UniProtKB - Q9HBI6 (CP4FB_HUMAN)
Cytochrome P450 4F11
CYP4F11
Functioni
A cytochrome P450 monooxygenase involved in the metabolism of various endogenous substrates, including fatty acids and their oxygenated derivatives (oxylipins) (PubMed:24138531, PubMed:15364545, PubMed:18065749).
Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (CPR; NADPH-ferrihemoprotein reductase) (PubMed:15364545, PubMed:18065749, PubMed:24138531).
Catalyzes with high efficiency the oxidation of the terminal carbon (omega-oxidation) of 3-hydroxy fatty acids, such as 3-hydroxyhexadecanoic and 3-hydroxyoctadecanoic acids, likely participating in the biosynthesis of long-chain 3-hydroxydicarboxylic acids (PubMed:18065749, PubMed:19932081).
Omega-hydroxylates and inactivates phylloquinone (vitamin K1), and menaquinone-4 (MK-4, a form of vitamin K2), both acting as cofactors in blood coagulation (PubMed:24138531).
Metabolizes with low efficiciency fatty acids, including (5Z,8Z,11Z,14Z)-eicosatetraenoic acid (arachidonate) and its oxygenated metabolite 8-hydroxyeicosatetraenoic acid (8-HETE) (PubMed:15364545, PubMed:19932081).
Catalyzes N- and O-demethylation of drugs such as erythromycin, benzphetamine, ethylmorphine, chlorpromazine, imipramine and verapamil (PubMed:15364545).
4 PublicationsCatalytic activityi
- an organic molecule + O2 + reduced [NADPH—hemoprotein reductase] = an alcohol + H+ + H2O + oxidized [NADPH—hemoprotein reductase]4 PublicationsEC:1.14.14.14 PublicationsThis reaction proceeds in the forward3 Publications direction.
- an ω-methyl-long-chain fatty acid + O2 + reduced [NADPH—hemoprotein reductase] = an ω-hydroxy-long-chain fatty acid + H+ + H2O + oxidized [NADPH—hemoprotein reductase]1 PublicationEC:1.14.14.801 PublicationThis reaction proceeds in the forward1 Publication direction.
- dodecanoate + O2 + reduced [NADPH—hemoprotein reductase] = 12-hydroxydodecanoate + H+ + H2O + oxidized [NADPH—hemoprotein reductase]1 PublicationThis reaction proceeds in the forward1 Publication direction.
- hexadecanoate + O2 + reduced [NADPH—hemoprotein reductase] = 16-hydroxyhexadecanoate + H+ + H2O + oxidized [NADPH—hemoprotein reductase]1 PublicationEC:1.14.14.801 PublicationThis reaction proceeds in the forward1 Publication direction.
- (9Z)-octadecenoate + O2 + reduced [NADPH—hemoprotein reductase] = 18-hydroxy-(9Z)-octadecenoate + H+ + H2O + oxidized [NADPH—hemoprotein reductase]1 PublicationEC:1.14.14.801 PublicationThis reaction proceeds in the forward1 Publication direction.
- (5Z,8Z,11Z,14Z)-eicosatetraenoate + O2 + reduced [NADPH—hemoprotein reductase] = 20-hydroxy-(5Z,8Z,11Z,14Z)-eicosatetraenoate + H+ + H2O + oxidized [NADPH—hemoprotein reductase]1 PublicationThis reaction proceeds in the forward1 Publication direction.
- (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + O2 + reduced [NADPH—hemoprotein reductase] = 22-hydroxy-(4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate + H+ + H2O + oxidized [NADPH—hemoprotein reductase]1 PublicationEC:1.14.14.791 PublicationThis reaction proceeds in the forward1 Publication direction.
- 8-hydroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate + O2 + reduced [NADPH—hemoprotein reductase] = 8,20-dihydroxy-(5Z,9E,11Z,14Z)-eicosatetraenoate + H+ + H2O + oxidized [NADPH—hemoprotein reductase]1 PublicationThis reaction proceeds in the forward1 Publication direction.
