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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 3:14,979,853...15,083,065
Ensembl chr 3:14,979,853...15,083,065 		JBrowse link
G Actb actin, beta decreases expression ISO perfosfamide results in decreased expression of ACTB mRNA CTD PMID:19429390 NCBI chr12:11,663,112...11,666,697
Ensembl chr12:11,663,109...11,672,877 		JBrowse link
G Agt angiotensinogen decreases response to substance ISO AGT protein results in decreased susceptibility to perfosfamide CTD PMID:11034089 NCBI chr19:52,529,139...52,549,618
Ensembl chr19:52,529,185...52,540,977 		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:127,650,223...127,689,356
Ensembl chr  X:127,650,226...127,689,256 		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 4:63,038,459...63,060,336
Ensembl chr 4:63,040,169...63,053,852 		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 1:218,000,470...218,152,962
Ensembl chr 1:218,042,127...218,152,961 		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 8:71,877,850...71,957,107
Ensembl chr 8:71,877,850...71,957,107 		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 5:60,063,370...60,068,378
Ensembl chr 5:60,063,225...60,068,378 		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 chr12:34,949,549...34,982,527 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 chr10:45,892,993...45,902,680
Ensembl chr10:45,892,924...45,902,681 		JBrowse link
G Apex1 apurinic/apyrimidinic endodeoxyribonuclease 1 decreases expression EXP perfosfamide results in decreased expression of APEX1 mRNA CTD PMID:11754170 NCBI chr15:24,144,595...24,146,785
Ensembl chr15:24,144,362...24,146,785 		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 1:95,940,001...95,945,407
Ensembl chr 1:95,938,808...95,945,368 		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 1:77,013,281...77,022,509
Ensembl chr 1:77,014,543...77,022,509 		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 2:230,538,252...230,871,077
Ensembl chr 2:230,541,558...230,871,368 		JBrowse link
G C1d C1D nuclear receptor corepressor increases expression ISO perfosfamide results in increased expression of C1D mRNA CTD PMID:19429390 NCBI chr14:91,660,951...91,673,177
Ensembl chr14:91,660,989...91,672,852 		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 chr16:45,662,910...45,681,171
Ensembl chr16:45,662,910...45,684,648 		JBrowse link
G Casp9 caspase 9 increases activity ISO perfosfamide results in increased activity of CASP9 protein CTD PMID:16488414 NCBI chr 5:154,108,872...154,126,628
Ensembl chr 5:154,109,046...154,126,626 		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 chr20:7,149,177...7,159,727
Ensembl chr20:7,149,217...7,159,585 		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 chr14:15,722,868...15,727,779
Ensembl chr14:15,722,908...15,728,435 		JBrowse link
G E2f1 E2F transcription factor 1 increases expression ISO perfosfamide results in increased expression of E2F1 mRNA CTD PMID:19429390 NCBI chr 3:143,064,535...143,075,362 JBrowse link
G Egr1 early growth response 1 decreases expression ISO perfosfamide results in decreased expression of EGR1 mRNA CTD PMID:19429390 NCBI chr18:26,463,333...26,465,531
Ensembl chr18:26,462,981...26,466,766 		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 3:13,449,113...13,451,715
Ensembl chr 3:13,449,086...13,451,932 		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 6:7,790,236...7,871,246
Ensembl chr 6:7,790,647...7,871,228 		JBrowse link
G Epha6 Eph receptor A6 decreases expression ISO perfosfamide results in decreased expression of EPHA6 mRNA CTD PMID:19429390 NCBI chr11:39,757,870...40,708,901 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 5:4,863,501...5,101,483
Ensembl chr 5:4,955,543...5,101,483 		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 chr13:74,151,519...74,172,760
Ensembl chr13:74,154,954...74,162,215 		JBrowse link
G Foxf1 forkhead box F1 affects expression ISO perfosfamide affects the expression of FOXF1 mRNA CTD PMID:19429390 NCBI chr19:49,153,729...49,157,741
Ensembl chr19:49,153,699...49,157,738 		JBrowse link
G Gjc1 gap junction protein, gamma 1 increases expression ISO perfosfamide results in increased expression of GJC1 mRNA CTD PMID:19429390 NCBI chr10:87,758,192...87,785,443
Ensembl chr10:87,760,528...87,785,867 		JBrowse link
G Gli2 GLI family zinc finger 2 decreases expression ISO perfosfamide results in decreased expression of GLI2 mRNA CTD PMID:19429390 NCBI chr13:29,946,809...30,163,901
