HEDD

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The Human Epigenetic Drug Database (HEDD) is a comprehensive web-based database for epigenetic drugs, which focuses on the storage and integration of epigenetic drug datasets that were obtained from laboratory experiments that is essential for understanding the mechanism of action of these epigenetic drugs at a systematic level.

Valproic acid

Category:	HDACi
Cas Number:	99-66-1
Molecular Formula:	C₈H₁₆O₂
Molecular Weight:	166.193269 g/mol
Smiles:	CCCC(CCC)C(=O)O
Description:	Valproic Acid is a synthetic derivative of propylpentanoic acid with antiepileptic properties and potential antineoplastic and antiangiogenesis activities. In epilepsy, valproic acid appears to act by increasing the concentration of gamma-aminobutyric acid (GABA) in the brain. This agent's antitumor and antiangiogenesis activities may be related to the inhibition of histone deacetylases and nitric oxide synthase, which results in the inhibition of nitric oxide synthesis. (NCI04)
synonyms:	VALPROIC ACID 2-Propylpentanoic acid Depakine Depakene 99-66-1 Dipropylacetic acid Valproate Ergenyl Mylproin 2-Propylvaleric acid Convulex Di-n-propylacetic acid n-Dipropylacetic acid Propylvaleric acid Myproic Acid Pentanoic acid, 2-propyl- Di-n-propylessigsaure n-DPA Dipropylacetate Avugane Depakin Baceca 4-Heptanecarboxylic acid Novo-Valproic Nu-Valproic divalproex PMS-Valproic Acid Deproic Savicol Vupral Depakin chrono Depakine chrono Kyselina 2-propylvalerova Alti-Valproic Penta-Valproic Dom-Valproic Med Valproic 2-n-Propyl-n-valeric acid Acetic acid, dipropyl- Valproic acid USP Valcote Valparin Epilim Epival Valeric acid, 2-propyl- Convulsofin Valproinsaeure Stavzor Acido valproico Sandoz valproic Valproate sodium Apo-valproic Acide valproique Epival er APO-divalproex DOM-divalproex Acidum valproicum Abbott 44090 Dom-valproic acid Acide valproique [INN-French] Acido valproico [INN-Spanish] Acidum valproicum [INN-Latin] Di-n-propylessigsaure [German] Apo-valproic syrup PHL-valproic acid Delepsine Epiject I.V. Sprinkle Epilex Kyselina 2-propylvalerova [Czech] PEAC Di-n-propylessigsaeure Valproic acid (USP) Valproic acid USP24 Myproate Dom-valproic acid syrup 2-propylpentanoate 2 PP (base) Dom-valproate Gen-divalproex Novo-divalproex PHL-valproate PMS-valproate DOM-valproic acid E.C. PHL-valproic acid E.C. PMS-Divalproex PMS-valproic acid E.C. CHEMBL109 DPA (VAN) (n-C3H7)2CHCOOH UNII-614OI1Z5WI Divalproex-125 Divalproex-250 Divalproex-500 NSC 93819 Depakene (TN) Depakote (TM) 2-propyl-Pentanoate Valproic-250 2-PROPYL-PENTANOIC ACID Depakene Cap 500mg CHEBI:39867 nchembio815-comp21 HSDB 3582 Novo-Valproic - ECC Nu-Divalproex 125mg Nu-Divalproex 250mg Nu-Divalproex 500mg Spectrum_000521 Ratio-Valproic - ECC AC1Q2ULA S(-)-4-En-valproate Spectrum2_000946 Spectrum3_001733 Spectrum4_000376 EINECS 202-777-3 Valproic Acid, Sodium Salt (2:1) SBB065764 VPA Novo-valproic soft gel cap Valproate semisodique [French] Valproato semisodico [Spanish] PMS-Divalproex (125mg) PMS-Divalproex (500mg) Ratio-Valproic-Cap 250mg