbers
  • HMDB15568
Metabolite Identification
Common NameVorinostat
DescriptionVorinostat (rINN) or suberoylanilide hydroxamic acid (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. It is the first in a new class of agents known as histone deacetylase inhibitors. 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). Further brain tumor trials are planned in which vorinostat will be combined with other drugs. [Wikipedia ]
Structure
Data?1582753311
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 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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.072 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+164.09731661259
DarkChem[M-H]-164.24931661259
DeepCCS[M+H]+164.47530932474
DeepCCS[M-H]-162.11730932474
DeepCCS[M-2H]-195.21130932474
DeepCCS[M+Na]+170.56830932474
AllCCS[M+H]+160.732859911
AllCCS[M+H-H2O]+157.432859911
AllCCS[M+NH4]+163.732859911
AllCCS[M+Na]+164.532859911
AllCCS[M-H]-165.532859911
AllCCS[M+Na-2H]-165.932859911
AllCCS[M+HCOO]-166.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
VorinostatONC(=O)CCCCCCC(=O)NC1=CC=CC=C13464.6Standard polar33892256
VorinostatONC(=O)CCCCCCC(=O)NC1=CC=CC=C12514.8Standard non polar33892256
VorinostatONC(=O)CCCCCCC(=O)NC1=CC=CC=C12618.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Vorinostat,1TMS,isomer #1C[Si](C)(C)N(O)C(=O)CCCCCCC(=O)NC1=CC=CC=C12634.4Semi standard non polar33892256
Vorinostat,1TMS,isomer #1C[Si](C)(C)N(O)C(=O)CCCCCCC(=O)NC1=CC=CC=C12452.2Standard non polar33892256
Vorinostat,1TMS,isomer #1C[Si](C)(C)N(O)C(=O)CCCCCCC(=O)NC1=CC=CC=C13411.3Standard polar33892256
Vorinostat,1TMS,isomer #2C[Si](C)(C)N(C(=O)CCCCCCC(=O)NO)C1=CC=CC=C12467.5Semi standard non polar33892256
Vorinostat,1TMS,isomer #2C[Si](C)(C)N(C(=O)CCCCCCC(=O)NO)C1=CC=CC=C12397.1Standard non polar33892256
Vorinostat,1TMS,isomer #2C[Si](C)(C)N(C(=O)CCCCCCC(=O)NO)C1=CC=CC=C13215.8Standard polar33892256
Vorinostat,2TMS,isomer #1C[Si](C)(C)N(O)C(=O)CCCCCCC(=O)N(C1=CC=CC=C1)[Si](C)(C)C2399.6Semi standard non polar33892256
Vorinostat,2TMS,isomer #1C[Si](C)(C)N(O)C(=O)CCCCCCC(=O)N(C1=CC=CC=C1)[Si](C)(C)C2396.7Standard non polar33892256
Vorinostat,2TMS,isomer #1C[Si](C)(C)N(O)C(=O)CCCCCCC(=O)N(C1=CC=CC=C1)[Si](C)(C)C3073.7Standard polar33892256
Vorinostat,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(O)C(=O)CCCCCCC(=O)NC1=CC=CC=C12841.9Semi standard non polar33892256
Vorinostat,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(O)C(=O)CCCCCCC(=O)NC1=CC=CC=C12641.3Standard non polar33892256
Vorinostat,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(O)C(=O)CCCCCCC(=O)NC1=CC=CC=C13412.8Standard polar33892256
Vorinostat,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)CCCCCCC(=O)NO)C1=CC=CC=C12710.0Semi standard non polar33892256
Vorinostat,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)CCCCCCC(=O)NO)C1=CC=CC=C12615.2Standard non polar33892256
Vorinostat,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(C(=O)CCCCCCC(=O)NO)C1=CC=CC=C13247.8Standard polar33892256
Vorinostat,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(O)C(=O)CCCCCCC(=O)N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2886.2Semi standard non polar33892256
Vorinostat,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(O)C(=O)CCCCCCC(=O)N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C2767.8Standard non polar33892256
Vorinostat,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(O)C(=O)CCCCCCC(=O)N(C1=CC=CC=C1)[Si](C)(C)C(C)(C)C3193.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vorinostat GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-4920000000-0b60d0a81534425ab7be2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Vorinostat GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Vorinostat LC-ESI-Hybrid FT , Positive-QTOFsplash10-0udi-0859000000-0a83404097a3e01eb1582017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vorinostat , positive-QTOFsplash10-001l-9750000000-d26ffebbce9b1bc73b922017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vorinostat 10V, Positive-QTOFsplash10-00kf-7190000000-877b56b4601e9fa6d5b12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vorinostat 20V, Positive-QTOFsplash10-0006-9220000000-99ea61440739c3064b342016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vorinostat 40V, Positive-QTOFsplash10-0006-9100000000-6506e221f51e0d54cbd72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vorinostat 10V, Negative-QTOFsplash10-03di-2190000000-9403e0edb1371ac821302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vorinostat 20V, Negative-QTOFsplash10-06ry-9360000000-2ac5220873ae653bb80d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vorinostat 40V, Negative-QTOFsplash10-0006-9100000000-81d3844e3cacdfb678fa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vorinostat 10V, Positive-QTOFsplash10-0159-0490000000-8855a77bf8f5c1e588212021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vorinostat 20V, Positive-QTOFsplash10-0f6y-9740000000-3649f9eb7bb51fe7dcaa2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vorinostat 40V, Positive-QTOFsplash10-0006-9100000000-bbb1690ce5a4b45dd1692021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vorinostat 10V, Negative-QTOFsplash10-03di-0090000000-7aa1ceac7690e76ffdbe2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vorinostat 20V, Negative-QTOFsplash10-01ox-6190000000-ac3a50ce21bd2b6f7ef22021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vorinostat 40V, Negative-QTOFsplash10-0006-9000000000-32187e1065af5e96be362021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB02546 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
MarkerDB IDNot Available
Good Scents 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

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 ]
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 ]