Ensembl chr13:29,946,809...30,163,574 		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 chr11:70,705,763...70,708,176
Ensembl chr11:70,705,764...70,708,192 		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 6:92,624,059...92,669,262
Ensembl chr 6:92,624,390...92,669,261 		JBrowse link
G Hoxa11 homeobox A11 decreases expression ISO perfosfamide results in decreased expression of HOXA11 mRNA CTD PMID:19429390 NCBI chr 4:81,342,527...81,346,189
Ensembl chr 4:81,342,528...81,346,232 		JBrowse link
G Hoxa13 homeo box A13 increases expression ISO perfosfamide results in increased expression of HOXA13 mRNA CTD PMID:19429390 NCBI chr 4:81,358,956...81,361,091
Ensembl chr 4:81,358,956...81,361,091 		JBrowse link
G Hoxd10 homeo box D10 increases expression ISO perfosfamide results in increased expression of HOXD10 mRNA CTD PMID:19429390 NCBI chr 3:59,594,516...59,597,725
Ensembl chr 3:59,594,516...59,597,725 		JBrowse link
G Hras HRas proto-oncogene, GTPase decreases expression ISO perfosfamide results in decreased expression of HRAS mRNA CTD PMID:19429390 NCBI chr 1:196,290,127...196,299,823
Ensembl chr 1:196,296,263...196,300,615 		JBrowse link
G Kl Klotho decreases expression ISO perfosfamide results in decreased expression of KL mRNA CTD PMID:19429390 NCBI chr12:490,402...531,417
Ensembl chr12:490,399...530,080 		JBrowse link
G Lig3 DNA ligase 3 decreases expression EXP perfosfamide results in decreased expression of LIG3 mRNA CTD PMID:11754170 NCBI chr10:67,717,796...67,741,141
Ensembl chr10:67,717,812...67,798,414 		JBrowse link
G Mdm2 MDM2 proto-oncogene increases expression ISO perfosfamide results in increased expression of MDM2 CTD PMID:18034189 NCBI chr 7:53,290,660...53,315,205
Ensembl chr 7:53,290,664...53,314,915 		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 1:191,710,980...191,937,760
Ensembl chr 1:191,710,930...191,937,756 		JBrowse link
G Mlh1 mutL homolog 1 decreases expression EXP perfosfamide results in decreased expression of MLH1 mRNA CTD PMID:11754170 NCBI chr 8:111,196,468...111,233,721
Ensembl chr 8:111,196,468...111,233,617 		JBrowse link
G Mpg N-methylpurine-DNA glycosylase decreases expression EXP perfosfamide results in decreased expression of MPG mRNA CTD PMID:11754170 NCBI chr10:15,396,246...15,402,528
Ensembl chr10:15,395,782...15,402,520 		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 8:11,618,876...11,680,451
Ensembl chr 8:11,632,354...11,678,279 		JBrowse link
G Myo1b myosin Ib increases expression ISO perfosfamide results in increased expression of MYO1B mRNA CTD PMID:19429390 NCBI chr 9:49,690,043...49,852,373
Ensembl chr 9:49,690,086...49,850,798 		JBrowse link
G Myog myogenin increases expression ISO perfosfamide results in increased expression of MYOG mRNA CTD PMID:19429390 NCBI chr13:45,745,455...45,748,044
Ensembl chr13:45,745,436...45,748,039 		JBrowse link
G Ndn necdin, MAGE family member increases expression ISO perfosfamide results in increased expression of NDN mRNA CTD PMID:19429390 NCBI chr 1:115,849,168...115,850,767
Ensembl chr 1:115,849,105...115,850,767 		JBrowse link
G Odc1 ornithine decarboxylase 1 decreases expression ISO perfosfamide results in decreased expression of ODC1 mRNA CTD PMID:19429390 NCBI chr 6:40,329,831...40,336,444
Ensembl chr 6:40,329,964...40,336,440 		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 chr13:84,657,815...84,667,437
Ensembl chr13:84,654,870...84,667,499 		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 chr18:59,986,187...59,990,174
Ensembl chr18:59,986,017...59,992,429 		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 9:48,229,403...48,340,237
Ensembl chr 9:48,253,410...48,340,237 		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 chr12:10,676,819...10,701,161
Ensembl chr12:10,676,764...10,701,066 		JBrowse link
G Polb DNA polymerase beta decreases expression EXP perfosfamide results in decreased expression of POLB mRNA CTD PMID:11754170 NCBI chr16:69,379,438...69,402,710
Ensembl chr16:69,379,400...69,404,812 		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 1:95,025,462...95,041,559
Ensembl chr 1:95,025,499...95,036,465 		JBrowse link
G Rad21 RAD21 cohesin complex component decreases expression ISO perfosfamide results in decreased expression of RAD21 mRNA CTD PMID:19429390 NCBI chr 7:83,287,867...83,314,810
Ensembl chr 7:83,287,870...83,314,817 		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 chr10:37,809,353...37,861,309
Ensembl chr10:37,808,726...37,861,396 		JBrowse link
G Rad51 RAD51 recombinase decreases expression EXP perfosfamide results in decreased expression of RAD51 mRNA CTD PMID:11754170 NCBI chr 3:106,099,753...106,125,038
