Entry
Name
aromatase;
CYP19A1 (gene name);
estrogen synthetase (incorrect)
Class
Oxidoreductases;
Acting on paired donors, with incorporation or reduction of molecular oxygen;
With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
BRITE hierarchy
Sysname
testosteronel,NADPH---hemoprotein reductase:oxygen oxidoreductase (17beta-estradiol-forming)
Reaction(IUBMB)
(1) testosterone + 3 O2 + 3 [reduced NADPH---hemoprotein reductase] = 17beta-estradiol + formate + 4 H2O + 3 [oxidized NADPH---hemoprotein reductase] (overall reaction) [RN:
R10511 ];
(1a) testosterone + O2 + [reduced NADPH---hemoprotein reductase] = 19-hydroxytestosterone + H2O + [oxidized NADPH---hemoprotein reductase] [RN:
R02501 ];
(1b) 19-hydroxytestosterone + O2 + [reduced NADPH---hemoprotein reductase] = 19-oxotestosterone + 2 H2O + [oxidized NADPH---hemoprotein reductase] [RN:
R04761 ];
(1c) 19-oxotestosterone + O2 + [reduced NADPH---hemoprotein reductase] = 17beta-estradiol + formate + H2O + [oxidized NADPH---hemoprotein reductase] [RN:
R03087 ];
(2) androst-4-ene-3,17-dione + 3 O2 + 3 [reduced NADPH---hemoprotein reductase] = estrone + formate + 4 H2O + 3 [oxidized NADPH---hemoprotein reductase] (overall reaction) [RN:
R10515 ];
(2a) androst-4-ene-3,17-dione + O2 + [reduced NADPH---hemoprotein reductase] = 19-hydroxyandrost-4-ene-3,17-dione + H2O + [oxidized NADPH---hemoprotein reductase] [RN:
R01840 ];
(2b) 19-hydroxyandrost-4-ene-3,17-dione + O2 + [reduced NADPH---hemoprotein reductase] = 19-oxo-androst-4-ene-3,17-dione + 2 H2O + [oxidized NADPH---hemoprotein reductase] [RN:
R04759 ];
(2c) 19-oxoandrost-4-ene-3,17-dione + O2 + [reduced NADPH---hemoprotein reductase] = estrone + formate + H2O + [oxidized NADPH---hemoprotein reductase] [RN:
R02351 ]
Reaction(KEGG)
Substrate
testosterone [CPD:
C00535 ];
O2 [CPD:
C00007 ];
[reduced NADPH---hemoprotein reductase] [CPD:
C03024 ];
19-hydroxytestosterone [CPD:
C05294 ];
19-oxotestosterone [CPD:
C05295 ];
androst-4-ene-3,17-dione [CPD:
C00280 ];
19-hydroxyandrost-4-ene-3,17-dione [CPD:
C05290 ];
19-oxoandrost-4-ene-3,17-dione [CPD:
C05297 ]
Product
17beta-estradiol;
formate [CPD:
C00058 ];
H2O [CPD:
C00001 ];
[oxidized NADPH---hemoprotein reductase] [CPD:
C03161 ];
19-hydroxytestosterone [CPD:
C05294 ];
19-oxotestosterone [CPD:
C05295 ];
estrone [CPD:
C00468 ];
19-hydroxyandrost-4-ene-3,17-dione [CPD:
C05290 ];
19-oxo-androst-4-ene-3,17-dione
Comment
A cytochrome P-450. The enzyme catalyses three sequential hydroxylations of the androgens androst-4-ene-3,17-dione and testosterone, resulting in their aromatization and forming the estrogens estrone and 17beta-estradiol, respectively. The direct electron donor to the enzyme is EC
1.6.2.4 , NADPH---hemoprotein reductase.
History
EC 1.14.14.14 created 2013
Pathway
ec00140 Steroid hormone biosynthesis
Orthology
Genes
PANU : 100997810 116272542
CCAN : 109675669 109679172
CHX : 100861413(CYP19A1) 102172726
BTAX : 128054322 128054328
SSC : 403331(CYP19A1) 403332(CYP19A2) 403333(CYP19A3)
CDK : 105086637 105106135 116153434
BACU : 103011787 103012080
DLE : 111170860 111170861 111171015
PCAD : 102982383 102982657 102995165
PSIU : 116749060 116749147
NASI : 112397422 112397499
BBUF : 120985817 120985818
BGAR : 122927630 122927631
DRE : 30390(cyp19a1a) 60640(cyp19a1b)
SANH : 107674832 107700584
CCAR : 109051432 109068452 109072133
CAUA : 113042873 113061867 113082814 113118576
CGIB : 127934323 127977536 128014519
PTET : 122330655 122362496
LROH : 127156350 127181253
PPRM : 120477771 120485850
MAMB : 125246945 125254507
CIDE : 127500194 127507121
MASI : 127436251 127456148
TROS : 130549838 130551793
MANU : 129419642 129433099
PHYP : 113530142 113534440
SMEO : 124392156 124395700
AMEX : 103033668 103038449
CMAO : 118804009 118811907
CHAR : 105889015 105892489
TRU : 100379639(pfcyp19b-tstr) 101076508(pfcyp19a)
TNG : GSTEN00018058G001 GSTEN00025591G001
CGOB : 115009664 115024369
PLEP : 121947240 121949866
SLUC : 116038508 116054646
ECRA : 117939964 117949645
PFLV : 114557236 114559505
PPUG : 119196278 119197603
CLUM : 117732474 117750439
MSAM : 119890709 119893898
SCHU : 122875290 122875399
ALAT : 119017644 119023827
MZE : 101468629 106675461 112431276
OLA : 100125815(cyp19b) 101174651
PRET : 103462065 103466459
PFOR : 103143597 103156494
PLAI : 106947725 106960953
PMEI : 106912224 106932411
CTUL : 119782422 119792512
ALIM : 106521145 106530933 106536387
AOCE : 111565746 111577263
MCEP : 125005804 125014725
CSEM : 103378914 103380488
SSEN : 122772648 122776510
HHIP : 117754230 117762605 117778658
HSP : 118103743 118109472 118122615 124851147
SLAL : 111656853 111666923
SSCV : 125967127 125970121
BPEC : 110169315 110172912
MALB : 109963333 109974150
BSPL : 114852301 114857594
SASA : 106562534 106584746(CYP19B) 106587170(CYP19)
STRU : 115166948 115192897 115203363
OMY : 110506809 110506810 110521201
SALP : 112068480 112073830
SNH : 120048793 120048801 120052328
CCLU : 121540733 121579689
PSPA : 121294903 121299384
ARUT : 117428169 117429562
BBEL : 109471188 109481437
» show all
Taxonomy
Reference
Authors
Thompson EA Jr, Siiteri PK
Title
The involvement of human placental microsomal cytochrome P-450 in aromatization.
Journal
J Biol Chem 249:5373-8 (1974)
Reference
Authors
Fishman J, Goto J
Title
Mechanism of estrogen biosynthesis. Participation of multiple enzyme sites in placental aromatase hydroxylations.
Journal
J Biol Chem 256:4466-71 (1981)
Reference
Authors
Kellis JT Jr, Vickery LE
Title
Purification and characterization of human placental aromatase cytochrome P-450.
Journal
J Biol Chem 262:4413-20 (1987)
Reference
Authors
Ghosh D, Griswold J, Erman M, Pangborn W
Title
Structural basis for androgen specificity and oestrogen synthesis in human aromatase.
Journal
Sequence
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