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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:4-hydroperoxycyclophosphamide
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Accession:CHEBI:196991 term browser browse the term
Definition:A phosphorodiamide that is the active metabolite of the nitrogen mustard cyclophosphamide. It has potent antineoplastic and immunosuppressive properties.
Synonyms:exact_synonym: 2-[bis(2-chloroethyl)amino]-2-oxido-1,3,2-oxazaphosphinan-4-yl hydroperoxide
 related_synonym: 2-(Bis(2-chloroethyl)amino)-4-hydroperoxytetrahydro-2H-1,3,2-oxazaphosphorine;   2-(bis(2-chloroethyl)amino)tetrahydro-2-oxideo-2H-1,3,2-oxazaphosphorin-4-yl hydroperoxide;   4-Hydroperoxycyclofosfamide;   4-OOH Cyclophosphamide;   Formula=C7H15Cl2N2O4P;   InChI=1S/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(13)10-7(15-12)1-6-14-16/h7,12H,1-6H2,(H,10,13);   InChIKey=VPAWVRUHMJVRHU-UHFFFAOYSA-N;   Perfosfamide (unspecified);   SMILES=OOC1CCOP(=O)(N1)N(CCCl)CCCl
 xref: CAS:39800-16-3
 xref_mesh: MESH:C011272
 xref: PMID:8024619;   Patent:NL7208895;   Patent:US3808297;   Reaxys:531579


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4-hydroperoxycyclophosphamide term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abl1 ABL proto-oncogene 1, non-receptor tyrosine kinase increases expression ISO perfosfamide results in increased expression of ABL1 mRNA CTD PMID:19429390 NCBI chr 3:35,377,587...35,480,843
Ensembl chr 3:35,377,391...35,480,846 		JBrowse link
G Actb actin, beta decreases expression ISO perfosfamide results in decreased expression of ACTB mRNA CTD PMID:19429390 NCBI chr12:16,776,664...16,779,634
Ensembl chr12:16,776,661...16,780,242 		JBrowse link
G Agt angiotensinogen decreases response to substance ISO AGT protein results in decreased susceptibility to perfosfamide CTD PMID:11034089 NCBI chr19:69,426,540...69,447,017
Ensembl chr19:69,421,638...69,446,944 		JBrowse link
G Aifm1 apoptosis inducing factor, mitochondria associated 1 multiple interactions
increases response to substance 		ISO Acetylcysteine inhibits the reaction [perfosfamide results in increased localization of AIFM1 protein]; perfosfamide results in increased expression of and results in increased localization of AIFM1 protein
AIFM1 results in increased susceptibility to perfosfamide 		CTD PMID:18034189 NCBI chr  X:132,528,107...132,567,237
Ensembl chr  X:132,528,107...132,567,237 		JBrowse link
G Akr1b10 aldo-keto reductase family 1 member B10 affects response to substance ISO AKR1B10 protein affects the susceptibility to perfosfamide CTD PMID:18473730 NCBI chr 4:64,005,632...64,027,860
Ensembl chr 4:64,007,420...64,020,847 		JBrowse link
G Aldh1a1 aldehyde dehydrogenase 1 family, member A1 decreases response to substance ISO ALDH1A1 protein results in decreased susceptibility to perfosfamide CTD PMID:8662658 PMID:16614850 NCBI chr 1:227,426,939...227,579,497
Ensembl chr 1:227,427,070...227,579,500 		JBrowse link
G Aldh1a2 aldehyde dehydrogenase 1 family, member A2 decreases response to substance ISO ALDH1A2 protein results in decreased susceptibility to perfosfamide CTD PMID:22079344 NCBI chr 8:80,758,641...80,837,891
Ensembl chr 8:80,758,142...80,837,883 		JBrowse link
G Aldh1b1 aldehyde dehydrogenase 1 family, member B1 affects response to substance ISO ALDH1B1 protein affects the susceptibility to perfosfamide CTD PMID:18473730 NCBI chr 5:64,859,000...64,864,008
Ensembl chr 5:64,858,934...64,864,365 		JBrowse link
