ADH7
O2
CYP4V2
CHOL
SMOX-3
H+
4OH-9cRA
CYP4F3
TAM
NADP+
H+
PREG
12OH-DDCX
CYP4A11
H+
O2
ABPH
H2O2
NADPH
H+
O2
NADP+
CYP2E1
H2O
CYP4B1
CH3CHO
H+
Cu2+
O2
CYP4A11
O2
NADPH
NADP+
CYP2A13
e-
H+
CYP4F2
NADPH
CYP3A7
Cl-
CYP2W1
18OH-ARA
CYP2C19
CYP2C8
NADP+
CYP2C19
NADPH
H2O
CYP450 (red.)
4CHOL7a,24(S)DONE
CYP2A7
CYP2A6
CYP19A1
5,6-EET
CYP4F11
CYP4F3
ALDH2
CYP4F22
DDCX
H2O
CHOL7a,24(S)DIOL
H2O
NADPH
H2O
Paraxanthine
NADP+
FAD
H+
NAD+
H2O2
CYP2D6
POMC(138-176)
H2O
NADPH
4CHOL7aOLONE
NADPH
CH2O
NADP+
19OH-PGH2
NADPH
CYP2A13
4-ethoxyaniline
CYP4F11
O2
H+
6BHT
O2
H+
HALO
ACV
CYP2F1
HOMZ
ARA
NADP+
PPi
CYP2E1
CYP2W1
O2
CYP2C19
O2
H2O
DSQ
H2O
NADPH
H+
CYP2C19
H2O
H2O
FDXR
CYP2F1
NADPH
NADP+
CYP4B1
H2O
CYP2F1
O2
NADP+
CYP4A11
NADPH
H+
6BHT
NADPH
ACSS2
NADP+
TES
H+
TYR
(2Fe-2S)(1+)
H+
EST17b
Zn2+
CTL
NADPH
NCOA1
TBXAS1
CES1
CDL
NADP+
CYP11B1
CYP3A43
H2O
NADP+
NADPH
NADPH
DHA
LPAM
H2O
CYP3A4
NADPH
CYP26C1
CYP4B1
NADP+
24OH-CHOL
AADAC
H2O
AOC2
Q6ZWL3
Uniprot
ALDO
P16435
Uniprot
CHEBI:4057
ChEBI
CHEBI:4058
ChEBI
H+
NADH
224930
Purification and partial characterization of aldehyde dehydrogenase from human erythrocytes.
Inoue K, Nishimukai H, Yamasawa K.
PubMed
CHEBI:31932
ChEBI
Zn2+
BPHL
NH3
HPHAC
H2O
NADH
CHEBI:46640
ChEBI
CYP2C19
CYP2D6
CHEBI:72790
ChEBI
CHEBI:36005
ChEBI
Q96DG6
Uniprot
CHEBI:48416
ChEBI
CYP2C18
P22760
Uniprot
O2
NADPH
O2
NADP+
CYP2S1
CYP2C19
4CHOL7a,12a,27TONE
H2O
TrXA3
LTB4
COUM
CHEBI:35854
ChEBI
CHEBI:2453
ChEBI
19HETE
18HCORST
Q86WA6
Uniprot
CXPA
11DCORST
CHEBI:16414
ChEBI
Q16853
Uniprot
CHEBI:17169
ChEBI
H+
O2
CYP26A1
NADP+
NADP+
CYP2D6
ADH1B
NADP+
CHEBI:8050
ChEBI
H+
P30837
Uniprot
H2O2
NADP+
NADPH
CHEBI:85505
ChEBI
CYP2A7
atRA
CHEBI:40574
ChEBI
CHEBI:17650
ChEBI
CHEBI:1294
ChEBI
CHEBI:34310
ChEBI
CHEBI:16581
ChEBI
NADPH
5HT
H2O
3AAPNAL
CHEBI:17813
ChEBI
4HPCP
O2
CYP4F22
CYP3A4
H2O
H2O
14,15-EET
CHEBI:17026
ChEBI
CYP2E1
TMA
NADPH
CHEBI:28694
ChEBI
Q16850
Uniprot
3MEIN
CHEBI:16469
ChEBI
CHEBI:40538
ChEBI
CHEBI:62845
ChEBI
O2
O75106
Uniprot
CHEBI:17500
ChEBI
NADP+
H+
NADPH
CYP2C9
CYP3A5
CHEBI:16113
ChEBI
CYP2S1
H+
CYP2B6
NADPH
