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CHEBI ONTOLOGY - ANNOTATIONS

The Chemical Entities of Biological Interest (ChEBI) ontology is downloaded weekly from EMBL-EBI at http://www.ebi.ac.uk/chebi/. The data is made available under the Creative Commons License (CC BY 3.0, http://creativecommons.org/licenses/by/3.0/). For more information see: Degtyarenko et al. (2008) ChEBI: a database and ontology for chemical entities of biological interest. Nucleic Acids Res. 36, D344–D350.
Term:N,N-dimethylformamide
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Accession:CHEBI:17741 term browser browse the term
Definition:A member of the class of formamides that is formamide in which the amino hydrogens are replaced by methyl groups.
Synonyms:related_synonym: DMF;   Dimethylformamide;   Formula=C3H7NO;   InChI=1S/C3H7NO/c1-4(2)3-5/h3H,1-2H3;   InChIKey=ZMXDDKWLCZADIW-UHFFFAOYSA-N;   N,N-Dimethylmethanamide;   N-Formyldimethylamine;   SMILES=[H]C(=O)N(C)C
 alt_id: CHEBI:12425;   CHEBI:21454;   CHEBI:42077;   CHEBI:7076
 xref: CAS:68-12-2;   DrugBank:DB01844;   HMDB:HMDB0001888;   KEGG:C03134
 xref_mesh: MESH:D004126
 xref: MetaCyc:CPD-581;   PDBeChem:DMF;   PMID:18666198;   PMID:19608215;   PMID:23313473;   PMID:3824392;   Reaxys:605365;   Wikipedia:Dimethylformamide


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N,N-dimethylformamide term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb1b ATP-binding cassette, subfamily B (MDR/TAP), member 1B decreases expression EXP Dimethylformamide results in decreased expression of ABCB1B mRNA CTD PMID:12883083 NCBI chr 4:25,242,761...25,325,194
Ensembl chr 4:25,242,798...25,325,199 		JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions
increases expression		 ISO Thiocarbamates analog inhibits the reaction [Dimethylformamide results in increased expression of BAX protein] CTD PMID:29984871 NCBI chr 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368 		JBrowse link
G Bcl2l1 Bcl2-like 1 multiple interactions
increases expression		 EXP
ISO		 [Dimethylformamide co-treated with Carbon Tetrachloride] results in decreased expression of BCL2L1 protein
Dimethylformamide results in increased expression of BCL2L1 protein
Thiocarbamates analog inhibits the reaction [Dimethylformamide results in decreased expression of BCL2L1 protein]		 CTD PMID:20097184 PMID:29984871 NCBI chr 3:141,253,508...141,304,582
Ensembl chr 3:141,253,523...141,303,479 		JBrowse link
G Casp3 caspase 3 multiple interactions
increases expression		 EXP
ISO		 [Dimethylformamide co-treated with Carbon Tetrachloride] results in increased activity of CASP3 protein
Dimethylformamide results in increased expression of CASP3 protein modified form
CAT protein inhibits the reaction [Dimethylformamide results in increased expression of CASP3 protein modified form]; Thiocarbamates analog inhibits the reaction [Dimethylformamide results in increased expression of CASP3 protein modified form]		 CTD PMID:20097184 PMID:29984871 NCBI chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Casp9 caspase 9 multiple interactions
increases expression		 ISO CAT protein inhibits the reaction [Dimethylformamide results in increased expression of CASP9 protein modified form]; Thiocarbamates analog inhibits the reaction [Dimethylformamide results in increased expression of CASP9 protein modified form] CTD PMID:29984871 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626 		JBrowse link
G Cat catalase multiple interactions ISO CAT protein inhibits the reaction [Dimethylformamide results in increased expression of CASP3 protein modified form]; CAT protein inhibits the reaction [Dimethylformamide results in increased expression of CASP9 protein modified form]; CAT protein inhibits the reaction [Dimethylformamide results in increased expression of TP53 protein] CTD PMID:29984871 NCBI chr 3:89,842,393...89,874,577
Ensembl chr 3:89,842,399...89,874,478 		JBrowse link
G Cyp2e1 cytochrome P450, family 2, subfamily e, polypeptide 1 affects metabolic processing
increases response to substance
increases abundance
multiple interactions
increases expression
increases oxidation
increases metabolic processing		 ISO
EXP		 CYP2E1 protein polymorphism affects the metabolism of Dimethylformamide
CYP2E1 protein results in increased susceptibility to Dimethylformamide