Valproatum seminatricum [Latin] AC1L1F7T BRN 1750447 S(-)-4-En-valproic acid S-2-n-Propyl-4-pentenoate NCGC00091149-01 (S)-2-propyl-4-pentanoate KBioGR_000871 KBioGR_002277 KBioSS_001001 KBioSS_002278 BIDD:GT0858 DivK1c_000273 P6273_SIGMA SPBio_000912 AI3-10500 MLS001076682 MLS001335927 MLS001335928 MLS002415770 Ratio-Valproic 50mg/mL Syrup Sodium hydrogen divalproic acid S-2-n-Propyl-4-pentenoic acid WLN: QVY3 & 3 KBio1_000273 KBio2_001001 KBio2_002277 KBio2_003569 KBio2_004845 KBio2_006137 KBio2_007413 KBio3_002626 KBio3_002757 NIJJYAXOARWZEE-UHFFFAOYSA- (S)-2-Propyl-4-pentanoic acid Valproic acid [USAN:BAN:INN] Valproic acid [USAN:INN:BAN] CID3121 NINDS_000273 NIJJYAXOARWZEE-UHFFFAOYSA-N HMS2089J06 NSC93819 nchembio.79-comp4 DB00313 G2M-777 LS-2068 NCGC00091149-02 NCGC00091149-03 NCGC00091149-04 CPD000499581 SAM002564230 SMR000499581 LS-161170 P0823 DSSTox_CID_3733 DEPACON 76584-70-8 (hydrochloride salt (2:1)) C07185 D00399 DSSTox_RID_77171 DSSTox_GSID_23733 I04-0211 MolPort-001-791-895 CAS-99-66-1 InChI=1/C8H16O2/c1-3-5-7(6-4-2)8(9)10/h7H,3-6H2,1-2H3,(H,9,10) Depakotereg Valproinsaure Deprakine Encorate Epilimreg Valproic Teva-divalproex Mylan-valproic Ratio-valproic A-44090 Deproic Syrup Mylan-divalproex PHL-divalproex Depakote Sprinkles Ftp-valproic Acid Nu-valproic Syrup Epical (TM) Epilim (Salt/Mix) Divalproex Sodium Dr Epival Ect 125mg Epival Ect 250mg Epival Ect 500mg Depacon (Salt/Mix) Divalproex Sodium ER Convulex (Salt/Mix) Depakene Cap 250mg Eurekene (Salt/Mix) Valparin (Salt/Mix) Penta-valproic Capsules Divalproex (Salt/Mix) Valdisoval (Salt/Mix) ACMC-209sdq 2 -propylpentanoic acid di-n-propyl acetic acid 2-n-propylpentanoic acid Tick anticoagulant peptide PMS-divalproex (250mg) SCHEMBL2275 2,2-di-n-propylacetic acid Gen-Valproic - Cap 250mg KSC493G8T Ratio-valproic - Ecc 500mg 614OI1Z5WI GTPL7009 CTK3J3389 HMDB01877 Divalproex Sodium Delayed Release Divalproex Sodium Delayed-release Divalproex Sodium Extended-release Divalproex Sodium Extended Release HMS2231E06 HMS3259C18 HMS3370C21 ACT05281 ZINC3008621 Tox21_111091 Tox21_201963 Tox21_300603 ANW-41052 BDBM50003616 DAP000831 DCL001031 DNC001445 LMFA01020291 MFCD00002672 NSC-93819 STL445581 Valproic acid [USAN:USP:INN:BAN] AKOS009156895 Tox21_111091_1 CCG-221127 CS-1765 CS-T-46266 MCULE-7136317196 NC00584 RL06134 RTR-031980 TRA0085608 NCGC00091149-05 NCGC00091149-06 NCGC00091149-08 NCGC00091149-09 NCGC00162288-07 NCGC00254365-01 NCGC00259512-01 2-propylpentanoic acid (ACD/Name 4.0) AJ-44336 AK128830 AN-24519 HY-10585 KB-69563 OR025555 OR133876 AB0009719 TR-031980 791-EP2306789A1 Divalproex Sodium Delayed Release (sprinkle) FT-0609289 6400-EP1441224A2 6400-EP2272537A2 6400-EP2272827A1 6400-EP2275420A1 6400-EP2280008A2 6400-EP2298764A1 6400-EP2298765A1 6400-EP2308867A2 6400-EP2308870A2 6400-EP2311494A1 6400-EP2311840A1 6400-EP2314585A1 6400-EP2374790A1 A19450 Divalproex Sodiumdelayed-release Delayed-release AB00698315-06 Q-200321 Sodium valproate; 2-Propylpentanoic acid sodium salt 3B3-036259
Structure:
3D Conformer:	3D View
Downlaod:	Structure File Download (4.0KB)