G Aldh2 aldehyde dehydrogenase 2 family member decreases response to substance ISO ALDH2 protein results in decreased susceptibility to perfosfamide CTD PMID:22079344 NCBI chr12:40,610,244...40,643,220
Ensembl chr12:40,610,224...40,643,219 		JBrowse link
G Aldh3a1 aldehyde dehydrogenase 3 family, member A1 decreases response to substance ISO ALDH3A1 protein results in decreased susceptibility to perfosfamide CTD PMID:16614850 NCBI chr10:46,392,464...46,402,151
Ensembl chr10:46,392,411...46,402,151 		JBrowse link
G Apex1 apurinic/apyrimidinic endodeoxyribonuclease 1 decreases expression EXP perfosfamide results in decreased expression of APEX1 mRNA CTD PMID:11754170 NCBI chr15:26,618,146...26,620,330
Ensembl chr15:26,618,224...26,620,329 		JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions
increases expression
affects folding 		ISO Acetylcysteine inhibits the reaction [perfosfamide affects the folding of BAX protein]; Acetylcysteine inhibits the reaction [perfosfamide results in increased localization of BAX]; perfosfamide results in increased expression of and results in increased localization of BAX
perfosfamide results in increased expression of BAX
perfosfamide results in increased expression of BAX protein 		CTD PMID:16488414 PMID:18034189 NCBI chr 1:105,076,472...105,081,906
Ensembl chr 1:105,076,473...105,086,429 		JBrowse link
G Bbc3 Bcl-2 binding component 3 increases expression ISO perfosfamide results in increased expression of BBC3 mRNA CTD PMID:17068108 NCBI chr 1:86,141,450...86,150,666
Ensembl chr 1:86,141,603...86,150,666 		JBrowse link
G Bmpr1b bone morphogenetic protein receptor type 1B decreases expression ISO perfosfamide results in decreased expression of BMPR1B mRNA CTD PMID:19429390 NCBI chr 2:233,211,525...233,544,344
Ensembl chr 2:233,211,525...233,544,311 		JBrowse link
G C1d C1D nuclear receptor corepressor increases expression ISO perfosfamide results in increased expression of C1D mRNA CTD PMID:19429390 NCBI chr14:95,862,550...95,874,796
Ensembl chr14:95,861,978...95,874,796 		JBrowse link
G Casp3 caspase 3 increases activity
multiple interactions 		ISO perfosfamide results in increased activity of CASP3
perfosfamide promotes the reaction [TNF results in increased activity of CASP3 protein] 		CTD PMID:16488414 PMID:17434952 NCBI chr16:52,395,539...52,413,794
Ensembl chr16:52,395,540...52,413,732 		JBrowse link
G Casp9 caspase 9 increases activity ISO perfosfamide results in increased activity of CASP9 protein CTD PMID:16488414 Ensembl chr 5:159,391,188...159,409,648 JBrowse link
G Cdkn1a cyclin-dependent kinase inhibitor 1A increases expression ISO perfosfamide results in increased expression of CDKN1A
perfosfamide results in increased expression of CDKN1A mRNA; perfosfamide results in increased expression of CDKN1A protein 		CTD PMID:17068108 PMID:18034189 NCBI chr20:7,150,820...7,161,373
Ensembl chr20:7,153,958...7,164,969 		JBrowse link
G Cxcl9 C-X-C motif chemokine ligand 9 decreases expression ISO perfosfamide results in decreased expression of CXCL9 mRNA CTD PMID:19429390 NCBI chr14:16,007,166...16,012,077
Ensembl chr14:16,007,204...16,014,299 		JBrowse link
G E2f1 E2F transcription factor 1 increases expression ISO perfosfamide results in increased expression of E2F1 mRNA CTD PMID:19429390 NCBI chr 3:163,524,739...163,535,563
Ensembl chr 3:163,524,739...163,535,563 		JBrowse link
G Egr1 early growth response 1 decreases expression ISO perfosfamide results in decreased expression of EGR1 mRNA CTD PMID:19429390 NCBI chr18:26,737,078...26,740,877
