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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-hydroxy-PhIP
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Accession:CHEBI:133920 term browser browse the term
Definition:An imidazopyridine that is 1H--imidazo[4,5-b]pyridine which is substituted at positions 1, 2, and 6 by methyl, hydoxyamino, and phenyl groups, respectively. The active metabolite of the dietary carcinogen PhIP.
Synonyms:exact_synonym: N-(1-methyl-6-phenyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ylidene)hydroxylamine
 related_synonym: 2-Hydroxyamino-PhIP;   2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine;   Formula=C13H12N4O;   InChI=1S/C13H12N4O/c1-17-11-7-10(9-5-3-2-4-6-9)8-14-12(11)15-13(17)16-18/h2-8,18H,1H3,(H,14,15,16);   InChIKey=DCVWQAGUQFBCTF-UHFFFAOYSA-N;   N-OH-PhIP;   SMILES=CN1C=2C=C(C=NC2N=C1NO)C3=CC=CC=C3
 xref: CAS:124489-20-9;   ChemIDplus:94711;   KEGG:C20286
 xref_mesh: MESH:C060533
 xref: PMID:10357796;   PMID:10837010;   PMID:11196146;   PMID:11408353;   PMID:11442279;   PMID:11700987;   PMID:11834212;   PMID:12175520;   PMID:12473729;   PMID:12773763;   PMID:15310245;   PMID:16137733;   PMID:17122891;   PMID:17638922;   PMID:20708442;   PMID:2233839;   PMID:24334255;   PMID:24718704;   PMID:25815793;   PMID:26270892;   PMID:27032077;   PMID:27984695;   PMID:7728954;   PMID:7852185;   PMID:8142010;   PMID:8199311;   PMID:8600367;   PMID:9760588;   Reaxys:8393164


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N-hydroxy-PhIP term browser
Symbol Object Name Qualifiers Evidence Notes Source PubMed Reference(s) RGD Reference(s) Position
G Abcb1a ATP binding cassette subfamily B member 1A multiple interactions ISO [ABCB1A protein affects the metabolism of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine] which results in increased abundance of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine CTD PMID:30701287 NCBI chr 4:22,339,829...22,517,642
Ensembl chr 4:22,133,521...22,425,515
JBrowse link
G Abcb1b ATP-binding cassette, subfamily B (MDR/TAP), member 1B multiple interactions ISO [ABCB1B protein affects the metabolism of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine] which results in increased abundance of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine CTD PMID:30701287 NCBI chr 4:22,225,123...22,307,577
Ensembl chr 4:22,133,521...22,425,515
JBrowse link
G Abcc2 ATP binding cassette subfamily C member 2 multiple interactions ISO [ABCC2 protein affects the metabolism of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine] which results in increased abundance of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine CTD PMID:30701287 NCBI chr 1:263,554,426...263,612,556
Ensembl chr 1:263,554,453...263,613,252
JBrowse link
G Abcc3 ATP binding cassette subfamily C member 3 multiple interactions ISO [ABCC3 protein affects the metabolism of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine] which results in increased abundance of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine CTD PMID:30701287 NCBI chr10:82,047,308...82,116,928
Ensembl chr10:82,047,863...82,117,109
JBrowse link
G Abcg2 ATP binding cassette subfamily G member 2 affects transport
multiple interactions
ISO ABCG2 protein affects the transport of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
[ABCG2 protein affects the metabolism of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine] which results in increased abundance of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
CTD PMID:18322075, PMID:30701287 NCBI chr 4:88,765,441...88,890,268
Ensembl chr 4:88,832,178...88,890,621
JBrowse link
G Cyp1a1 cytochrome P450, family 1, subfamily a, polypeptide 1 multiple interactions ISO [CYP1A1 protein results in increased hydroxylation of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine] which results in increased chemical synthesis of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine; [Tetrachlorodibenzodioxin results in increased activity of CYP1A1 protein] which results in increased chemical synthesis of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
[[CYP1A2 protein co-treated with CYP1A1 protein] results in increased hydroxylation of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine] which results in increased chemical synthesis of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine; [CYP1A1 protein results in increased metabolism of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine] which results in increased chemical synthesis of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
CTD PMID:16167840, PMID:17052995, PMID:17279779 NCBI chr 8:62,472,087...62,478,122
Ensembl chr 8:62,472,095...62,478,147
JBrowse link
G Cyp1a2 cytochrome P450, family 1, subfamily a, polypeptide 2 multiple interactions ISO [[CYP1A2 protein co-treated with CYP1A1 protein] results in increased hydroxylation of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine] which results in increased chemical synthesis of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine; [CYP1A2 protein results in increased metabolism of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine] which results in increased chemical synthesis of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine; [CYP1A2 protein results in increased metabolism of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine] which results in increased chemical synthesis of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine metabolite
