1.14.15.6: cholesterol monooxygenase (side-chain-cleaving)
This is an abbreviated version!
For detailed information about cholesterol monooxygenase (side-chain-cleaving), go to the full flat file.
Word Map on EC 1.14.15.6
-
1.14.15.6
-
steroidogenic
-
steroidogenesis
-
star
-
progesterone
-
testosterone
-
ovarian
-
pregnenolone
-
granulosa
-
leydig
-
ovary
-
follicle
-
androgen
-
testis
-
testicular
-
lh
-
lutein
-
aromatase
-
adrenodoxin
-
gonad
-
cyp17a1
-
adrenocortical
-
estradiol
-
acth
-
cortisol
-
gonadotropin
-
follicular
-
3beta-hydroxysteroid
-
hsd3b1
-
3beta-hsd
-
theca
-
androstenedione
-
p450arom
-
aminoglutethimide
-
cyp11b2
-
neurosteroids
-
22r-hydroxycholesterol
-
21-hydroxylase
-
lhcgr
-
hsd17b3
-
scarb1
-
synthesis
-
medicine
-
cyp21
-
hcg-stimulated
-
biotechnology
-
lipoid
-
fsh-induced
-
11beta-hydroxylase
-
srd5a1
-
interrenal
-
analysis
-
17alpha-hydroxylase
-
drug development
-
trilostane
-
fsh-stimulated
- 1.14.15.6
-
steroidogenic
-
steroidogenesis
- star
- progesterone
- testosterone
- ovarian
- pregnenolone
-
granulosa
- leydig
- ovary
- follicle
- androgen
- testis
- testicular
- lh
- lutein
- aromatase
- adrenodoxin
- gonad
- cyp17a1
-
adrenocortical
- estradiol
- acth
- cortisol
- gonadotropin
- follicular
-
3beta-hydroxysteroid
- hsd3b1
- 3beta-hsd
-
theca
- androstenedione
- p450arom
- aminoglutethimide
- cyp11b2
-
neurosteroids
-
22r-hydroxycholesterol
- 21-hydroxylase
-
lhcgr
- hsd17b3
-
scarb1
- synthesis
- medicine
- cyp21
-
hcg-stimulated
- biotechnology
-
lipoid
-
fsh-induced
-
11beta-hydroxylase
- srd5a1
-
interrenal
- analysis
- 17alpha-hydroxylase
- drug development
- trilostane
-
fsh-stimulated
Reaction
Synonyms
C27-side chain cleavage enzyme, cholesterol 20-22-desmolase, cholesterol C20-22 desmolase, cholesterol C20-C22 lyase, cholesterol desmolase, cholesterol hydroxylase, cholesterol side chain cleavage cytochrome P450, cholesterol side chain cleavage enzyme, cholesterol side-chain cleavage cytochrome P450, cholesterol side-chain cleavage cytochrome P450 enzyme, cholesterol side-chain cleavage enzyme, cholesterol side-chain-cleaving enzyme, cholesterol side-cleaving enzyme, CYP 11A1, Cyp11a, CYP11A1, CYPXIA1, cytochrome P-450scc, cytochrome P450 11A1, cytochrome P450 cholesterol side chain cleavage, cytochrome P450 cholesterol side-chain cleavage, cytochrome P450 side chain cleavage enzyme, cytochrome P450-mediated cholesterol side-chain cleavage enzyme, cytochrome P450-mediated side-chain cleavage enzyme, cytochrome P450scc, desmolase, steroid 20-22, endoenzymes, cholesterol side-chain-cleaving, enzymes, cholesterol side-chain-cleaving, P450 11A1, P450 cholesterol side chain cleaving enzyme, P450 cholesterol side-chain cleavage enzyme, P450(scc), P450scc, steroid 20-22 desmolase, steroid 20-22-lyase
ECTree
1.14.15.6 cholesterol monooxygenase (side-chain-cleaving)Advanced search results
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Reference on EC 1.14.15.6 - cholesterol monooxygenase (side-chain-cleaving)
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REF. 
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Hanukoglu, I.; Jefcoate, C.R.
Mitochondrial cytochrome P-450sec. Mechanism of electron transport by adrenodoxin
J. Biol. Chem.
255
3057-3061
1980
Bos taurus
Hanukoglu, I.; Spitsberg, V.; Bumpus, J.A.; Dus, K.M.; Jefcoate, C.R.
