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CP181_THYVU
ID   CP181_THYVU             Reviewed;         496 AA.
AC   P0DO42;
DT   29-SEP-2021, integrated into UniProtKB/Swiss-Prot.
DT   29-SEP-2021, sequence version 1.
DT   03-AUG-2022, entry version 4.
DE   RecName: Full=Cytochrome P450 71D181 {ECO:0000303|Ref.1};
DE   AltName: Full=Alpha-terpinene hydroxylase {ECO:0000305|Ref.1};
DE   AltName: Full=Carvacrol synthase {ECO:0000305|Ref.1};
DE            EC=1.14.14.- {ECO:0000269|Ref.1};
DE   AltName: Full=Carveol synthase {ECO:0000305|Ref.1};
DE            EC=1.14.14.51 {ECO:0000269|Ref.1};
DE            EC=1.14.14.53 {ECO:0000269|Ref.1};
DE   AltName: Full=Gamma-terpinene hydroxylase {ECO:0000305|Ref.1};
DE   AltName: Full=Limonene hydroxylase {ECO:0000305|Ref.1};
GN   Name=CYP71D181 {ECO:0000303|Ref.1};
OS   Thymus vulgaris (Thyme).
OC   Eukaryota; Viridiplantae; Streptophyta; Embryophyta; Tracheophyta;
OC   Spermatophyta; Magnoliopsida; eudicotyledons; Gunneridae; Pentapetalae;
OC   asterids; lamiids; Lamiales; Lamiaceae; Nepetoideae; Mentheae; Thymus.
OX   NCBI_TaxID=49992;
RN   [1]
RP   NUCLEOTIDE SEQUENCE [MRNA], FUNCTION, CATALYTIC ACTIVITY, PATHWAY, AND
RP   BIOPHYSICOCHEMICAL PROPERTIES.
RC   STRAIN=cv. Tc; TISSUE=Leaf;
RA   Crocoll C.;
RT   "Biosynthesis of the phenolic monoterpenes, thymol and carvacrol, by
RT   terpene synthases and cytochrome P450s in oregano and thyme.";
RL   Thesis (2011), Friedrich Schiller University of Jena, Germany.
RN   [2]
RP   REVIEW ON CARVACROL, AND BIOTECHNOLOGY.
RX   PubMed=24915411; DOI=10.1080/10408398.2011.653458;
RA   Suntres Z.E., Coccimiglio J., Alipour M.;
RT   "The bioactivity and toxicological actions of carvacrol.";
RL   Crit. Rev. Food Sci. Nutr. 55:304-318(2015).
RN   [3]
RP   REVIEW ON THYMOL, AND BIOTECHNOLOGY.
RX   PubMed=29785774; DOI=10.1002/ptr.6109;
RA   Salehi B., Mishra A.P., Shukla I., Sharifi-Rad M., Contreras M.D.M.,
RA   Segura-Carretero A., Fathi H., Nasrabadi N.N., Kobarfard F.,
RA   Sharifi-Rad J.;
RT   "Thymol, thyme, and other plant sources: Health and potential uses.";
RL   Phytother. Res. 32:1688-1706(2018).
RN   [4]
RP   REVIEW ON CARVACROL AND THYMOL, AND BIOTECHNOLOGY.
RX   PubMed=29874939; DOI=10.1080/14786419.2018.1480618;
RA   Wang K., Jiang S., Yang Y., Fan L., Su F., Ye M.;
RT   "Synthesis and antifungal activity of carvacrol and thymol esters with
RT   heteroaromatic carboxylic acids.";
RL   Nat. Prod. Res. 33:1924-1930(2019).
RN   [5]
RP   REVIEW ON CARVACROL EFFECTS ON COVID-19, AND BIOTECHNOLOGY.
RX   PubMed=33664752; DOI=10.3389/fpls.2020.601335;
RA   Javed H., Meeran M.F.N., Jha N.K., Ojha S.;
RT   "Carvacrol, a plant metabolite targeting viral protease (Mpro) and ACE2 in
RT   host cells can be a possible candidate for COVID-19.";
RL   Front. Plant Sci. 11:601335-601335(2020).
RN   [6]
RP   REVIEW ON CARVACROL EFFECTS ON COVID-19, AND BIOTECHNOLOGY.