[CYP1A2 protein results in increased metabolism of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine] which results in increased abundance of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
CTD PMID:1943715, PMID:16167840, PMID:17279779, PMID:20192249 NCBI chr 8:62,451,360...62,458,244
Ensembl chr 8:62,451,329...62,458,301
JBrowse link
G Cyp1b1 cytochrome P450, family 1, subfamily b, polypeptide 1 multiple interactions ISO [CYP1B1 protein results in increased metabolism of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine] which results in increased chemical synthesis of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine CTD PMID:17279779 NCBI chr 6:2,308,179...2,316,739
Ensembl chr 6:2,307,808...2,316,722
JBrowse link
G Cyp2c6v1 cytochrome P450, family 2, subfamily C, polypeptide 6, variant 1 multiple interactions ISO [CYP2C19 protein results in increased metabolism of 2-amino-1-methyl-6-phenylimidazo(4,5-b)pyridine] which results in increased chemical synthesis of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine CTD PMID:17279779 NCBI chr 1:147,713,879...147,814,410
Ensembl chr 1:147,713,892...147,888,007
JBrowse link
G Esr1 estrogen receptor 1 multiple interactions
decreases activity
ISO 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine inhibits the reaction [Estradiol results in increased activity of ESR1 protein]
2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine results in decreased activity of ESR1 protein
CTD PMID:16533016 NCBI chr 1:41,192,029...41,594,799
Ensembl chr 1:41,192,824...41,594,796
JBrowse link
G Gsta1 glutathione S-transferase alpha 1 increases expression EXP 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine results in increased expression of GSTA1 protein CTD PMID:17122891 NCBI chr 9:27,366,404...27,381,004
Ensembl chr 9:27,368,272...27,452,902
JBrowse link
G Gsta2 glutathione S-transferase alpha 2 increases expression EXP 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine results in increased expression of GSTA3 protein CTD PMID:17122891 NCBI chr 8:85,640,081...85,645,621 JBrowse link
G Gsta4 glutathione S-transferase alpha 4 increases expression EXP 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine results in increased expression of GSTA4 protein CTD PMID:17122891 NCBI chr 8:85,497,557...85,514,732
Ensembl chr 8:85,497,557...85,518,879
JBrowse link
G Gstm1 glutathione S-transferase mu 1 increases expression EXP 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine results in increased expression of GSTM1 protein CTD PMID:17122891 NCBI chr 2:210,803,869...210,809,461
Ensembl chr 2:210,803,869...210,809,306
JBrowse link
G Gstp1 glutathione S-transferase pi 1 multiple interactions
increases expression
decreases response to substance
ISO
EXP
[GSTP1 protein co-treated with Glutathione] inhibits the reaction [[Adenosine Triphosphate results in increased metabolism of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine] which results in increased abundance of 2-amino-1-methyl-6-phenolimidazo(4,5-b)pyridine-DNA adduct]; [GSTP1 protein co-treated with Glutathione] inhibits the reaction [Adenosine Triphosphate results in increased activity of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine]
2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine results in increased expression of GSTP1 protein
GSTP1 protein results in decreased susceptibility to 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
CTD PMID:11196146, PMID:17122891 NCBI chr 1:219,291,679...219,294,147
Ensembl chr 1:219,291,679...219,294,147
JBrowse link
G Nat1 N-acetyltransferase 1 multiple interactions
increases metabolic processing
ISO NAT1 protein affects the acetylation of and affects the activity of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
NAT1 protein results in increased metabolism of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
CTD PMID:11505221, PMID:29596660 NCBI chr16:23,970,742...23,991,573
Ensembl chr16:23,970,743...23,991,573
JBrowse link
G Nat2 N-acetyltransferase 2 multiple interactions
increases metabolic processing
increases acetylation
EXP
ISO
4-biphenylamine inhibits the reaction [NAT2 protein results in increased acetylation of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine]
NAT2 protein results in increased metabolism of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
CTD PMID:12222688, PMID:18842621, PMID:29596660 NCBI chr16:23,960,709...23,991,570
Ensembl chr16:23,961,067...23,991,570
JBrowse link
G Pdia3 protein disulfide isomerase family A, member 3 affects expression
multiple interactions
EXP 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine affects the expression of PDIA3 protein
[2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine co-treated with Dihydrotestosterone] affects the expression of PDIA3 protein
CTD PMID:19639176 NCBI chr 3:113,376,983...113,400,707
Ensembl chr 3:113,376,983...113,400,707
JBrowse link
G Rab7a RAB7A, member RAS oncogene family affects expression
multiple interactions
EXP 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine affects the expression of RAB7A protein
[2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine co-treated with Dihydrotestosterone] affects the expression of RAB7A protein
CTD PMID:19639176 NCBI chr 4:119,910,461...119,963,065
Ensembl chr 4:119,910,478...119,959,173
JBrowse link
G Rps7 ribosomal protein S7 multiple interactions
affects expression
EXP [2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine co-treated with Dihydrotestosterone] affects the expression of RPS7 protein
2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine affects the expression of RPS7 protein