CYP2E1 polymorphism results in increased abundance of Dimethylformamide metabolite
CYP2E1 protein affects the reaction [Dimethylformamide results in increased activity of GPT protein]; CYP2E1 protein affects the reaction [Dimethylformamide results in increased expression of HSP90B1 protein]
Dimethylformamide results in increased expression of CYP2E1 protein
CYP2E1 protein results in increased oxidation of Dimethylformamide
CYP2E1 protein affects the metabolism of Dimethylformamide
CYP2E1 protein results in increased metabolism of Dimethylformamide		 CTD PMID:9817075 PMID:10207612 PMID:11305777 PMID:15772367 PMID:29984871 More... NCBI chr 1:195,840,330...195,850,728
Ensembl chr 1:195,840,058...195,864,023 		JBrowse link
G Ddit3 DNA-damage inducible transcript 3 multiple interactions EXP [Dimethylformamide co-treated with Carbon Tetrachloride] results in increased expression of DDIT3 mRNA CTD PMID:20097184 NCBI chr 7:63,115,645...63,121,203
Ensembl chr 7:63,116,380...63,121,201 		JBrowse link
G Eif2ak3 eukaryotic translation initiation factor 2 alpha kinase 3 multiple interactions EXP [Dimethylformamide co-treated with Carbon Tetrachloride] results in increased expression of EIF2AK3 protein modified form CTD PMID:20097184 NCBI chr 4:102,805,495...102,866,914
Ensembl chr 4:102,805,510...102,866,911 		JBrowse link
G Gpt glutamic--pyruvic transaminase multiple interactions
increases activity		 ISO CYP2E1 protein affects the reaction [Dimethylformamide results in increased activity of GPT protein] CTD PMID:31501917 NCBI chr 7:108,416,646...108,419,495
Ensembl chr 7:108,416,642...108,419,494 		JBrowse link
G Gsr glutathione-disulfide reductase decreases expression EXP Dimethylformamide results in decreased expression of GSR mRNA CTD PMID:12883083 NCBI chr16:58,482,209...58,525,256
Ensembl chr16:58,482,505...58,525,661 		JBrowse link
G H2ax H2A.X variant histone increases expression ISO Dimethylformamide results in increased expression of H2AX protein CTD PMID:26387567 NCBI chr 8:44,671,927...44,673,257
Ensembl chr 8:44,671,786...44,673,239 		JBrowse link
G Hmox1 heme oxygenase 1 multiple interactions
decreases expression		 ISO Alitretinoin inhibits the reaction [Dimethylformamide results in decreased expression of HMOX1 protein]; U 0126 inhibits the reaction [Dimethylformamide results in decreased expression of HMOX1 protein]
Dimethylformamide results in decreased expression of HMOX1 mRNA; Dimethylformamide results in decreased expression of HMOX1 protein		 CTD PMID:31875996 NCBI chr19:13,466,287...13,474,082
Ensembl chr19:13,467,244...13,474,079 		JBrowse link
G Hsp90b1 heat shock protein 90 beta family member 1 multiple interactions
increases expression		 EXP
ISO		 [Dimethylformamide co-treated with Carbon Tetrachloride] results in increased expression of HSP90B1 protein
Dimethylformamide results in increased expression of HSP90B1 protein
CYP2E1 protein affects the reaction [Dimethylformamide results in increased expression of HSP90B1 protein]		 CTD PMID:20097184 PMID:31501917 NCBI chr 7:21,110,431...21,124,762
Ensembl chr 7:21,110,457...21,124,788 		JBrowse link
G Hspa5 heat shock protein family A (Hsp70) member 5 multiple interactions EXP [Dimethylformamide co-treated with Carbon Tetrachloride] results in increased expression of HSPA5 mRNA; [Dimethylformamide co-treated with Carbon Tetrachloride] results in increased expression of HSPA5 protein CTD PMID:20097184 NCBI chr 3:18,055,507...18,059,969
Ensembl chr 3:18,055,405...18,059,891 		JBrowse link
G Ltf lactotransferrin increases expression ISO Dimethylformamide results in increased expression of LTF mRNA CTD PMID:18063697 NCBI chr 8:110,999,948...111,022,795
Ensembl chr 8:110,999,948...111,022,795 		JBrowse link
G Mapk1 mitogen activated protein kinase 1 multiple interactions
increases phosphorylation		 ISO U 0126 inhibits the reaction [Dimethylformamide results in increased phosphorylation of MAPK1 protein]
[Dimethylformamide results in increased phosphorylation of MAPK1 protein] which results in increased phosphorylation of RXRA protein; Dimethylformamide results in increased phosphorylation of MAPK1 protein		 CTD PMID:31875996 NCBI chr11:83,957,813...84,023,629
Ensembl chr11:83,957,813...84,023,616 		JBrowse link
G Mapk3 mitogen activated protein kinase 3 increases phosphorylation
