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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: Beilstein:531579;   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 3:10,041,820...10,145,076
Ensembl chr 3:10,041,826...10,144,388
JBrowse link
G Actb actin, beta decreases expression ISO perfosfamide results in decreased expression of ACTB mRNA CTD PMID:19429390 NCBI chr12:13,715,843...13,718,813
Ensembl chr12:13,715,843...13,718,841
JBrowse link
G Agt angiotensinogen decreases response to substance ISO AGT protein results in decreased susceptibility to perfosfamide CTD PMID:11034089 NCBI chr19:57,321,594...57,333,460
Ensembl chr19:57,321,640...57,333,433
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:135,304,063...135,343,062
Ensembl chr  X:135,304,066...135,343,087
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 4:61,813,265...61,830,371
Ensembl chr 4:61,771,970...61,828,657
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 1:238,222,689...238,264,381
Ensembl chr 1:238,222,521...238,264,330
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 8:77,640,234...77,719,488
Ensembl chr 8:77,640,222...77,719,489
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 5:61,382,351...61,387,359
Ensembl chr 5:61,382,351...61,387,358
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 chr12:40,466,418...40,498,813
Ensembl chr12:40,466,495...40,498,752
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 chr10:47,490,168...47,499,855
Ensembl chr10:47,490,153...47,499,876
JBrowse link
G Apex1 apurinic/apyrimidinic endodeoxyribonuclease 1 decreases expression EXP perfosfamide results in decreased expression of APEX1 mRNA CTD PMID:11754170 NCBI chr15:27,849,943...27,852,083
Ensembl chr15:27,849,979...27,852,082
JBrowse link
G Bax BCL2 associated X, apoptosis regulator multiple interactions
affects folding
increases expression
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 protein
CTD PMID:16488414, PMID:18034189 NCBI chr 1:101,451,801...101,457,207
Ensembl chr 1:101,451,802...101,457,207
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 1:78,261,491...78,267,802 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 2:247,392,195...247,662,026
Ensembl chr 2:247,403,920...247,446,882
JBrowse link
G C1d C1D nuclear receptor corepressor increases expression ISO perfosfamide results in increased expression of C1D mRNA CTD PMID:19429390 NCBI chr14:100,415,645...100,427,878
Ensembl chr14:100,415,668...100,427,260
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 chr16:48,845,011...48,863,249
Ensembl chr16:48,845,012...48,863,204
JBrowse link
G Casp9 caspase 9 increases activity ISO perfosfamide results in increased activity of CASP9 protein CTD PMID:16488414 NCBI chr 5:160,356,211...160,373,774
Ensembl chr 5:160,355,833...160,373,778
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 chr20:6,348,422...6,358,864
Ensembl chr20:6,351,458...6,358,864
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 chr14:17,228,832...17,233,743
Ensembl chr14:17,228,856...17,234,712
JBrowse link
G E2f1 E2F transcription factor 1 increases expression ISO perfosfamide results in increased expression of E2F1 mRNA CTD PMID:19429390 NCBI chr 3:150,062,895...150,073,721
Ensembl chr 3:150,047,826...150,073,721
JBrowse link
G Egr1 early growth response 1 decreases expression ISO perfosfamide results in decreased expression of EGR1 mRNA CTD PMID:19429390 NCBI chr18:27,657,903...27,660,101
Ensembl chr18:27,657,628...27,661,429
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 3:8,741,833...8,744,414
Ensembl chr 3:8,741,766...8,744,592
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 6:10,306,508...10,385,239
Ensembl chr 6:10,306,405...10,387,265
JBrowse link
G Epha6 Eph receptor A6 decreases expression ISO perfosfamide results in decreased expression of EPHA6 mRNA CTD PMID:19429390 NCBI chr11:41,867,607...42,843,800 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 5:4,275,728...4,495,525
Ensembl chr 5:4,373,626...4,513,142
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 chr13:79,696,811...79,717,581
Ensembl chr13:79,698,445...79,705,705
JBrowse link
G Foxf1 forkhead box F1 affects expression ISO perfosfamide affects the expression of FOXF1 mRNA CTD PMID:19429390 NCBI chr19:53,012,306...53,016,100
Ensembl chr19:53,012,332...53,016,086
JBrowse link
G Gjc1 gap junction protein, gamma 1 increases expression ISO perfosfamide results in increased expression of GJC1 mRNA CTD PMID:19429390 NCBI chr10:90,781,408...90,912,440
Ensembl chr10:90,781,402...90,912,287
JBrowse link