Adrenal mitochondrial cytochrome P-450scc. Cholesterol and adrenodoxin interactions at equilibrium and during turnover
J. Biol. Chem.
256
4321-4328
1981
Bos taurus
Hanukoglu, I.; Privalle, C.T.; Jefcoate, C.R.
Mechanisms of ionic activation of adrenal mitochondrial cytochromes P-450scc and P-45011beta
J. Biol. Chem.
256
4329-4335
1981
Bos taurus
Wang, H.P.; Kimura, T.
Purification and characterization of adrenal cortex mitochondrial cytochrome P-450 specific for cholesterol side chain cleavage activity
J. Biol. Chem.
251
6068-6074
1976
Bos taurus
Nakajin, S.; Ishii, Y.; Shinoda, M.
Binding of Triton X-100 to purified cytochrome P-450scc and enhancement of the cholesterol side chain cleavage activity
Biochem. Biophys. Res. Commun.
87
524-531
1979
Bos taurus
Hume, R.; Kelly, R.W.; Taylor, P.L.; Boyd, G.S.
The catalytic cycle of cytochrome P-450scc and intermediates in the conversion of cholesterol to pregnenolone
Eur. J. Biochem.
140
583-591
1984
Bos taurus
Shikita, M.; Hall, P.F.
Cytochrome P-450 from bovine adrenocortical mitochondria: an enzyme for the side chain cleavage of cholesterol. I. Purification and properties
J. Biol. Chem.
248
5598-5604
1973
Bos taurus
Takemori, S.; Sukara, K.; Hashimoto, K.; Hashimoto, M.; Sato, H.; Gomi, T.; Katagiri, M.
Purification of cytochrome P-450 from bovine adrenocortical mitochondria by an aniline-Sepharose and the properties
Biochem. Biophys. Res. Commun.
63
588-593
1975
Bos taurus
Dhariwal, M.S.; Jefcoate, C.R.
Cholesterol metabolism by purified cytochrome P-450scc is highly stimulated by octyl glucoside and stearic acid exclusively in large unilamellar phospholipid vesicles
Biochemistry
28
8397-8402
1989
Bos taurus
Lambeth, J.D.; Kriengsiri, S.
Cytochrome P-450scc-adrenodoxin interactions. Ionic effects on binding, and regulation of cytochrome reduction by bound steroid substrates
J. Biol. Chem.
260
8810-8816
1985
Bos taurus
Nagahisa, A.; Foo, T.; Gut, M.; Orme-Johnson, W.H.
Competitive inhibition of cytochrome P-450scc by (22R)- and (22S)-22-aminocholesterol. Side-chain stereochemical requirements for C-22 amine coordination to the active-site heme
J. Biol. Chem.
260
846-851
1985
Bos taurus
Kashiwagi, K.; Dafeldecker, W.P.; Salhanick, H.A.
Purification and characterization of mitochondrial cytochrome P-450 associated with cholesterol side chain cleavage from bovine corpus luteum
J. Biol. Chem.
255
2606-2611
1980
Bos taurus
Sheets, J.J.; Vickery, L.E.
Active site-directed inhibitors of cytochrome P-450scc. Structural and mechanistic implications of a side chain-substituted series of amino-steroids
J. Biol. Chem.
258
11446-11452
1983
Bos taurus
Sheets, J.J.; Vickery, L.E.
C-22-Substituted steroid derivatives as substrate analogues and inhibitors of cytochrome P-450scc
J. Biol. Chem.
258
1720-1725
1983
Bos taurus
Warne, P.A.; Greenfield, N.J.; Lieberman, S.
Modulation of the kinetics of cholesterol side-chain cleavage by an activator and by an inhibitor isolated from the cytosol of the cortex of bovine adrenals
Proc. Natl. Acad. Sci. USA
80
1877-1881
1983
Bos taurus
Shikita, M.; Hall, P.F.
Cytochrome P-450 from bovine adrenocortical mitochondria: an enzyme for the side chain cleavage of cholesterol. II. Subunit structure
J. Biol. Chem.
248
5605-5609
1973
Bos taurus
Miao, E.; Joardar, S.; Zuo, C.; Cloutier, N.J.; Nagahisa, A.; Byon, C.; Wilson, S.R.; Orme-Johnson, W.H.