multiple interactions		 ISO [Dimethylformamide results in increased phosphorylation of MAPK3 protein] which results in increased phosphorylation of RXRA protein; Dimethylformamide results in increased phosphorylation of MAPK3 protein
U 0126 inhibits the reaction [Dimethylformamide results in increased phosphorylation of MAPK3 protein]		 CTD PMID:31875996 NCBI chr 1:181,366,646...181,372,863
Ensembl chr 1:181,366,637...181,372,863 		JBrowse link
G Mpo myeloperoxidase increases expression ISO Dimethylformamide results in increased expression of MPO mRNA CTD PMID:18063697 NCBI chr10:72,594,458...72,608,862
Ensembl chr10:72,594,661...72,604,819 		JBrowse link
G Mre11 MRE11 homolog, double strand break repair nuclease increases expression ISO Dimethylformamide results in increased expression of MRE11 mRNA; Dimethylformamide results in increased expression of MRE11 protein CTD PMID:26387567 NCBI chr 8:11,618,876...11,680,451
Ensembl chr 8:11,632,354...11,678,279 		JBrowse link
G Ncf1 neutrophil cytosolic factor 1 increases expression ISO Dimethylformamide results in increased expression of NCF1 mRNA CTD PMID:18063697 NCBI chr12:22,485,382...22,494,647
Ensembl chr12:22,485,451...22,494,646 		JBrowse link
G Nefh neurofilament heavy chain affects expression EXP Dimethylformamide affects the expression of NEFH mRNA CTD PMID:22954530 NCBI chr14:79,830,362...79,840,347
Ensembl chr14:79,830,362...79,840,351 		JBrowse link
G Nfe2l2 NFE2 like bZIP transcription factor 2 multiple interactions
decreases activity		 ISO Alitretinoin inhibits the reaction [Dimethylformamide results in decreased activity of NFE2L2 protein]; Dimethylformamide promotes the reaction [NFE2L2 protein binds to RXRA protein]; U 0126 inhibits the reaction [Dimethylformamide results in decreased activity of NFE2L2 protein] CTD PMID:31875996 NCBI chr 3:60,594,239...60,621,785
Ensembl chr 3:60,594,242...60,621,737 		JBrowse link
G Nqo1 NAD(P)H quinone dehydrogenase 1 multiple interactions
decreases expression		 ISO Alitretinoin inhibits the reaction [Dimethylformamide results in decreased expression of NQO1 protein]; U 0126 inhibits the reaction [Dimethylformamide results in decreased expression of NQO1 protein]
Dimethylformamide results in decreased expression of NQO1 mRNA; Dimethylformamide results in decreased expression of NQO1 protein		 CTD PMID:31875996 NCBI chr19:35,295,633...35,310,528
Ensembl chr19:35,295,573...35,310,557 		JBrowse link
G Parp1 poly (ADP-ribose) polymerase 1 multiple interactions EXP [Dimethylformamide co-treated with Carbon Tetrachloride] results in increased cleavage of PARP1 protein CTD PMID:20097184 NCBI chr13:92,307,593...92,339,406
Ensembl chr13:92,307,586...92,339,404 		JBrowse link
G Rad50 RAD50 double strand break repair protein increases expression ISO Dimethylformamide results in increased expression of RAD50 mRNA; Dimethylformamide results in increased expression of RAD50 protein CTD PMID:26387567 NCBI chr10:37,809,353...37,861,309
Ensembl chr10:37,808,726...37,861,396 		JBrowse link
G Rad51 RAD51 recombinase increases expression ISO Dimethylformamide results in increased expression of RAD51 mRNA; Dimethylformamide results in increased expression of RAD51 protein CTD PMID:26387567 NCBI chr 3:106,099,753...106,125,038
Ensembl chr 3:106,100,381...106,125,035 		JBrowse link
G Rxra retinoid X receptor alpha decreases degradation
multiple interactions
increases phosphorylation		 ISO Dimethylformamide results in decreased degradation of RXRA protein
Alitretinoin inhibits the reaction [Dimethylformamide results in decreased degradation of RXRA protein]; Dimethylformamide promotes the reaction [NFE2L2 protein binds to RXRA protein]; U 0126 inhibits the reaction [Dimethylformamide results in decreased degradation of RXRA protein]
[Dimethylformamide results in increased phosphorylation of MAPK1 protein] which results in increased phosphorylation of RXRA protein; [Dimethylformamide results in increased phosphorylation of MAPK3 protein] which results in increased phosphorylation of RXRA protein		 CTD PMID:31875996 NCBI chr 3:10,989,832...11,076,366
Ensembl chr 3:10,989,832...11,073,712 		JBrowse link
G Sod1 superoxide dismutase 1 increases expression ISO Dimethylformamide results in increased expression of SOD1 mRNA CTD PMID:35238128 NCBI chr11:29,456,673...29,462,249