G Gli2 GLI family zinc finger 2 decreases expression ISO perfosfamide results in decreased expression of GLI2 mRNA CTD PMID:19429390 NCBI chr13:34,829,021...35,049,172
Ensembl chr13:34,829,139...35,048,444
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 chr11:74,312,837...74,315,249
Ensembl chr11:74,312,806...74,315,248
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 6:96,810,868...96,856,303
Ensembl chr 6:96,810,907...96,856,052
JBrowse link
G Hoxa11 homeobox A11 decreases expression ISO perfosfamide results in decreased expression of HOXA11 mRNA CTD PMID:19429390 NCBI chr 4:82,296,888...82,301,419
Ensembl chr 4:82,298,152...82,300,503
Ensembl chr 4:82,298,152...82,300,503
JBrowse link
G Hoxa13 homeo box A13 increases expression ISO perfosfamide results in increased expression of HOXA13 mRNA CTD PMID:19429390 Ensembl chr 4:82,228,017...82,229,397 JBrowse link
G Hoxd10 homeo box D10 increases expression ISO perfosfamide results in increased expression of HOXD10 mRNA CTD PMID:19429390 NCBI chr 3:61,614,133...61,617,342
Ensembl chr 3:61,613,774...61,617,367
JBrowse link
G Hras HRas proto-oncogene, GTPase decreases expression ISO perfosfamide results in decreased expression of HRAS mRNA CTD PMID:19429390 NCBI chr 1:214,178,404...214,181,841
Ensembl chr 1:214,178,407...214,181,686
JBrowse link
G Kl Klotho decreases expression ISO perfosfamide results in decreased expression of KL mRNA CTD PMID:19429390 NCBI chr12:942,974...987,206
Ensembl chr12:943,006...987,551
JBrowse link
G Lig3 DNA ligase 3 decreases expression EXP perfosfamide results in decreased expression of LIG3 mRNA CTD PMID:11754170 NCBI chr10:70,134,734...70,158,051
Ensembl chr10:70,134,729...70,158,055
JBrowse link
G Mdm2 MDM2 proto-oncogene increases expression ISO perfosfamide results in increased expression of MDM2 CTD PMID:18034189 NCBI chr 7:60,719,060...60,743,618
Ensembl chr 7:60,719,066...60,743,328
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 1:209,237,255...209,464,189
Ensembl chr 1:209,237,233...209,464,190
JBrowse link
G Mlh1 mutL homolog 1 decreases expression EXP perfosfamide results in decreased expression of MLH1 mRNA CTD PMID:11754170 NCBI chr 8:119,486,655...119,523,716
Ensembl chr 8:119,486,691...119,523,964
JBrowse link
G Mpg N-methylpurine-DNA glycosylase decreases expression EXP perfosfamide results in decreased expression of MPG mRNA CTD PMID:11754170 NCBI chr10:15,661,768...15,667,995
Ensembl chr10:15,661,608...15,668,022
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 8:13,304,355...13,350,329
Ensembl chr 8:13,305,152...13,352,489
JBrowse link
G Myo1b myosin Ib increases expression ISO perfosfamide results in increased expression of MYO1B mRNA CTD PMID:19429390 NCBI chr 9:54,706,005...54,766,054
Ensembl chr 9:54,558,202...54,766,054
JBrowse link
G Myog myogenin increases expression ISO perfosfamide results in increased expression of MYOG mRNA CTD PMID:19429390 NCBI chr13:51,126,459...51,129,048
Ensembl chr13:51,126,459...51,129,048
JBrowse link
G Ndn necdin, MAGE family member increases expression ISO perfosfamide results in increased expression of NDN mRNA CTD PMID:19429390 NCBI chr 1:122,981,755...122,983,354
Ensembl chr 1:122,981,755...122,983,351
JBrowse link
G Odc1 ornithine decarboxylase 1 decreases expression ISO perfosfamide results in decreased expression of ODC1 mRNA CTD PMID:19429390 NCBI chr 6:42,852,529...42,859,142
Ensembl chr 6:42,852,683...42,859,927
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 chr13:90,579,844...90,589,466
Ensembl chr13:90,579,846...90,589,466
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 chr18:62,159,128...62,179,635
Ensembl chr18:62,174,670...62,181,102
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 9:53,120,656...53,206,520
Ensembl chr 9:53,120,656...53,206,516
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 chr12:12,714,394...12,738,654
Ensembl chr12:12,714,394...12,738,641
JBrowse link
G Polb DNA polymerase beta decreases expression EXP perfosfamide results in decreased expression of POLB mRNA CTD PMID:11754170 NCBI chr16:74,237,001...74,260,272
Ensembl chr16:74,237,001...74,260,271
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 1:100,538,066...100,554,105
Ensembl chr 1:100,537,900...100,554,488
JBrowse link
G Rad21 RAD21 cohesin complex component decreases expression ISO perfosfamide results in decreased expression of RAD21 mRNA CTD PMID:19429390 NCBI chr 7:91,511,755...91,538,673
Ensembl chr 7:91,511,756...91,538,673
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 chr10:39,002,130...39,054,042
Ensembl chr10:39,001,498...39,054,142
JBrowse link