RX   PubMed=32448034; DOI=10.1080/07391102.2020.1772112;
RA   Kumar A., Choudhir G., Shukla S.K., Sharma M., Tyagi P., Bhushan A.,
RA   Rathore M.;
RT   "Identification of phytochemical inhibitors against main protease of COVID-
RT   19 using molecular modeling approaches.";
RL   J. Biomol. Struct. Dyn. 4:1-11(2020).
RN   [7]
RP   REVIEW ON CARVACROL DERIVATIVES, AND BIOTECHNOLOGY.
RX   PubMed=30836858; DOI=10.1080/07391102.2019.1590243;
RA   Zengin Kurt B., Durdagi S., Celebi G., Ekhteiari Salmas R., Sonmez F.;
RT   "Synthesis, anticholinesterase activity and molecular modeling studies of
RT   novel carvacrol-substituted amide derivatives.";
RL   J. Biomol. Struct. Dyn. 38:841-859(2020).
RN   [8]
RP   REVIEW ON PLANT ESSENTIAL OILS EFFECTS ON COVID-19, AND BIOTECHNOLOGY.
RX   PubMed=32834111; DOI=10.1016/j.molstruc.2020.128823;
RA   Kulkarni S.A., Nagarajan S.K., Ramesh V., Palaniyandi V., Selvam S.P.,
RA   Madhavan T.;
RT   "Computational evaluation of major components from plant essential oils as
RT   potent inhibitors of SARS-CoV-2 spike protein.";
RL   J. Mol. Struct. 1221:128823-128823(2020).
RN   [9]
RP   REVIEW ON PLANT ESSENTIAL OILS EFFECTS ON COVID-19, AND BIOTECHNOLOGY.
RX   PubMed=33855010; DOI=10.3389/fchem.2021.642026;
RA   Yadalam P.K., Varatharajan K., Rajapandian K., Chopra P., Arumuganainar D.,
RA   Nagarathnam T., Sohn H., Madhavan T.;
RT   "Antiviral essential oil components against SARS-CoV-2 in pre-procedural
RT   mouth rinses for dental settings during COVID-19: A computational study.";
RL   Front. Chem. 9:642026-642026(2021).
CC   -!- FUNCTION: Involved in the biosynthesis of phenolic monoterpenes natural
CC       products thymol and carvacrol which have a broad range of biological
CC       activities acting as antimicrobial compounds, insecticides,
CC       antioxidants and pharmaceutical agents (Ref.1). Catalyzes the C2-
CC       hydroxylation of gamma-terpinene and alpha-terpinene to produce
CC       carvacrol (Ref.1). Mediates also the C6-hydroxylation of (4S)-limonene
CC       and (4R)-limonene to form carveol (Ref.1). {ECO:0000269|Ref.1}.
CC   -!- CATALYTIC ACTIVITY:
CC       Reaction=gamma-terpinene + 2 O2 + 2 reduced [NADPH--hemoprotein
CC         reductase] = carvacrol + 2 H(+) + 3 H2O + 2 oxidized [NADPH--
CC         hemoprotein reductase]; Xref=Rhea:RHEA:67404, Rhea:RHEA-COMP:11964,
CC         Rhea:RHEA-COMP:11965, ChEBI:CHEBI:3440, ChEBI:CHEBI:10577,
CC         ChEBI:CHEBI:15377, ChEBI:CHEBI:15378, ChEBI:CHEBI:15379,
CC         ChEBI:CHEBI:57618, ChEBI:CHEBI:58210; Evidence={ECO:0000269|Ref.1};
CC       PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:67405;
CC         Evidence={ECO:0000269|Ref.1};
CC   -!- CATALYTIC ACTIVITY:
CC       Reaction=(4S)-limonene + O2 + reduced [NADPH--hemoprotein reductase] =
CC         (1S,5R)-carveol + H(+) + H2O + oxidized [NADPH--hemoprotein
CC         reductase]; Xref=Rhea:RHEA:17945, Rhea:RHEA-COMP:11964, Rhea:RHEA-
CC         COMP:11965, ChEBI:CHEBI:15377, ChEBI:CHEBI:15378, ChEBI:CHEBI:15379,
CC         ChEBI:CHEBI:15383, ChEBI:CHEBI:15389, ChEBI:CHEBI:57618,
CC         ChEBI:CHEBI:58210; EC=1.14.14.51; Evidence={ECO:0000269|Ref.1};
CC       PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:17946;
CC         Evidence={ECO:0000269|Ref.1};
CC   -!- CATALYTIC ACTIVITY:
CC       Reaction=(4R)-limonene + O2 + reduced [NADPH--hemoprotein reductase] =
CC         (1R,5S)-carveol + H(+) + H2O + oxidized [NADPH--hemoprotein
CC         reductase]; Xref=Rhea:RHEA:18957, Rhea:RHEA-COMP:11964, Rhea:RHEA-