- 3-hydroxyhexadecanoate + O2 + reduced [NADPH—hemoprotein reductase] = 3,16-dihydroxyhexadecanoate + H+ + H2O + oxidized [NADPH—hemoprotein reductase]2 PublicationsThis reaction proceeds in the forward2 Publications direction.
- 3-hydroxyoctadecanoate + O2 + reduced [NADPH—hemoprotein reductase] = 3,18-dihydroxyoctadecanoate + H+ + H2O + oxidized [NADPH—hemoprotein reductase]1 PublicationThis reaction proceeds in the forward1 Publication direction.
- O2 + phylloquinone + reduced [NADPH—hemoprotein reductase] = H+ + H2O + ω-hydroxyphylloquinone + oxidized [NADPH—hemoprotein reductase]1 PublicationEC:1.14.14.781 PublicationThis reaction proceeds in the forward1 Publication direction.
- menaquinone-4 + O2 + reduced [NADPH—hemoprotein reductase] = H+ + H2O + ω-hydroxymenaquinone-4 + oxidized [NADPH—hemoprotein reductase]1 PublicationEC:1.14.14.781 PublicationThis reaction proceeds in the forward1 Publication direction.
Cofactori
Kineticsi
- KM=47 µM for hexadecanoic acid1 Publication
- KM=85 µM for (9Z)-octadecenoic acid (oleate)1 Publication
- KM=80 µM for (5Z,8Z,11Z,14Z)-eicosatetraenoic acid1 Publication
- KM=48 µM for (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoic acid1 Publication
- KM=74 µM for 3-hydroxyhexadecanoic acid1 Publication
- KM=105.8 µM for 3-hydroxyhexadecanoic acid1 Publication
- KM=53.5 µM for 3-hydroxyoctadecanoic acid1 Publication
- KM=2.4 µM for menaquinone-4 (MK-4)1 Publication
- KM=125 µM for erythromycin1 Publication
- Vmax=830 pmol/min/ng enzyme with erythromycin as substrate1 Publication
: arachidonate metabolism Pathwayi
This protein is involved in the pathway arachidonate metabolism, which is part of Lipid metabolism.1 PublicationView all proteins of this organism that are known to be involved in the pathway arachidonate metabolism and in Lipid metabolism.
Pathwayi: oxylipin biosynthesis
This protein is involved in the pathway oxylipin biosynthesis, which is part of Lipid metabolism.1 PublicationView all proteins of this organism that are known to be involved in the pathway oxylipin biosynthesis and in Lipid metabolism.
Pathwayi: phylloquinone degradation
This protein is involved in the pathway phylloquinone degradation, which is part of Cofactor degradation.1 PublicationView all proteins of this organism that are known to be involved in the pathway phylloquinone degradation and in Cofactor degradation.
Pathwayi: Xenobiotic degradation
This protein is involved in Xenobiotic degradation.1 PublicationView all proteins of this organism that are known to be involved in Xenobiotic degradation.
Sites
Feature key | Position(s) | DescriptionActions | Graphical view | Length |
---|---|---|---|---|
Binding sitei | 328 | Heme; covalent, via 1 linkBy similarity | 1 | |
Metal bindingi | 468 | Iron (heme axial ligand)By similarity | 1 |
GO - Molecular functioni
- arachidonic acid monooxygenase activity Source: GO_Central
- aromatase activity Source: UniProtKB-EC
- fatty acid binding Source: BHF-UCL
- heme binding Source: InterPro
- iron ion binding Source: InterPro
- leukotriene-B4 20-monooxygenase activity Source: GO_Central
- long-chain fatty acid omega-hydroxylase activity Source: UniProtKB
- monooxygenase activity Source: Reactome
- oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, NAD(P)H as one donor, and incorporation of one atom of oxygen Source: UniProtKB
GO - Biological processi
- arachidonic acid metabolic process Source: GO_Central