Cytochrome P-450scc-mediated oxidation of (20S)-22-thiacholesterol: Characterization of mechanism-based inhibition
Biochemistry
34
8415-8421
1995
Bos taurus
Schwarz, D.; Kisselev, P.; Wessel, R.; Jueptner, O.; Schmid, R.D.
alpha-Branched 1,2-diacyl phosphatidylcholines as effectors of activity of cytochrome P450SCC (CYP11A1). Modeling the structure of the fatty acyl chain region of cardiolipin
J. Biol. Chem.
271
12840-12846
1996
Bos taurus
Lepesheva, G.I.; Azeva, T.N.; Strushkevich, N.V.; Gilep, A.A.; Usanov, S.A.
Site-directed mutagenesis of cytochrome P450scc (CYP11A1). Effect of lysine residue substitution on its structural and functional properties
Biochemistry (Moscow)
65
1409-1418
2000
Bos taurus
Ahmed, S.
The use of the novel substrate-heme complex approach in the derivation of a representation of the active site of the enzyme cholesterol side chain cleavage
Biochem. Biophys. Res. Commun.
274
821-824
2000
Bos taurus
Tsujita, M.; Ichikawa, Y.
Substrate-binding region of cytochrome P-450scc (P-450 XIA1). Identification and primary structure of the cholesterol binding region in cytochrome P-450scc
Biochim. Biophys. Acta
1161
124-130
1993
Bos taurus
Usanov, S.A.; Graham, S.E.; Lepesheva, G.I.; Azeva, T.N.; Strushkevich, N.V.; Gilep, A.A.; Estabrook, R.W.; Peterson, J.
Probing the interaction of bovine cytochrome P450scc (CYP11A1) with adrenodoxin: evaluating site-directed mutations by molecular modeling
Biochemistry
41
8310-8320
2002
Bos taurus
Headlam, M.J.; Tuckey, R.C.
The effect of glycerol on cytochrome P450scc (CYP11A1) spin state, activity, and hydration
Arch. Biochem. Biophys.
407
95-102
2002
Bos taurus
Abd-Elaziz, M.; Moriya, T.; Akahira, J.; Suzuki, T.; Sasano, H.
StAR and progesterone producing enzymes (3beta-hydroxysteroid dehydrogenase and cholesterol side-chain cleavage cytochromes P450) in human epithelial ovarian carcinoma: immunohistochemical and real-time PCR studies
Cancer Sci.
96
232-239
2005
Homo sapiens
Nazarov, P.A.; Drutsa, V.L.; Miller, W.L.; Shkumatov, V.M.; Luzikov, V.N.; Novikova, L.A.
Formation and functioning of fused cholesterol side-chain cleavage enzymes
DNA Cell Biol.
22
243-252
2003
Bos taurus, Homo sapiens
Vilchis, F.; Chavez, B.; Larrea, F.; Timossi, C.; Montiel, F.
The cDNA cloning and tissue expression of the cytochrome P450scc from Syrian hamster (Mesocricetus auratus)
Gen. Comp. Endocrinol.
126
279-286
2002
Mesocricetus auratus (Q9EPT4), Mesocricetus auratus
Patte-Mensah, C.; Kappes, V.; Freund-Mercier, M.J.; Tsutsui, K.; Mensah-Nyagan, A.G.
Cellular distribution and bioactivity of the key steroidogenic enzyme, cytochrome P450side chain cleavage, in sensory neural pathways
J. Neurochem.
86
1233-1246
2003
Rattus norvegicus
Tuckey, R.C.; Headlam, M.J.
Placental cytochrome P450scc (CYP11A1): comparison of catalytic properties between conditions of limiting and saturating adrenodoxin reductase
J. Steroid Biochem. Mol. Biol.
81
153-158
2002
Homo sapiens
Endo, H.; Okanoya, K.; Park, T.J.; Sasaki, M.; Tanemura, K.; Kimura, J.; Hayashi, Y.
Localization of the cytochrome P450 side-chain cleavage enzyme in the inactive testis of the naked mole-rat
Zool. Sci.