G Rad51 RAD51 recombinase decreases expression EXP perfosfamide results in decreased expression of RAD51 mRNA CTD PMID:11754170 NCBI chr 3:110,918,240...110,942,920
Ensembl chr 3:110,918,243...110,942,917
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 5:173,425,922...173,444,478
Ensembl chr 5:173,425,907...173,444,620
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 2:182,723,732...182,731,277
Ensembl chr 2:182,723,854...182,731,764
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 3:114,805,919...114,828,154
Ensembl chr 3:114,805,922...114,828,154
JBrowse link
G Smad1 SMAD family member 1 decreases expression ISO perfosfamide results in decreased expression of SMAD1 mRNA CTD PMID:19429390 NCBI chr19:32,182,942...32,248,694
Ensembl chr19:32,188,267...32,248,684
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 chr20:3,979,302...3,989,669
Ensembl chr20:3,979,035...3,989,669
JBrowse link
G Tcf12 transcription factor 12 increases expression ISO perfosfamide results in increased expression of TCF12 mRNA CTD PMID:19429390 NCBI chr 8:78,343,634...78,657,738
Ensembl chr 8:78,345,754...78,655,856
JBrowse link
G Terc telomerase RNA component decreases expression ISO perfosfamide results in decreased expression of TERC mRNA CTD PMID:24571982 NCBI chr 2:116,432,723...116,433,110
Ensembl chr 2:116,432,691...116,433,110
JBrowse link
G Tert telomerase reverse transcriptase decreases expression ISO perfosfamide results in decreased expression of TERT mRNA CTD PMID:24571982 NCBI chr 1:32,250,876...32,275,330
Ensembl chr 1:32,251,714...32,272,476
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 chr20:5,189,382...5,192,000
Ensembl chr20:5,189,390...5,192,000
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 chr10:56,186,299...56,198,449
Ensembl chr10:56,187,020...56,198,449
JBrowse link
G Trim27 tripartite motif-containing 27 decreases expression ISO perfosfamide results in decreased expression of TRIM27 mRNA CTD PMID:19429390 NCBI chr17:45,613,863...45,626,212
Ensembl chr17:45,613,864...45,626,212
JBrowse link
G Ttf1 transcription termination factor 1 decreases expression ISO perfosfamide results in decreased expression of TTF1 mRNA CTD PMID:19429390 NCBI chr 3:7,635,630...7,660,153
Ensembl chr 3:7,635,933...7,660,673
JBrowse link
G Ubb ubiquitin B decreases expression ISO perfosfamide results in decreased expression of UBB mRNA CTD PMID:19429390 NCBI chr10:48,880,231...48,881,896
Ensembl chr10:48,881,049...48,881,881
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 9:17,340,341...17,355,681
Ensembl chr 9:17,340,341...17,355,681
JBrowse link
G Vim vimentin decreases expression ISO perfosfamide results in decreased expression of VIM mRNA CTD PMID:19429390 NCBI chr17:80,882,715...80,891,200
Ensembl chr17:80,882,666...80,891,212
JBrowse link
G Wnt11 Wnt family member 11 increases expression ISO perfosfamide results in increased expression of WNT11 mRNA CTD PMID:19429390 NCBI chr 1:163,794,136...163,813,756
Ensembl chr 1:163,797,660...163,813,756
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 1:81,412,635...81,441,680
Ensembl chr 1:81,413,353...81,441,678
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 9:79,659,275...79,748,050
Ensembl chr 9:79,659,251...79,748,078
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 7:75,573,553...75,598,295
Ensembl chr 7:75,574,967...75,597,276
JBrowse link

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Term Annotations click to browse term
  CHEBI ontology 19816
    role 19764
      biological role 19764
        biochemical role 19313
          metabolite 19294
            4-hydroperoxycyclophosphamide 74
Path 2
Term Annotations click to browse term
  CHEBI ontology 19816
    subatomic particle 19814
      composite particle 19814
        hadron 19814
          baryon 19814
            nucleon 19814
              atomic nucleus 19814
                atom 19814
                  main group element atom 19702
                    p-block element atom 19702
                      chalcogen 19399
                        oxygen atom 19361
                          oxygen molecular entity 19361
                            hydroxides 19107
                              oxoacid 18241
                                pnictogen oxoacid 10179
                                  phosphorus oxoacid 9071
                                    phosphoric acids 7830
                                      phosphoric acid 7830
                                        phosphoramide 1008
                                          phosphorodiamide 975
                                            4-hydroperoxycyclophosphamide 74
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.