Ensembl chr18:26,736,838...26,740,843 		JBrowse link
G Endog endonuclease G increases response to substance
multiple interactions 		ISO ENDOG results in increased susceptibility to perfosfamide
Acetylcysteine inhibits the reaction [perfosfamide results in increased localization of ENDOG protein]; perfosfamide results in increased expression of and results in increased localization of ENDOG protein 		CTD PMID:18034189 NCBI chr 3:33,846,935...33,849,531
Ensembl chr 3:33,846,885...33,849,573 		JBrowse link
G Epas1 endothelial PAS domain protein 1 increases expression ISO perfosfamide results in increased expression of EPAS1 protein CTD PMID:23251655 NCBI chr 6:13,543,252...13,626,147
Ensembl chr 6:13,544,389...13,624,729 		JBrowse link
G Epha6 Eph receptor A6 decreases expression ISO perfosfamide results in decreased expression of EPHA6 mRNA CTD PMID:19429390 NCBI chr11:53,226,784...54,178,120
Ensembl chr11:53,226,954...54,166,987 		JBrowse link
G Eya1 EYA transcriptional coactivator and phosphatase 1 decreases expression ISO perfosfamide results in decreased expression of EYA1 mRNA CTD PMID:19429390 NCBI chr 5:9,646,599...9,884,609
Ensembl chr 5:9,646,591...9,884,614 		JBrowse link
G Faslg Fas ligand increases expression ISO perfosfamide results in increased expression of FASLG mRNA; perfosfamide results in increased expression of FASLG protein CTD PMID:14760101 NCBI chr13:76,680,885...76,706,042
Ensembl chr13:76,688,243...76,695,503 		JBrowse link
G Foxf1 forkhead box F1 affects expression ISO perfosfamide affects the expression of FOXF1 mRNA CTD PMID:19429390 NCBI chr19:66,062,635...66,066,427
Ensembl chr19:66,062,369...66,066,428 		JBrowse link
G Gjc1 gap junction protein, gamma 1 increases expression ISO perfosfamide results in increased expression of GJC1 mRNA CTD PMID:19429390 NCBI chr10:88,262,840...88,285,646
Ensembl chr10:88,249,489...88,285,853 		JBrowse link
G Gli2 GLI family zinc finger 2 decreases expression ISO perfosfamide results in decreased expression of GLI2 mRNA CTD PMID:19429390 NCBI chr13:32,499,678...32,716,418
Ensembl chr13:32,499,678...32,716,418 		JBrowse link
G Hes1 hes family bHLH transcription factor 1 increases expression ISO perfosfamide results in increased expression of HES1 mRNA CTD PMID:19429390 NCBI chr11:84,210,632...84,213,045
Ensembl chr11:84,210,633...84,213,061 		JBrowse link
G Hif1a hypoxia inducible factor 1 subunit alpha increases expression ISO perfosfamide results in increased expression of HIF1A mRNA; perfosfamide results in increased expression of HIF1A protein CTD PMID:19429390 PMID:23251655 NCBI chr 6:98,357,788...98,405,068
Ensembl chr 6:98,359,910...98,405,323 		JBrowse link
G Hoxa11 homeobox A11 decreases expression ISO perfosfamide results in decreased expression of HOXA11 mRNA CTD PMID:19429390 NCBI chr 4:82,673,139...82,676,801
Ensembl chr 4:82,673,140...82,676,844 		JBrowse link
G Hoxa13 homeo box A13 increases expression ISO perfosfamide results in increased expression of HOXA13 mRNA CTD PMID:19429390 NCBI chr 4:82,689,566...82,691,701
Ensembl chr 4:82,689,566...82,691,701 		JBrowse link
G Hoxd10 homeo box D10 increases expression ISO perfosfamide results in increased expression of HOXD10 mRNA CTD PMID:19429390 NCBI chr 3:80,001,947...80,005,156
Ensembl chr 3:80,001,689...80,005,156 		JBrowse link
G Hras HRas proto-oncogene, GTPase decreases expression ISO perfosfamide results in decreased expression of HRAS mRNA CTD PMID:19429390 NCBI chr 1:205,712,625...205,729,406