19
673-678
2002
Heterocephalus glaber
Pikuleva, I.A.
Cholesterol-metabolizing cytochromes P450
Drug Metab. Dispos.
34
513-520
2006
Homo sapiens
Arukwe, A.
Modulation of brain steroidogenesis by affecting transcriptional changes of steroidogenic acute regulatory (StAR) protein and cholesterol side chain cleavage (P450scc) in juvenile atlantic salmon (Salmo salar) is a novel aspect of nonylphenol toxicity
Environ. Sci. Technol.
39
9791-9798
2005
Salmo salar
Ijiri, S.; Takei, N.; Kazeto, Y.; Todo, T.; Adachi, S.; Yamauchi, K.
Changes in localization of cytochrome P450 cholesterol side-chain cleavage (P450scc) in Japanese eel testis and ovary during gonadal development
Gen. Comp. Endocrinol.
145
75-83
2006
Anguilla japonica (Q4KYY5), Anguilla japonica
Hsu, H.T.; Chang, Y.C.; Chiu, Y.N.; Liu, C.L.; Chang, K.J.; Guo, I.C.
Leptin interferes with adrenocorticotropin/3',5'-cyclic adenosine monophosphate (cAMP) signaling, possibly through a janus kinase 2-phosphatidylinositol 3-kinase/akt-phosphodiesterase 3-cAMP pathway, to down-regulate cholesterol side-chain cleavage cytochrome P450 enzyme in human adrenocortical NCI-H295 cell line
J. Clin. Endocrinol. Metab.
91
:2761-2769
2006
Homo sapiens
-
Kazeto, Y.; Ijiri, S.; Adachi, S.; Yamauchi, K.
Cloning and characterization of a cDNA encoding cholesterol side-chain cleavage cytochrome P450 (CYP11A1): tissue-distribution and changes in the transcript abundance in ovarian tissue of Japanese eel, Anguilla japonica, during artificially induced sexual development
J. Steroid Biochem. Mol. Biol.
99
121-128
2006
Anguilla japonica (Q4KYY5), Anguilla japonica
Rekawiecki, R.; Nomik, M.; Kotwica, J.
Stimulatory effect of LH, PGE2 and progesterone on StAR protein, cytochrome P450 cholesterol side chain cleavage and 3beta hydroxysteroid dehydrogenase gene expression in bovine luteal cells
Prostaglandins other Lipid Mediat.
78
169-184
2005
Bos taurus
Miura, S.; Nakamura, S.; Kobayashi, Y.; Piferrer, F.; Nakamura, M.
Differentiation of ambisexual gonads and immunohistochemical localization of P450 cholesterol side-chain cleavage enzyme during gonadal sex differentiation in the protandrous anemonefish, Amphiprion clarkii
Comp. Biochem. Physiol. B
149
29-37
2008
Amphiprion clarkii
Kim, C.J.; Lin, L.; Huang, N.; Quigley, C.A.; AvRuskin, T.W.; Achermann, J.C.; Miller, W.L.
Severe combined adrenal and gonadal deficiency caused by novel mutations in the cholesterol side chain cleavage enzyme, P450scc
J. Clin. Endocrinol. Metab.
93
696-702
2008
Homo sapiens (P05108), Homo sapiens
Martinez, A.A.; Munoz, Y.R.; Serrano, F.S.; Garcia, P.M.
Immunolocalization of cholesterol side chain cleavage enzyme (P450scc) in Mytilus galloprovincialis and its induction by nutritional levels
J. Comp. Physiol. B
178
647-654
2008
Mytilus galloprovincialis
Chiu, C.H.; Wei, H.W.; Wu, L.S.
Generation and utilization of P450 cholesterol side-chain cleavage enzyme and 3beta-hydroxysteroid dehydrogenase antibodies for universal detection
J. Immunoassay Immunochem.
29
152-160
2008
Bos taurus, Sus scrofa, Capra aegagrus
Minenko, A.N.; Novikova, L.A.; Luzikov, V.N.; Kovaleva, I.E.
Import of hybrid forms of CYP11A1 into yeast mitochondria
Biochim. Biophys. Acta
1780
1121-1130
2008
synthetic construct
Carrara, S.; Shumyantseva, V.V.; Archakov, A.I.; Samori, B.