Ensembl chr11:29,456,558...29,462,249 		JBrowse link
G Sult1a1 sulfotransferase family 1A member 1 multiple interactions ISO Dimethylformamide inhibits the reaction [SULT1A1 protein results in increased sulfation of 1-hydroxypyrene]; Dimethylformamide inhibits the reaction [SULT1A1 protein results in increased sulfation of 4-nitrophenol] CTD PMID:14570759 NCBI chr 1:181,272,022...181,276,750
Ensembl chr 1:181,272,023...181,275,562 		JBrowse link
G Sult2a1 sulfotransferase family 2A member 1 multiple interactions ISO Dimethylformamide inhibits the reaction [SULT2A1 protein results in increased sulfation of 1-hydroxypyrene] CTD PMID:14570759 NCBI chr 1:75,451,178...75,508,142
Ensembl chr 1:74,911,100...75,508,134 		JBrowse link
G Tnfsf10 TNF superfamily member 10 increases expression ISO Dimethylformamide results in increased expression of TNFSF10 mRNA; Dimethylformamide results in increased expression of TNFSF10 protein CTD PMID:18063697 NCBI chr 2:110,199,835...110,227,239
Ensembl chr 2:110,207,916...110,225,135 		JBrowse link
G Tp53 tumor protein p53 multiple interactions
increases expression		 ISO CAT protein inhibits the reaction [Dimethylformamide results in increased expression of TP53 protein]; Thiocarbamates analog inhibits the reaction [Dimethylformamide results in increased expression of TP53 protein]
Dimethylformamide results in increased expression of TP53 protein modified form		 CTD PMID:29984871 NCBI chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524 		JBrowse link
G Trim28 tripartite motif-containing 28 decreases expression ISO Dimethylformamide results in decreased expression of TRIM28 mRNA CTD PMID:35238128 NCBI chr 1:73,652,441...73,659,388
Ensembl chr 1:73,652,709...73,659,380 		JBrowse link
G Xrcc2 X-ray repair cross complementing 2 increases expression
affects expression		 ISO Dimethylformamide results in increased expression of XRCC2 protein
Dimethylformamide affects the expression of XRCC2 mRNA		 CTD PMID:26387567 NCBI chr 4:9,423,873...9,502,980
Ensembl chr 4:9,423,898...9,442,482 		JBrowse link
G Xrcc3 X-ray repair cross complementing 3 increases expression ISO Dimethylformamide results in increased expression of XRCC3 mRNA; Dimethylformamide results in increased expression of XRCC3 protein CTD PMID:26387567 NCBI chr 6:130,863,405...130,873,765
Ensembl chr 6:130,863,959...130,872,444 		JBrowse link
G Zp2 zona pellucida glycoprotein 2 increases expression ISO Dimethylformamide results in increased expression of ZP2 mRNA CTD PMID:35238128 NCBI chr 1:174,513,507...174,525,288
Ensembl chr 1:174,513,511...174,525,288 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19818
    role 19790
      application 19622
        solvent 16738
          formamide 134
            N,N-dimethylformamide 37
              N,N-dimethylformamide dimethyl acetal 0
Path 2
Term Annotations click to browse term
  CHEBI ontology 19818
    subatomic particle 19816
      composite particle 19816
        hadron 19816
          baryon 19816
            nucleon 19816
              atomic nucleus 19816
                atom 19816
                  main group element atom 19761
                    p-block element atom 19761
                      carbon group element atom 19703
                        carbon atom 19698
                          organic molecular entity 19698
                            organic group 18905
                              organic divalent group 18887
                                organodiyl group 18887
                                  carbonyl group 18853
                                    carbonyl compound 18853
                                      carboxylic acid 18569
                                        carboacyl group 17687
                                          univalent carboacyl group 17687
                                            carbamoyl group 17531
                                              carboxamide 17531
                                                formamides 1807
                                                  formamide 134
                                                    N,N-dimethylformamide 37
                                                      N,N-dimethylformamide dimethyl acetal 0
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