CYP11A1
CYP2C8
ADH1C
CHEBI:17263
ChEBI
CHEBI:16474
ChEBI
O2
CHEBI:15378
ChEBI
CHEBI:18009
ChEBI
HCPM
NADP+
CYP4F2
NADPH
H+
Cu2+
O2
NADPH
CHEBI:15552
ChEBI
CDCA
O2
CYP4F11
CHEBI:15377
ChEBI
CYP2S1
CHEBI:16521
ChEBI
P05093
Uniprot
CYP2A13
CHEBI:42977
ChEBI
CYP4A11
H2O
H2O
CHEBI:37623
ChEBI
H+
H2O
P05091
Uniprot
CHEBI:15351
ChEBI
DEXM
CHEBI:15346
ChEBI
H2O
CHEBI:16908
ChEBI
CHEBI:30805
ChEBI
CHEBI:34157
ChEBI
H2O
CYP2C9
CHEBI:34130
ChEBI
NADPH
HCOOH
CHEBI:34490
ChEBI
NADPH
CHEBI:34450
ChEBI
4OH-EST17b
H2O
CHEBI:16973
ChEBI
Mg2+
CYP4B1
P00352
Uniprot
FAD
HPTXL
H2O
CHEBI:16236
ChEBI
H2O
CHEBI:29888
ChEBI
H2O
H+
NADH
P07327
Uniprot
CYP2F1
CYP2E1
Q9NR19
Uniprot
PTGS1
CYP2S1
CHEBI:15366
ChEBI
CYP3A43
P00326
Uniprot
H2O
P00325
Uniprot
H2O
AOC1
P28332
Uniprot
P08319
Uniprot
NADPH
CHEBI:15554
ChEBI
CHEBI:10545
ChEBI
NADP+
CHEBI:29105
ChEBI
P24557
Uniprot
NADP+
NADP+
H2O
H+
CYP1B1
CYP24A1
AOC3
CYP11A1
O2
I4AH
CYP2C9
PhOH
O2
EPHX1
CHEBI:15647
ChEBI
H2O
CYP2C8
CHEBI:4470
ChEBI
CYP4F2
NADPH
CHEBI:29133
ChEBI
H+
P40394
Uniprot
H2O
Q9NUB1
Uniprot
INDOL
MeOH
CYP7B1
4065146
Mitochondrial aldehyde dehydrogenase from human liver. Primary structure, differences in relation to the cytosolic enzyme, and functional correlations.
Hempel J, Kaiser R, Jörnvall H.
PubMed
TFAC
4OH-atRA
O2
H+
P4
O2
CH3CHO
O75881
Uniprot
CHEBI:26355
ChEBI
CYP4F3
CYP2A7
P23219
Uniprot
P01189
Uniprot
CHEBI:15646
ChEBI
H+
NADP+
CHOL3b,7a,25TRIOL
NADPH
CYP4F2
O2
CYP2C18
CHEBI:27510
ChEBI
MAOB
NADP+
CORST
CHEBI:63905
ChEBI
H2O
CHEBI:8107
ChEBI
CHEBI:63840
ChEBI
NADP+
CYP2J2
CHEBI:6532
ChEBI
P22680
Uniprot
H2O
MTZ
CYP51A1
P20813
Uniprot
NADP+
FAD
P05181
Uniprot
FAD
P10632
Uniprot
CYP4A22
Losec
CYP4F3
P33261
Uniprot
FDX1
CYP2C19
CHEBI:16842
ChEBI
H+
H+
H2O
H+
CHEBI:45863
ChEBI
H2O
CHEBI:63804
ChEBI
ISCAL
CoA-SH
CHEBI:30725
ChEBI
7
alpha-hydroxycholesterol
Hist
CHEBI:25858
ChEBI
EtOH
NADP+
O2
P11712
Uniprot
CYP2A13
P10635
Uniprot
18196
Two aldehyde dehydrogenases from human liver. Isolation via affinity chromatography and characterization of the isozymes.
Greenfield NJ, Pietruszko R.