CC         COMP:11965, ChEBI:CHEBI:15377, ChEBI:CHEBI:15378, ChEBI:CHEBI:15379,
CC         ChEBI:CHEBI:15382, ChEBI:CHEBI:15388, ChEBI:CHEBI:57618,
CC         ChEBI:CHEBI:58210; EC=1.14.14.53; Evidence={ECO:0000269|Ref.1};
CC       PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:18958;
CC         Evidence={ECO:0000269|Ref.1};
CC   -!- CATALYTIC ACTIVITY:
CC       Reaction=alpha-terpinene + 2 O2 + 2 reduced [NADPH--hemoprotein
CC         reductase] = carvacrol + 2 H(+) + 3 H2O + 2 oxidized [NADPH--
CC         hemoprotein reductase]; Xref=Rhea:RHEA:67412, Rhea:RHEA-COMP:11964,
CC         Rhea:RHEA-COMP:11965, ChEBI:CHEBI:3440, ChEBI:CHEBI:10334,
CC         ChEBI:CHEBI:15377, ChEBI:CHEBI:15378, ChEBI:CHEBI:15379,
CC         ChEBI:CHEBI:57618, ChEBI:CHEBI:58210; Evidence={ECO:0000269|Ref.1};
CC       PhysiologicalDirection=left-to-right; Xref=Rhea:RHEA:67413;
CC         Evidence={ECO:0000269|Ref.1};
CC   -!- COFACTOR:
CC       Name=heme; Xref=ChEBI:CHEBI:30413;
CC         Evidence={ECO:0000250|UniProtKB:Q96242};
CC   -!- BIOPHYSICOCHEMICAL PROPERTIES:
CC       pH dependence:
CC         Optimum pH is 6.8-7. {ECO:0000269|Ref.1};
CC   -!- PATHWAY: Secondary metabolite biosynthesis; terpenoid biosynthesis.
CC       {ECO:0000269|Ref.1}.
CC   -!- SUBCELLULAR LOCATION: Membrane {ECO:0000255}; Single-pass type II
CC       membrane protein {ECO:0000305}.
CC   -!- BIOTECHNOLOGY: The monoterpenic phenol thymol is widely used as a
CC       fragrance and a flavoring ingredient in food and cosmetic industries
CC       (PubMed:29785774). Its derivatives have also several biological and
CC       pharmacological properties such as antimicrobial, antioxidant,
CC       anticarcinogenesis, anti-inflammatory and antispasmodic activities
CC       (PubMed:29785774, PubMed:29874939). Medical applications include the
CC       treatment of disorders affecting the respiratory, nervous, and
CC       cardiovascular systems (PubMed:29785774). It may also act as a growth
CC       enhancer and immunomodulator (PubMed:29785774). Thymol may also have
CC       antiviral activity toward COVID-19 by binding to the S1 receptor
CC       binding domain of the SARS-CoV-2 spike (S) glycoprotein
CC       (PubMed:32834111, PubMed:33855010). {ECO:0000303|PubMed:29785774,
CC       ECO:0000303|PubMed:29874939, ECO:0000303|PubMed:32834111,
CC       ECO:0000303|PubMed:33855010}.
CC   -!- BIOTECHNOLOGY: The monoterpenic phenol carvacrol is commonly used as a
CC       fragrance and a food flavoring ingredient and preservative
CC       (PubMed:24915411). Its derivatives exhibit also various biological and
CC       pharmacological properties including antioxidant, antibacterial,
CC       antifungal, insecticid, nematicid, anticancer, anti-inflammatory,
CC       hepatoprotective, spasmolytic, and vasorelaxant (PubMed:24915411,
CC       PubMed:29874939, PubMed:30836858, PubMed:33664752). Phytochemical
CC       inhibitor targeting the main SARS-CoV-2 viral protease (Mpro) and ACE2
CC       in human host cells, carvacrol is a possible candidate for treating
CC       COVID-19 (PubMed:33664752, PubMed:32448034). Carvacrol may also have
CC       antiviral activity toward COVID-19 by binding to the S1 receptor
CC       binding domain of the SARS-CoV-2 spike (S) glycoprotein
CC       (PubMed:32834111, PubMed:33855010). {ECO:0000303|PubMed:24915411,
CC       ECO:0000303|PubMed:29874939, ECO:0000303|PubMed:30836858,
CC       ECO:0000303|PubMed:32448034, ECO:0000303|PubMed:32834111,
CC       ECO:0000303|PubMed:33664752, ECO:0000303|PubMed:33855010}.