Screen-printed electrodes based on carbon nanotubes and cytochrome P450scc for highly sensitive cholesterol biosensors
Biosens. Bioelectron.
24
148-150
2008
synthetic construct
Arukwe, A.
Steroidogenic acute regulatory (StAR) protein and cholesterol side-chain cleavage (P450scc)-regulated steroidogenesis as an organ-specific molecular and cellular target for endocrine disrupting chemicals in fish
Cell Biol. Toxicol.
24
527-540
2008
Gadus morhua, Oncorhynchus mykiss, Salmo salar
Nguyen, M.N.; Slominski, A.; Li, W.; Ng, Y.R.; Tuckey, R.C.
Metabolism of vitamin d2 to 17,20,24-trihydroxyvitamin d2 by cytochrome p450scc (CYP11A1)
Drug Metab. Dispos.
37
761-767
2009
Bos taurus
Tuckey, R.C.; Li, W.; Zjawiony, J.K.; Zmijewski, M.A.; Nguyen, M.N.; Sweatman, T.; Miller, D.; Slominski, A.
Pathways and products for the metabolism of vitamin D3 by cytochrome P450scc
FEBS J.
275
2585-2596
2008
Bos taurus
Spivak, S.; Berdichevets, I.; Iarmolinskiǐ, D.; Maneshina, T.; Shpakovskiǐ, G.; Kartel, N.
Construction and characteristics of transgenic tobacco Nicotiana tabacum L. plants expressing CYP11A1 cDNA encoding cytochrome P450scc
Genetika
45
1217-1224
2009
Bos taurus
Tuckey, R.C.; Nguyen, M.N.; Slominski, A.
Kinetics of vitamin D3 metabolism by cytochrome P450scc (CYP11A1) in phospholipid vesicles and cyclodextrin
Int. J. Biochem. Cell Biol.
40
2619-2626
2008
Bos taurus
Pikuleva, I.A.; Mast, N.; Liao, W.L.; Turko, I.V.
Studies of membrane topology of mitochondrial cholesterol hydroxylases CYPs 27A1 and 11A1
Lipids
43
1127-1132
2008
Bos taurus
Teplyuk, N.M.; Zhang, Y.; Lou, Y.; Hawse, J.R.; Hassan, M.Q.; Teplyuk, V.I.; Pratap, J.; Galindo, M.; Stein, J.L.; Stein, G.S.; Lian, J.B.; van Wijnen, A.J.
The osteogenic transcription factor runx2 controls genes involved in sterol/steroid metabolism, including CYP11A1 in osteoblasts
Mol. Endocrinol.
23
849-861
2009
Homo sapiens, Mus musculus
Irving-Rodgers, H.F.; Harland, M.L.; Sullivan, T.R.; Rodgers, R.J.
Studies of granulosa cell maturation in dominant and subordinate bovine follicles: novel extracellular matrix focimatrix is co-ordinately regulated with cholesterol side-chain cleavage CYP11A1
Reproduction
137
825-834
2009
Bos taurus
Rangel, P.L.; Rodriguez, A.; Rojas, S.; Sharp, P.J.; Gutierrez, C.G.
Testosterone stimulates progesterone production and STAR, P450 cholesterol side-chain cleavage and LH receptor mRNAs expression in hen (Gallus domesticus) granulosa cells
Reproduction
138
961-969
2009
Gallus gallus
Nakamoto, M.; Fukasawa, M.; Orii, S.; Shimamori, K.; Maeda, T.; Suzuki, A.; Matsuda, M.; Kobayashi, T.; Nagahama, Y.; Shibata, N.
Cloning and expression of medaka cholesterol side chain cleavage cytochrome P450 during gonadal development
Dev. Growth Differ.
52
385-395
2010
Oryzias latipes
Evans, A.; Nunez, B.
Regulation of mRNAs encoding the steroidogenic acute regulatory protein and cholesterol side-chain cleavage enzyme in the elasmobranch interrenal gland
Gen. Comp. Endocrinol.
168
121-132
2010
Hypanus sabinus (D0EFX3), Hypanus sabinus
Warita, K.; Mitsuhashi, T.; Sugawara, T.; Tabuchi, Y.; Tanida, T.; Wang, Z.; Matsumoto, Y.; Yokoyama, T.; Kitagawa, H.; Miki, T.; Takeuchi, Y.; Hoshi, N.