PubMed
Q96SQ9
Uniprot
CHOL
P24903
Uniprot
P11509
Uniprot
H+
ADH6
Ac-CoA
CYP2F1
C2H4
H+
CHEBI:5615
ChEBI
P05177
Uniprot
NADPH
CHEBI:1784
ChEBI
CHEBI:27732
ChEBI
P33260
Uniprot
CHEBI:16580
ChEBI
Q9HB55
Uniprot
NADP+
O2
CYP2U1
NADP+
P20853
Uniprot
Q16696
Uniprot
NADP+
OM
Q7Z449
Uniprot
H+
3,16DOH-PALM
CHEBI:27385
ChEBI
CHEBI:17996
ChEBI
CHEBI:46195
ChEBI
CHEBI:29138
ChEBI
P13584
Uniprot
Q02928
Uniprot
CHEBI:29129
ChEBI
H2O
P51589
Uniprot
O2
Q8TAV3
Uniprot
NADP+
9cRA
Q5TCH4
Uniprot
PGH2
H2O
FMO2
P78329
Uniprot
O2
CHEBI:19138
ChEBI
CHEBI:39567
ChEBI
CHEBI:63799
ChEBI
ADH5
H2O
CHEBI:63590
ChEBI
CHEBI:17347
ChEBI
CYP2E1
Q9Y6A2
Uniprot
H2O
CYP2S1
CHEBI:17998
ChEBI
O2
HPHT
CHEBI:17703
ChEBI
Phenytoin
Q08477
Uniprot
CHEBI:28477
ChEBI
NADP+
Q6NT55
Uniprot
CHEBI:63839
ChEBI
P15538
Uniprot
Q9HBI6
Uniprot
ALDH1B1
NADP+
CHEBI:64043
ChEBI
H2O
CHEBI:34477
ChEBI
O2
CHEBI:1864
ChEBI
P04798
Uniprot
CHEBI:27999
ChEBI
NH3
CHEBI:17899
ChEBI
Acetaminophen (TN
TYLENOL)
CHEBI:48333
ChEBI
FDX1L
CHEBI:63838
ChEBI
CYP7A1
CYP2D6
CHEBI:15843
ChEBI
CYP4F8
CHEBI:48825
ChEBI
TAMO
H2O2
CYP26C1
CHEBI:4026
ChEBI
CHEBI:63859
ChEBI
CYP2A7
CHEBI:63800
ChEBI
O2
SPM
CYP2A13
CYP2C8
NADPH
CHEBI:18153
ChEBI
CHEBI:34665
ChEBI
PREG
CYP2C8
NADPH
CHOL
CYP2B6
CHEBI:37640
ChEBI
BaP4,5-DHD
20OH-LTB4
CHEBI:28750
ChEBI
H2O
ADH1A
Q02318
Uniprot
CHEBI:30751
ChEBI
Q16678
Uniprot
CHEBI:9171
ChEBI
CYP3A5
CHEBI:27561
ChEBI
CYP3A7
AMP
CYP3A7
CHEBI:28794
ChEBI
CYP2B6
H+
CYP4A22
CYP2C18
CYP2C9
CHEBI:7772
ChEBI
CHEBI:2504
ChEBI
11DCORT
CYP2B6
CHEBI:16422
ChEBI
P11511
Uniprot
NADP+
H+
NADPH
TYR
CYP2C9
O2
P08686
Uniprot
NADP+
CMBL
CHEBI:28324
ChEBI
ACSS1
Q9NYL5
Uniprot
PTXL
CYP2B6
NADPH
O2
H+
CCl4
BEG
2CEO
Ca2+
NADPH
BZAL
CYP21A2
H2O
H2O
Homo sapiens
Pathway is converted from Reactome id: (Reactome Converter)
Phase 1 of metabolism is concerned with <i><b>functionalization</b></i>, that is the introduction or exposure of functional groups on the chemical structure of a compound. This provides a 'handle' for phase 2 conjugating species with which to react with. Many xenobiotics are lipophilic and almost chemically inert (e.g. PAHs) so would not necessarily undergo a phase 2 reaction. Making them more chemically reactive would facilitate their excretion but also increases their chance of reacting with cellular macromolecules (e.g. proteins, DNA). There is a fine balance between producing a more reactive metabolite and conjugation reactions.<br>There are two groups of enzymes in phase 1 - oxidoreductases and hydrolases. Oxidoreductases introduce an oxygen atom into or remove electrons from their substrates. The major oxidoreductase enzyme system is called the P450 monooxygenases. Other systems include flavin-containing monooxygenases (FMO), cyclooxygenases (COX) and monoamine oxidases (MAO). Hydrolases hydrolyse esters, amides, epoxides and glucuronides.