Ensembl chr 3:106,100,381...106,125,035 		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 5:166,586,581...166,606,661
Ensembl chr 5:166,586,390...166,604,521 		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 2:169,089,517...169,097,064
Ensembl chr 2:169,089,517...169,097,063 		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 3:109,753,270...109,775,306
Ensembl chr 3:109,753,273...109,775,306 		JBrowse link
G Smad1 SMAD family member 1 decreases expression ISO perfosfamide results in decreased expression of SMAD1 mRNA CTD PMID:19429390 NCBI chr19:28,513,130...28,573,665
Ensembl chr19:28,513,131...28,573,651 		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 chr20:4,656,262...4,666,634
Ensembl chr20:4,656,263...4,666,901 		JBrowse link
G Tcf12 transcription factor 12 increases expression ISO perfosfamide results in increased expression of TCF12 mRNA CTD PMID:19429390 NCBI chr 8:72,490,447...72,799,265
Ensembl chr 8:72,492,567...72,799,201 		JBrowse link
G Terc telomerase RNA component decreases expression ISO perfosfamide results in decreased expression of TERC mRNA CTD PMID:24571982 NCBI chr 2:112,815,654...112,816,041 JBrowse link
G Tert telomerase reverse transcriptase decreases expression ISO perfosfamide results in decreased expression of TERT mRNA CTD PMID:24571982 NCBI chr 1:29,637,213...29,659,509
Ensembl chr 1:29,637,506...29,659,561 		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 chr20:3,622,011...3,624,629
Ensembl chr20:3,622,011...3,624,629 		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 chr10:54,300,070...54,311,525
Ensembl chr10:54,300,048...54,311,524 		JBrowse link
G Trim27 tripartite motif-containing 27 decreases expression ISO perfosfamide results in decreased expression of TRIM27 mRNA CTD PMID:19429390 NCBI chr17:43,538,282...43,550,633
Ensembl chr17:43,538,285...43,550,643 		JBrowse link
G Ttf1 transcription termination factor 1 decreases expression ISO perfosfamide results in decreased expression of TTF1 mRNA CTD PMID:19429390 NCBI chr 3:12,384,626...12,409,257
Ensembl chr 3:12,384,655...12,409,257 		JBrowse link
G Ubb ubiquitin B decreases expression ISO perfosfamide results in decreased expression of UBB mRNA CTD PMID:19429390 NCBI chr10:47,247,629...47,249,335
Ensembl chr10:47,245,637...47,249,333 		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 9:14,955,300...14,970,641
Ensembl chr 9:14,955,300...14,970,641 		JBrowse link
G Vim vimentin decreases expression ISO perfosfamide results in decreased expression of VIM mRNA CTD PMID:19429390 NCBI chr17:76,668,701...76,677,186
Ensembl chr17:76,668,647...76,677,187 		JBrowse link
G Wnt11 Wnt family member 11 increases expression ISO perfosfamide results in increased expression of WNT11 mRNA CTD PMID:19429390 NCBI chr 1:153,134,503...153,154,294
Ensembl chr 1:153,138,197...153,154,294 		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 1:80,140,495...80,168,705
Ensembl chr 1:80,141,207...80,168,701 		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 9:73,955,220...74,044,020
Ensembl chr 9:73,955,216...74,044,018 		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 7:67,941,353...67,963,651
Ensembl chr 7:67,940,017...67,963,668 		JBrowse link
Term paths to the root
Path 1
Term Annotations click to browse term
  CHEBI ontology 19812
    role 19761
      biological role 19761
        biochemical role 19381
          metabolite 19356
            4-hydroperoxycyclophosphamide 74
Path 2
Term Annotations click to browse term
  CHEBI ontology 19812
    subatomic particle 19811
      composite particle 19811
        hadron 19811
          baryon 19811
            nucleon 19811
              atomic nucleus 19811
                atom 19811
                  main group element atom 19708
                    p-block element atom 19708
                      chalcogen 19460
                        oxygen atom 19436
                          oxygen molecular entity 19436
                            hydroxides 19175
                              oxoacid 18488
                                pnictogen oxoacid 10688
                                  phosphorus oxoacid 9669
                                    phosphoric acids 8466
                                      phosphoric acid 8466
                                        phosphoramide 1016
                                          phosphorodiamide 983
                                            4-hydroperoxycyclophosphamide 74
paths to the root