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
Accession: CHEBI:196991
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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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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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