Target list

Id	Drug Name	Target	PubmedId	Co-crystal Complex
938	valproic acid	Acyl-CoA: cholesterol acyltransferase (ACAT) (Homo sapiens (Human))	23386702
939	valproic acid	UDP-glucuronosyltransferase 2B7 (Homo sapiens)	15781124
940	valproic acid	Carboxylesterase 2 (Homo sapiens)	23386702
941	valproic acid	Cytochrome P450 2A6 (Homo sapiens (Human))	16248836
942	valproic acid	Coagulation factor VII/tissue factor (Homo sapiens)	17675290
943	valproic acid	Histone deacetylase 1 (HDAC1) (Homo sapiens (human))	21874153
944	valproic acid	istone deacetylase (HDAC1 and HDAC2) (Homo sapiens (human))	21874153
945	valproic acid	Histone deacetylase 3 (Homo sapiens (human))	21874153
946	valproic acid	Histone deacetylase 8 (Homo sapiens (human))	21874153
947	valproic acid	Histone deacetylase 4 (HDAC4) (Homo sapiens (Human))	21874153
948	valproic acid	Histone deacetylase 5 (HDAC5) (Homo sapiens (Human))	21874153
949	valproic acid	Histone deacetylase (Homo sapiens (human))	21874153
950	valproic acid	Histone deacetylase 9 (HDAC9) (Homo sapiens (Human))	21874153
951	valproic acid	Histone deacetylase (Homo sapiens (human))	21874153
952	valproic acid	Aldose reductase (Rattus norvegicus)	23312612
953	valproic acid	Aldose reductase (Rattus norvegicus)	24630695
954	valproic acid	Aldose reductase-related protein 1 (Rattus norvegicus)	25695864
955	valproic acid	Aldose reductase (Bos taurus)	26005026
956	valproic acid	Coagulation factor VII/tissue factor (Homo sapiens)	17675290
957	valproic acid	Aldehyde reductase (Homo sapiens (human))	20936791

Disease list

Conditions	Drug Name	Status	Nct Number	Phases
Advanced cancers	5-Azacytidine valproic acid	Completed	NCT00496444	Phase 1
Brain metastases	Temozolomide valproic acid	Terminated	NCT00437957	Phase 1
HIV infections	Enfuvirtide valproic acid	Terminated	NCT00312546	Phase 1
Lymphoma	5-Aza-2'-deoxycytidine Valproic acid	Completed	NCT00109824	Phase 1
MDS AML	5-Azacytidine Valproic acid ATRA	Completed	NCT01575691	Phase 1
Advanced cancers	5-Azacytidine Valproic acid	Completed	NCT00496444	Phase 1
Malignant melanoma	Karenitecin valproic acid	Terminated	NCT00358319	Phase 1 2
ALPS\|hypersplenism\|lymphadenopathy	Valproic acid	Completed	NCT00605657	Phase 1 2
Leukemia MDS	5-Aza-2'-deoxycytidine Valproic acid	Completed	NCT00075010	Phase 1 2
Chronic lymphocytic leukemia	Valproic acid fludarabine	Terminated	NCT00524667	Phase 2
Myelodysplastic syndromes	5-Azacytidine valproic acid ATRA	Completed	NCT00439673	Phase 2
AML MDS	5-Azacytidine valproic acid retinoic acid	Completed	NCT00339196	Phase 2
HIV infections	Raltegravir valproic acid	Terminated	NCT00614458	Phase 2
AML\|MDS	5-Azacytidine Valproic acid ATRA	Completed	NCT00339196	Phase 2
MDSs	5-Azacytidine Valproic acid ATRA	Completed	NCT00439673	Phase 2
MDS AML	5-Azacytidine Valproic acid ATRA	Completed	NCT00326170	Phase 2
AML MDS leukemia	5-Azacytidine Ara-C Valproic acid	Completed	NCT00382590	Phase 2
HTLV-I-associated myelopathy	Valproic acid	Terminated	NCT00519181	PHN.A
lymphoma cell leu-kemia	Suberoylanilide hydroxamic acid Valproic acid			Preclinical study
epilepsy	Valproic acid			Preclinical study