Ensembl chr 1:205,725,975...205,729,590 		JBrowse link
G Kl Klotho decreases expression ISO perfosfamide results in decreased expression of KL mRNA CTD PMID:19429390 NCBI chr12:5,326,003...5,367,016
Ensembl chr12:5,325,959...5,367,015 		JBrowse link
G Lig3 DNA ligase 3 decreases expression EXP perfosfamide results in decreased expression of LIG3 mRNA CTD PMID:11754170 NCBI chr10:68,215,371...68,238,705
Ensembl chr10:68,215,407...68,238,704 		JBrowse link
G Mdm2 MDM2 proto-oncogene increases expression ISO perfosfamide results in increased expression of MDM2 CTD PMID:18034189 NCBI chr 7:55,176,558...55,201,757
Ensembl chr 7:55,176,560...55,200,791 		JBrowse link
G Mgmt O-6-methylguanine-DNA methyltransferase decreases expression EXP perfosfamide results in decreased expression of MGMT mRNA CTD PMID:11754170 NCBI chr 1:201,140,832...201,367,481
Ensembl chr 1:201,140,661...201,367,482 		JBrowse link
G Mlh1 mutL homolog 1 decreases expression EXP perfosfamide results in decreased expression of MLH1 mRNA CTD PMID:11754170 NCBI chr 8:120,074,871...120,112,109
Ensembl chr 8:120,065,900...120,112,011 		JBrowse link
G Mpg N-methylpurine-DNA glycosylase decreases expression EXP perfosfamide results in decreased expression of MPG mRNA CTD PMID:11754170 NCBI chr10:15,900,697...15,906,981
Ensembl chr10:15,899,635...15,907,052 		JBrowse link
G Mre11 MRE11 homolog, double strand break repair nuclease decreases expression EXP perfosfamide results in decreased expression of MRE11A mRNA CTD PMID:11754170 NCBI chr 8:19,900,211...19,961,906
Ensembl chr 8:19,913,772...19,961,904 		JBrowse link
G Myo1b myosin Ib increases expression ISO perfosfamide results in increased expression of MYO1B mRNA CTD PMID:19429390 NCBI chr 9:57,182,059...57,344,335
Ensembl chr 9:57,181,987...57,344,328 		JBrowse link
G Myog myogenin increases expression ISO perfosfamide results in increased expression of MYOG mRNA CTD PMID:19429390 NCBI chr13:48,297,476...48,300,065
Ensembl chr13:48,297,235...48,300,065 		JBrowse link
G Ndn necdin, MAGE family member increases expression ISO perfosfamide results in increased expression of NDN mRNA CTD PMID:19429390 NCBI chr 1:125,261,059...125,262,658
Ensembl chr 1:125,260,997...125,262,785 		JBrowse link
G Odc1 ornithine decarboxylase 1 decreases expression ISO perfosfamide results in decreased expression of ODC1 mRNA CTD PMID:19429390 NCBI chr 6:46,058,439...46,065,148
Ensembl chr 6:46,058,463...46,065,146 		JBrowse link
G Pea15 proliferation and apoptosis adaptor protein 15 decreases expression ISO perfosfamide results in decreased expression of PEA15 mRNA CTD PMID:19429390 NCBI chr13:87,190,189...87,199,811
Ensembl chr13:87,187,295...87,199,859 		JBrowse link
G Pmaip1 phorbol-12-myristate-13-acetate-induced protein 1 increases expression ISO perfosfamide results in increased expression of PMAIP1 mRNA CTD PMID:17068108 NCBI chr18:62,255,970...62,262,384
Ensembl chr18:62,255,598...62,262,382 		JBrowse link
G Pms1 PMS1 homolog 1, mismatch repair system component decreases expression EXP perfosfamide results in decreased expression of PMS1 mRNA CTD PMID:11754170 NCBI chr 9:55,721,393...55,832,225
Ensembl chr 9:55,745,374...55,832,221 		JBrowse link
G Pms2 PMS1 homolog 2, mismatch repair system component decreases expression EXP perfosfamide results in decreased expression of PMS2 mRNA CTD PMID:11754170 NCBI chr12:15,790,478...15,814,790
Ensembl chr12:15,790,478...15,815,248 		JBrowse link