CC   -!- SIMILARITY: Belongs to the cytochrome P450 family. {ECO:0000305}.
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DR   SMR; P0DO42; -.
DR   UniPathway; UPA00213; -.
DR   GO; GO:0016021; C:integral component of membrane; IEA:UniProtKB-KW.
DR   GO; GO:0020037; F:heme binding; IEA:InterPro.
DR   GO; GO:0005506; F:iron ion binding; IEA:InterPro.
DR   GO; GO:0004497; F:monooxygenase activity; IEA:UniProtKB-KW.
DR   GO; GO:0016705; F:oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen; IEA:InterPro.
DR   GO; GO:0016114; P:terpenoid biosynthetic process; IEA:UniProtKB-UniPathway.
DR   Gene3D; 1.10.630.10; -; 1.
DR   InterPro; IPR001128; Cyt_P450.
DR   InterPro; IPR017972; Cyt_P450_CS.
DR   InterPro; IPR002401; Cyt_P450_E_grp-I.
DR   InterPro; IPR036396; Cyt_P450_sf.
DR   Pfam; PF00067; p450; 1.
DR   PRINTS; PR00463; EP450I.
DR   PRINTS; PR00385; P450.
DR   SUPFAM; SSF48264; SSF48264; 1.
DR   PROSITE; PS00086; CYTOCHROME_P450; 1.
PE   1: Evidence at protein level;
KW   Heme; Iron; Membrane; Metal-binding; Monooxygenase; Oxidoreductase;
KW   Signal-anchor; Transmembrane; Transmembrane helix.
FT   CHAIN           1..496
FT                   /note="Cytochrome P450 71D181"
FT                   /id="PRO_0000453329"
FT   TRANSMEM        1..21
FT                   /note="Helical; Signal-anchor for type II membrane protein"
FT                   /evidence="ECO:0000255"
FT   REGION          471..496
FT                   /note="Disordered"
FT                   /evidence="ECO:0000256|SAM:MobiDB-lite"
FT   BINDING         435
FT                   /ligand="heme"
FT                   /ligand_id="ChEBI:CHEBI:30413"
FT                   /ligand_part="Fe"
FT                   /ligand_part_id="ChEBI:CHEBI:18248"
FT                   /note="axial binding residue"
FT                   /evidence="ECO:0000250|UniProtKB:Q96242"
SQ   SEQUENCE   496 AA;  56034 MW;  9D9C52C37C9632F4 CRC64;
     MDISILWVAI ILVISSYFIF MNKWRAAKLP ENLPPSPPKL PVIGHLHLLR GGLPQHVLRG
     ITQKYGAVAH LQLGEVYSVV LSSAESTKQA MKVLDPTFAD RFDSFGSQIM WYNNNDMIFS
     RYNDHWRQIR KICVSELLSP KNVRSFGFIR QDEMARLIRV FESSVGVPIN ASEEISKMSC
     AIVCRAAFGS VLKDQGLLAD LVKEALGMAS GFELADLYPS SWLLNLLCFN KYRLRRMRQR
     LDDILDGFLE EHRVKKSGEF GGEDIIDVLY RMQKDSENKV PITNSGIKGF IFDVFSAGTE
     TSATTIQWAL SELMKNPEKL AKAQAEVREK LKGKTNPDVA EVQEIKYPHS VVKETLRLHP
     PFPLIPRLCK EECEVTGYTI PAKTRILVNV WSIGRDPAYW KDPDTFNPDR FDEVSRDVIG
     NDFELIPFGA GRRICPGLHF GLANVEVPLA QLLYHFEWKL PQGMTPADMD MSETPGLSGP
     RKNPLIMVPT IHNPTS
 
 
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