Direct effects of diethylstilbestrol on the gene expression of the cholesterol side-chain cleavage enzyme (P450scc) in testicular Leydig cells
Life Sci.
87
281-285
2010
Mus musculus
Slominski, A.T.; Janjetovic, Z.; Fuller, B.E.; Zmijewski, M.A.; Tuckey, R.C.; Nguyen, M.N.; Sweatman, T.; Li, W.; Zjawiony, J.; Miller, D.; Chen, T.C.; Lozanski, G.; Holick, M.F.
Products of vitamin D3 or 7-dehydrocholesterol metabolism by cytochrome P450scc show anti-leukemia effects, having low or absent calcemic activity
PLoS ONE
5
e9907
2010
Homo sapiens
Schiffler, B.; Zoellner, A.; Bernhardt, R.
Kinetic and optical biosensor study of adrenodoxin mutant AdxS112W displaying an enhanced interaction towards the cholesterol side chain cleavage enzyme (CYP11A1)
Eur. Biophys. J.
40
1275-1282
2011
Homo sapiens
Mast, N.; Annalora, A.; Lodowski, D.; Palczewski, K.; Stout, C.; Pikuleva, I.
Structural basis for three-step sequential catalysis by the cholesterol side chain cleavage enzyme CYP11A1
J. Biol. Chem.
286
5607-5613
2011
Bos taurus (P00189)
Pagotto, M.; Roldan, M.; Pagotto, R.; Lugano, M.; Pisani, G.; Rogic, G.; Molinas, S.; Trumper, L.; Pignataro, O.; Monasterolo, L.
Localization and functional activity of cytochrome P450 side chain cleavage enzyme (CYP11A1) in the adult rat kidney
Mol. Cell. Endocrinol.
332
253-260
2011
Rattus norvegicus, Rattus norvegicus Wistar
Wang, J.; Sun, J.; Qi, F.; Song, Q.; Niu, S.; Hui, C.; Xu, T.; He, F.
Effect of heshouwuyin on protein expression of steroidogenic acute regulatory protein and cytochrome P450 cholesterol side chain cleavage enzyme in Leydig cells of rats
Acta Anatomica Sinica
48
30-36
2017
Rattus norvegicus (P14137)
-
Davydov, R.; Strushkevich, N.; Smil, D.; Yantsevich, A.; Gilep, A.; Usanov, S.; Hoffman, B.M.
Evidence that compound I is the active species in both the hydroxylase and lyase steps by which P450scc converts cholesterol to pregnenolone EPR/ENDOR/cryoreduction/annealing Studies
Biochemistry
54
7089-7097
2015
Homo sapiens (P05108)
Kubeil, C.; Yeung, J.; Tuckey, R.; Rodgers, R.; Martin, L.
Membrane-mediated protein-protein interactions of cholesterol side-chain cleavage cytochrome P450 with its associated electron transport proteins
ChemPlusChem
81
995-1002
2016
Bos taurus (P00189)
-
Cook, J.B.; Werner, D.F.; Maldonado-Devincci, A.M.; Leonard, M.N.; Fisher, K.R.; OBuckley, T.K.; Porcu, P.; McCown, T.J.; Besheer, J.; Hodge, C.W.; Morrow, A.L.
Overexpression of the steroidogenic enzyme cytochrome P450 side chain cleavage in the ventral tegmental area increases 3alpha,5alpha-THP and reduces long-term operant ethanol self-administration
J. Neurosci.
34
5824-5834
2014
Rattus norvegicus (P14137)
Efimova, V.S.; Isaeva, L.V.; Makeeva, D.S.; Rubtsov, M.A.; Novikova, L.A.
Expression of cholesterol hydroxylase/lyase system proteins in yeast S. cerevisiae cells as a self-processing polyprotein
Mol. Biotechnol.
59
394-406
2017
Bos taurus (P00189), Bos taurus
Zhang, X.; Liu, Y.; Wang, Y.
The influence of the adjacent hydrogen bond on the hydroxylation processes mediated by cytochrome P450 side-chain cleavage enzyme
Theoret. Chem. Accounts
133
1-8
2014
synthetic construct
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