CTD PMID:19639176 NCBI chr 6:47,899,525...47,904,389
Ensembl chr 6:47,899,525...47,904,437
JBrowse link
G Sar1a secretion associated, Ras related GTPase 1A affects expression
multiple interactions
EXP 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine affects the expression of SAR1A protein
[2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine co-treated with Dihydrotestosterone] affects the expression of SAR1A protein
CTD PMID:19639176 NCBI chr20:31,298,269...31,310,676
Ensembl chr20:31,265,483...31,310,674
JBrowse link
G Sult1a1 sulfotransferase family 1A member 1 multiple interactions
increases metabolic processing
ISO SULT1A1 protein results in increased metabolism of and results in increased activity of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
SULT1A1 protein results in increased metabolism of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
CTD PMID:12067565, PMID:29596660 NCBI chr 1:198,100,586...198,104,106
Ensembl chr 1:198,100,586...198,104,109
JBrowse link
G Ugt1a1 UDP glucuronosyltransferase family 1 member A1 multiple interactions
affects metabolic processing
increases metabolic processing
increases glucuronidation
ISO UGT1A1 promoter polymorphism affects the reaction [2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine binds to Glucuronides]; UGT1A1 protein promotes the reaction [2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine binds to Glucuronides]; UGT1A1 protein results in increased glucuronidation of and results in decreased activity of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
UGT1A1 promoter polymorphism affects the metabolism of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
UGT1A1 protein results in increased metabolism of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
UGT1A1 protein results in increased glucuronidation of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
CTD PMID:11442279, PMID:15310245, PMID:15769885, PMID:15986396 NCBI chr 9:95,295,701...95,302,822
Ensembl chr 9:95,161,157...95,302,822
JBrowse link
G Ugt1a2 UDP glucuronosyltransferase 1 family, polypeptide A2 increases glucuronidation ISO UGT1A3 protein results in increased glucuronidation of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine CTD PMID:15310245 NCBI chr 9:95,285,592...95,302,822
Ensembl chr 9:95,161,157...95,302,822
JBrowse link
G Ugt1a5 UDP glucuronosyltransferase family 1 member A5 increases metabolic processing
increases glucuronidation
multiple interactions
ISO UGT1A4 protein results in increased metabolism of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
UGT1A4 protein results in increased glucuronidation of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
UGT1A4 protein promotes the reaction [2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine binds to Glucuronides]
CTD PMID:15310245, PMID:15986396 NCBI chr 9:95,256,628...95,302,822
Ensembl chr 9:95,161,157...95,302,822
JBrowse link
G Ugt1a8 UDP glucuronosyltransferase family 1 member A8 increases glucuronidation
multiple interactions
increases metabolic processing
ISO UGT1A8 protein results in increased glucuronidation of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
UGT1A8 protein promotes the reaction [2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine binds to Glucuronides]
UGT1A8 protein results in increased metabolism of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
CTD PMID:15310245, PMID:15986396 NCBI chr 9:95,221,474...95,302,822
Ensembl chr 9:95,161,157...95,302,822
JBrowse link
G Ugt1a9 UDP glucuronosyltransferase family 1 member A9 multiple interactions
increases glucuronidation
increases metabolic processing
ISO UGT1A9 protein promotes the reaction [2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine binds to Glucuronides]
UGT1A9 protein results in increased glucuronidation of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
UGT1A9 protein results in increased metabolism of 2-hydroxyamino-1-methyl-6-phenylimidazo(4,5-b)pyridine
CTD PMID:11375903, PMID:15310245, PMID:15986396 NCBI chr 9:95,161,157...95,302,822
Ensembl chr 9:95,161,157...95,302,822
JBrowse link

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  CHEBI ontology 19770
    role 19718
      biological role 19717
        aetiopathogenetic role 18843
          genotoxin 16949
            N-hydroxy-PhIP 26
Path 2
Term Annotations click to browse term
  CHEBI ontology 19770
    subatomic particle 19768
      composite particle 19768
        hadron 19768
          baryon 19768
            nucleon 19768
              atomic nucleus 19768
                atom 19768
                  main group element atom 19655
                    main group molecular entity 19655
                      s-block molecular entity 19397
                        hydrogen molecular entity 19387
                          hydrides 18419
                            inorganic hydride 17380
                              pnictogen hydride 17349
                                nitrogen hydride 17216
                                  azane 16932
                                    ammonia 16931
                                      organic amino compound 16930
                                        primary amino compound 7845
                                          PhIP 577
                                            N-hydroxy-PhIP 26
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RGD is funded by grant HL64541 from the National Heart, Lung, and Blood Institute on behalf of the NIH.