View original pathway at:[http://www.reactome.org/PathwayBrowser/#DIAGRAM=211945 Reactome]. (WikiPathways-description)
Phase 1 - Functionalization of compounds
CYP2E1
CHEBI:63912
ChEBI
24OH-CHOL
CHEBI:15379
ChEBI
CHEBI:15627
ChEBI
H+
NASPN
CYP2J2
CYP2S1
CYP2A6
NADPH
H2O
O2
PAOX
H+
O2
H+
O2
RXRA
NADPH
CYP3A43
H2O2
H2O
NADPH
Oxindole
H2O2
CHEBI:16716
ChEBI
CYP17A1
CHEBI:28509
ChEBI
NADPH
CHEBI:47266
ChEBI
R-NUL-76433
Reactome
CHEBI:18276
ChEBI
CORT
SPN
CYP2J2
CYP2C8
LNSOL
CHEBI:81621
ChEBI
CYP2D6
O2
4CHOL7a,12a,24(S)TONE
CYP2J2
FAD
P23141
Uniprot
H+
CHEBI:41001
ChEBI
NAD+
CHEBI:34560
ChEBI
O00748
Uniprot
H+
POR
L-Val
H2O
CYP2A13
O2
NADPH
O2
H+
CHEBI:27958
ChEBI
CYP2F1
TMAO
CHEBI:17790
ChEBI
ALDH3A1
20OH-TrXA3
NADP+
CHEBI:196991
ChEBI
CHEBI:3410
ChEBI
P30838
Uniprot
H+
H2
TBM
MTZ-SOX
CTLA
AFB1
BaP4,5O
NADPH
NADP+
H+
NADP+
H+
H2O
CYP2A7
HCOOH
H2O
H+
CHEBI:29108
ChEBI
CHEBI:27398
ChEBI
P19801
Uniprot
P07099
Uniprot
CHEBI:18295
ChEBI
CYP2E1
ADH4
NADPH
CYP2S1
CYP3A43
CYP4F11
CoA-SH
CYP2C9
FAD
NADPH
PTCN
VC
P05108
Uniprot
FDXR
P22570
Uniprot
P10109
Uniprot
CYP2C8
H2O
H+
CHEBI:33738
ChEBI
H2O
Q6P4F2
Uniprot
10843999
Molecular characterization of human acetyl-CoA synthetase, an enzyme regulated by sterol regulatory element-binding proteins.
Luong A, Hannah VC, Brown MS, Goldstein JL.
PubMed
NHABP
PTGIS
CYP4F11
H+
CYP11B2
O43174
Uniprot
CYP2J2
Q6V0L0
Uniprot
CYP11B2
Q9NR63
Uniprot
CHEBI:63802
ChEBI
CHEBI:50648
ChEBI
CAF
O2
NH3
H+
NADP+
CH3COOH
CHEBI:83782
ChEBI
CYP450 (ox.)
CHEBI:48926
ChEBI
H+
CHEBI:15630
ChEBI
PTGIS
CHEBI:16225
ChEBI
H+
P11766
Uniprot
PGG2
O2
CYP2D6
HDoHE
H+
CYP4F2
CYP2D6
H2O
CYP2C19
CHEBI:16827
ChEBI
CHEBI:33737
ChEBI
CYP4F22
H2O
3AAPNAL
NADP+
O2
Q9NWM0-3
Uniprot
H+
CHEBI:27584
ChEBI
NADH
CHEBI:16485
ChEBI
CYP3A4
H2O
H2O2
H2O
HBr
NR1H4
H2O
P19099
Uniprot
P20815
Uniprot
CYP4A22
Phenylacetaldehyde
NASPM
P08684
Uniprot
CPM
P24462
Uniprot
ATP
O2
CYP2A13
CYP4F22
O2
CYP4F22
CYP2A7
Trichloromethyl
radical
11DCORST
CYP2A7
CYP2C9
O2
O2
HDBQ
H2O
acetyl group
CHEBI:16755
ChEBI
H+
Q15788
Uniprot
Q15596
Uniprot
Q96RI1
Uniprot
CYP4F12
CYP4F8
H2O
P19793
Uniprot
CHEBI:16325
ChEBI
NADP+
H+
H+
NADPH
H2O
11,12-EET
H2O
O2
O2
CYP7A1