High-throughoutput Dataset

Title	Drug Name	Category	Sample type	PMID
Transcriptional response to histone deacetylase inhibitors	Suberoylanilide hydroxamic acid Valproic acid	HDACi	human lymphoma cell leu-kemia cells (LCL cells)
Expression data from untreated and valproic acid (VPA) treated CD34+ Hematopoietic Stem Cells (HSCs)	Valproic acid	HDACi	human CD34+ cells	22885124
A Multi-loop, Double-cube Microarray Design Applied to Prostate Cancer Cell Lines with Variable Sensitivity to Histone Deacetylase Inhibitor	Suberoylanilide hydroxamic acid Valproic acid	HDACi	human Prostate Cancer Cell Lines (DU-145 and PC3)	18980983
Gene expression of VPA and GEM	Valproic acid	HDACi	human cholangiocarcinoma cell line (HuCCT1)
BCL6 repression of EP300 provides a basis for rational combinatorial therapy in diffuse large B cell lymphomas	Suberoylanilide hydroxamic acid Valproic acid Trichostatin A	HDACi	human diffuse large B-cell lymphomas cell lines (DLBCL cell lines)	21041953
Antileukemic activity of valproic acid in chronic lymphocytic leukemia cells defined by microarray analysis	Valproic acid	HDACi	chronic lymphocytic leukemia cells obtained from 14 patients	19710697
Valproic Acid Confers Functional Pluripotency to Human Amniotic Fluid Stem Cells in a Transgene-free Approach	Valproic acid	HDACi	human Amniotic Fluid Stem Cells human embryonic stem cells	22760542
Profile of gene expression in K562 cells exposed to 2 mM sodium valproate for 12 hours using Agilent SurePrint G3 Human GE 8x60K Microarray	Valproic acid	HDACi	human K562 cells	22701306
A transcriptome-based classifier to identify developmental toxicants by stem cell testing: design, validation, and optimization for histone deacetylase inhibitors	Valproic acid trichostatin A Suberoylanilide hydroxamic acid Belinostat Panobinostat Entinostat	HDACi	human embryonic stem cells (hESCs)	26272509
Gene expression profiles of Histone deacetylase inhibitors treated cord blood hematopoietic stem cells.	Valproic acid	HDACi	human cord blood CD34+ cells
CCAAT/enhancer-binding protein alpha is epigenetically silenced by histone acetylation in endometriosis and promotes the pathogenesis of endometriosis: a novel therapeutic target	5-Aza-2'-deoxycytidine Valproic acid	DNMTi HDACi	human endometriotic cyst stromal cells (ECSCs)	23833041
In vitro assessment of drug-induced liver steatosis based on human dermal stem cell-derived hepatic cells.	valproic acid	HDACi	Human skin-derived precursor cells (hSKP)	25716160
U937 treated with decitabine, panobinostat and valproic acid	5-Aza-2'-deoxycytidine panobinostat valproic acid	DNMTi HDACi	AML cell line model U937
OCI/AML2 ATRA AND VPA GENE EXPRESSION	valproic acid	HDACi	OCI/AML-2 cells	15902297
Theca cell gene expression	valproic acid	HDACi	Polycystic ovary syndrome (PCOS) theca cells	15598877
Human embryonic stem cell based neuro-developmental toxicity assay: response to valproic acid and carbamazepine exposure	valproic acid carbamazepine	HDACi	human embryonic stem cell (hESC)	25979313
Toxicology study on KhES-3 cells.	valproic acid	HDACi	human embryonic stem cell (hESC)
Gene expression in INA6 multiple myeloma cells in an acidic condition	valproic acid	HDACi	INA6 multiple myeloma cells
Expression data for developing a GE-HTS signature for neuroblastoma differentiation	valproic acid	HDACi	BE(2)-C cells
Gene expression profile of the human leukemia cell line Reh after treatment with bortezomib, valproic acid or a combination of both.	valproic acid	HDACi	human leukemia cell line Reh	23357978

Complex list

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Target

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About

The Human Epigenetic Drug Database (HEDD) is a comprehensive web-based database for epigenetic drugs, which focuses on integrating epigenetic drug studies based Omics data from high through experiments that is essential for understanding the mechanism of action of these epigenetic drugs at a systematic level.