G Polb DNA polymerase beta decreases expression EXP perfosfamide results in decreased expression of POLB mRNA CTD PMID:11754170 NCBI chr16:76,081,903...76,105,174
Ensembl chr16:76,081,864...76,108,180 		JBrowse link
G Pold1 DNA polymerase delta 1, catalytic subunit decreases expression ISO perfosfamide results in decreased expression of POLD1 mRNA CTD PMID:19429390 NCBI chr 1:104,161,984...104,178,074
Ensembl chr 1:104,162,016...104,172,982 		JBrowse link
G Rad21 RAD21 cohesin complex component decreases expression ISO perfosfamide results in decreased expression of RAD21 mRNA CTD PMID:19429390 NCBI chr 7:85,177,715...85,204,657
Ensembl chr 7:85,177,716...85,204,657 		JBrowse link
G Rad50 RAD50 double strand break repair protein decreases expression EXP perfosfamide results in decreased expression of RAD50 mRNA CTD PMID:11754170 NCBI chr10:38,310,147...38,362,100
Ensembl chr10:38,310,147...38,362,100 		JBrowse link
G Rad51 RAD51 recombinase decreases expression EXP perfosfamide results in decreased expression of RAD51 mRNA CTD PMID:11754170 NCBI chr 3:126,554,210...126,578,888
Ensembl chr 3:126,554,190...126,579,469 		JBrowse link
G Sdf4 stromal cell derived factor 4 decreases expression ISO perfosfamide results in decreased expression of SDF4 mRNA CTD PMID:19429390 NCBI chr 5:171,868,591...171,885,827
Ensembl chr 5:171,868,563...171,888,884 		JBrowse link
G Sfrp2 secreted frizzled-related protein 2 decreases expression ISO perfosfamide results in decreased expression of SFRP2 mRNA CTD PMID:19429390 NCBI chr 2:171,387,536...171,395,081
Ensembl chr 2:171,387,385...171,395,079 		JBrowse link
G Slc30a4 solute carrier family 30 member 4 decreases expression ISO perfosfamide results in decreased expression of SLC30A4 mRNA CTD PMID:19429390 NCBI chr 3:130,206,852...130,228,888
Ensembl chr 3:130,206,852...130,228,888 		JBrowse link
G Smad1 SMAD family member 1 decreases expression ISO perfosfamide results in decreased expression of SMAD1 mRNA CTD PMID:19429390 NCBI chr19:45,417,430...45,477,962
Ensembl chr19:45,417,433...45,477,957 		JBrowse link
G Tap1 transporter 1, ATP binding cassette subfamily B member affects response to substance ISO TAP1 protein affects the susceptibility to perfosfamide CTD PMID:18473730 NCBI chr20:4,658,171...4,668,543
Ensembl chr20:4,658,172...4,668,810 		JBrowse link
G Tcf12 transcription factor 12 increases expression ISO perfosfamide results in increased expression of TCF12 mRNA CTD PMID:19429390 NCBI chr 8:81,371,201...81,682,337
Ensembl chr 8:81,373,321...81,679,922 		JBrowse link
G Terc telomerase RNA component decreases expression ISO perfosfamide results in decreased expression of TERC mRNA CTD PMID:24571982 NCBI chr 2:114,744,148...114,744,535 JBrowse link
G Tert telomerase reverse transcriptase decreases expression ISO perfosfamide results in decreased expression of TERT mRNA CTD PMID:24571982 NCBI chr 1:31,465,766...31,488,650
Ensembl chr 1:31,466,056...31,488,111 		JBrowse link
G Tnf tumor necrosis factor multiple interactions ISO perfosfamide promotes the reaction [TNF results in increased activity of CASP3 protein] CTD PMID:16488414 NCBI chr20:3,626,685...3,629,303
Ensembl chr20:3,626,532...3,629,303 		JBrowse link
G Tp53 tumor protein p53 multiple interactions
increases expression 		ISO Acetylcysteine inhibits the reaction [perfosfamide results in increased expression of TP53]