ARA
NADPH
CYP2A6
NADPH
17aHPREG
VD3
NCOA2
P98187
Uniprot
ARA
CHEBI:28834
ChEBI
Q9UNU6
Uniprot
AFXBO
Q16647
Uniprot
Q9HCS2
Uniprot
H2O
NADP+
TES
4CHOL7a,27DONE
O2
CYP2C8
4HPAA
NADP+
TXA2
CH3COO-
LCHA
NADPH
H2O
H+
20OH-LTB4
CYP2R1
NADPH
HCOU
NADPH
NADP+
heme b
NADP+
Ca2+
4CHOL7a,12aDONE
CYP2C9
NADP+
NADPH
H2O
S-FGSH
NH3
EtOH
CYP2B6
CYP4F12
CYP2F1
NADP+
(2Fe-2S)2+
NADPH
O2
O2
CYP2C8
CYP27A1
O2
CYP1A1
CYP39A1
O2
H+
H+
H2O
NADPH
PEA
O2
O2
E1
O2
H2O
CYP1A2
H2O
CHEBI:17823
ChEBI
CYP2F1
BZAM
O2
O15528
Uniprot
CHEBI:15367
ChEBI
H2O
CHEBI:63911
ChEBI
Q07973
Uniprot
NADP+
H2O
NADP+
H2O
MIND
H+
4,4DMCHtOL
FMO1
CYP2C19
CYP2A6
CHEBI:63998
ChEBI
CYP2A7
CHEBI:63795
ChEBI
CYP3A5
CYP8B1
H+
S-HMGSH
CHEBI:37248
ChEBI
H2O
27OH-CHOL
CHEBI:31697
ChEBI
NADP+
CHEBI:16881
ChEBI
C6H6
CYP2S1
N-demethylated
loperamide
H+
3APAL
NAD+
LTB4
CYP4A22
ALDH1A1
O2
CYP2A7
NABQI
EtO
20a,22b-DHCHOL
CYP4A22
ATP
O2
CYP2E1
H2O
NADPH
CYP26B1
H+
CHEBI:15882
ChEBI
NH3
H2O
CHEBI:28940
ChEBI
CHEBI:29132
ChEBI
NADPH
CYP2A13
H+
Q6VVX0
Uniprot
CHEBI:17933
ChEBI
H2O
NADP+
NADPH
HTOLB
FMO3
H+
CH3CHO
H+
NADPH
CYP2F1
NADPH
CYP4F3
CYP4F8
H+
NADP+
P27338
Uniprot
H2O
P21397
Uniprot
FDX1
CHEBI:27647
ChEBI
Q01740
Uniprot
CHEBI:18420
ChEBI
CYP2B6
ANDST
NADP+
H+
NADP+
O2
CYP46A1
COCN
8,9-EET
CHEBI:28790
ChEBI
NADP+
NADP+
CYP2C9
CHEBI:15760
ChEBI
PGI2
CHEBI:15621
ChEBI
CHEBI:16134
ChEBI
Ac-CoA
The start coordinate is not yet known (Reactome)
CYP27B1(?-508)
CHEBI:16240
ChEBI
H2O2
CYP2E1
SPM
CHEBI:63825
ChEBI
CHEBI:15724
ChEBI
25OH-CHOL
O2
CHEBI:18139
ChEBI
CYP2C18
NAD+
CHEBI:50673
ChEBI
DCA
CHEBI:63904
ChEBI
H+
CYP7B1
O2
CES2
CYP4B1
NADPH
NADP+
12-HETE
CHEBI:63828
ChEBI
Q99518
Uniprot
5HIALD
MAOA
CHEBI:41774
ChEBI
P31513
Uniprot
CHEBI:16238
ChEBI
CYP2B6
Q6QHF9
Uniprot
NADPH
CHEBI:15422
ChEBI
CYP4F2
CHEBI:15846
ChEBI
OLMS
CHEBI:16027
ChEBI
CYP8B1
CHEBI:15343
ChEBI
O2
CYP4F22
O2
CYP2A13
NADPH
CTL
FDX1L
NH3
O2
PPi
NADP+
VACV
PHEN
AMP
CHEBI:18397
ChEBI
DEXT
CHEBI:50157
ChEBI
H+
CHEBI:17927
ChEBI
O2
PGH2
CHEBI:16424
ChEBI
O2
3OH-PALM
NADP+
CHEBI:17312
ChEBI
diketone
CH2O
NADPH
O2
CYP4F2
O2
CHEBI:30322
ChEBI
CHEBI:15746
ChEBI
CHEBI:18090
ChEBI
CHEBI:17148
ChEBI
CHEBI:16610
ChEBI
CYP4A11
H2O2