perfosfamide results in increased expression of and results in increased phosphorylation of and results in increased activity of TRP53 protein 		CTD PMID:17068108 PMID:18034189 NCBI chr10:54,798,871...54,810,300
Ensembl chr10:54,798,851...54,810,299 		JBrowse link
G Trim27 tripartite motif-containing 27 decreases expression ISO perfosfamide results in decreased expression of TRIM27 mRNA CTD PMID:19429390 NCBI chr17:48,233,999...48,246,348
Ensembl chr17:48,234,002...48,246,348 		JBrowse link
G Ttf1 transcription termination factor 1 decreases expression ISO perfosfamide results in decreased expression of TTF1 mRNA CTD PMID:19429390 NCBI chr 3:32,782,544...32,807,202
Ensembl chr 3:32,782,308...32,807,201 		JBrowse link
G Ubb ubiquitin B decreases expression ISO perfosfamide results in decreased expression of UBB mRNA CTD PMID:19429390 NCBI chr10:47,746,923...47,748,628
Ensembl chr10:47,727,701...47,750,335 		JBrowse link
G Vegfa vascular endothelial growth factor A increases expression ISO perfosfamide results in increased expression of VEGFA mRNA CTD PMID:19429390 NCBI chr 9:22,452,854...22,468,194
Ensembl chr 9:22,439,392...22,468,194 		JBrowse link
G Vim vimentin decreases expression ISO perfosfamide results in decreased expression of VIM mRNA CTD PMID:19429390 NCBI chr17:81,577,261...81,585,746
Ensembl chr17:81,568,272...81,585,746 		JBrowse link
G Wnt11 Wnt family member 11 increases expression ISO perfosfamide results in increased expression of WNT11 mRNA CTD PMID:19429390 NCBI chr 1:162,545,660...162,565,456
Ensembl chr 1:162,545,680...162,564,660 		JBrowse link
G Xrcc1 X-ray repair cross complementing 1 decreases expression EXP perfosfamide results in decreased expression of XRCC1 mRNA CTD PMID:11754170 NCBI chr 1:89,268,721...89,296,619
Ensembl chr 1:89,268,644...89,296,613 		JBrowse link
G Xrcc5 X-ray repair cross complementing 5 decreases expression EXP perfosfamide results in decreased expression of XRCC5 mRNA CTD PMID:11754170 NCBI chr 9:81,404,507...81,493,293
Ensembl chr 9:81,375,863...81,493,293 		JBrowse link
G Ywhaz tyrosine 3-monooxygenase/tryptophan 5-monooxygenase activation protein, zeta decreases expression ISO perfosfamide results in decreased expression of YWHAZ mRNA CTD PMID:19429390 NCBI chr 7:69,826,404...69,848,702
Ensembl chr 7:69,826,404...69,849,007 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 20862
    role 20820
      biological role 20818
        biochemical role 20264
          metabolite 20245
            4-hydroperoxycyclophosphamide 74
Path 2
Term Annotations click to browse term
  CHEBI ontology 20862
    subatomic particle 20860
      composite particle 20860
        hadron 20860
          baryon 20860
            nucleon 20860
              atomic nucleus 20860
                atom 20860
                  main group element atom 20781
                    p-block element atom 20781
                      chalcogen 20491
                        oxygen atom 20457
                          oxygen molecular entity 20457
                            hydroxides 20230
                              oxoacid 19289
                                pnictogen oxoacid 15112
                                  phosphorus oxoacid 14667
                                    phosphoric acids 13987
                                      phosphoric acid 13987
                                        phosphoramide 1108
                                          phosphorodiamide 1057
                                            4-hydroperoxycyclophosphamide 74
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