- blood coagulation Source: UniProtKB
- fatty acid metabolic process Source: BHF-UCL
- leukotriene B4 catabolic process Source: GO_Central
- menaquinone catabolic process Source: UniProtKB
- omega-hydroxylase P450 pathway Source: UniProtKB
- oxylipin biosynthetic process Source: UniProtKB-UniPathway
- phylloquinone catabolic process Source: UniProtKB
- vitamin K catabolic process Source: UniProtKB
Keywordsi
Molecular function | Monooxygenase, Oxidoreductase |
Biological process | Fatty acid metabolism, Lipid metabolism |
Ligand | Heme, Iron, Metal-binding, NADP |
Enzyme and pathway databases
PathwayCommonsi | Q9HBI6 |
Reactomei | R-HSA-211935, Fatty acids R-HSA-211958, Miscellaneous substrates R-HSA-211979, Eicosanoids R-HSA-2142691, Synthesis of Leukotrienes (LT) and Eoxins (EX) |
SignaLinki | Q9HBI6 |
UniPathwayi | UPA00382 UPA00383 UPA01054 |
Chemistry databases
SwissLipidsi | SLP:000000470 |
Names & Taxonomyi
Protein namesi | Recommended name: Cytochrome P450 4F111 Publication (EC:1.14.14.13 Publications)Short name: CYPIVF11 Alternative name(s): 3-hydroxy fatty acids omega-hydroxylase CYP4F111 Publication Docosahexaenoic acid omega-hydroxylase1 Publication (EC:1.14.14.791 Publication) Long-chain fatty acid omega-monooxygenase1 Publication (EC:1.14.14.801 Publication) Phylloquinone omega-hydroxylase CYP4F111 Publication (EC:1.14.14.781 Publication) |
Gene namesi | |
Organismi | Homo sapiens (Human) |
Taxonomic identifieri | 9606 [NCBI] |
Taxonomic lineagei | Eukaryota › Metazoa › Chordata › Craniata › Vertebrata › Euteleostomi › Mammalia › Eutheria › Euarchontoglires › Primates › Haplorrhini › Catarrhini › Hominidae › Homo |
Proteomesi |
|
Organism-specific databases
HGNCi | HGNC:13265, CYP4F11 |
MIMi | 611517, gene |
neXtProti | NX_Q9HBI6 |
VEuPathDBi | HostDB:ENSG00000171903 |
Subcellular locationi
Endoplasmic reticulum
- Endoplasmic reticulum membrane 1 Publication; Single-pass membrane protein Curated
- Microsome membrane 1 Publication; Single-pass membrane protein Curated
Endoplasmic reticulum
- endoplasmic reticulum membrane Source: Reactome
Other locations
- integral component of membrane Source: UniProtKB-KW
- intracellular membrane-bounded organelle Source: GO_Central
Topology
Feature key | Position(s) | DescriptionActions | Graphical view | Length |
---|---|---|---|---|
Transmembranei | 15 – 37 | HelicalSequence analysisAdd BLAST | 23 |
Keywords - Cellular componenti
Endoplasmic reticulum, Membrane, MicrosomePathology & Biotechi
Organism-specific databases
DisGeNETi | 57834 |
OpenTargetsi | ENSG00000171903 |
PharmGKBi | PA27120 |
Miscellaneous databases
Pharosi | Q9HBI6, Tbio |
Chemistry databases
ChEMBLi | CHEMBL4295949 |
Genetic variation databases
BioMutai | CYP4F11 |
DMDMi | 296439388 |
PTM / Processingi
Molecule processing
Feature key | Position(s) | DescriptionActions | Graphical view | Length |
---|---|---|---|---|
ChainiPRO_0000051856 | 1 – 524 | Cytochrome P450 4F11Add BLAST | 524 |
Proteomic databases
EPDi | Q9HBI6 |
jPOSTi | Q9HBI6 |
MassIVEi | Q9HBI6 |
MaxQBi | Q9HBI6 |
PaxDbi | Q9HBI6 |
PeptideAtlasi | Q9HBI6 |
PRIDEi | Q9HBI6 |
ProteomicsDBi | 81562 |
PTM databases
iPTMneti | Q9HBI6 |
PhosphoSitePlusi | Q9HBI6 |
Expressioni
Tissue specificityi
Gene expression databases
Bgeei | ENSG00000171903, Expressed in liver and 123 other tissues |
ExpressionAtlasi | Q9HBI6, baseline and differential |
Genevisiblei | Q9HBI6, HS |
Organism-specific databases
HPAi | ENSG00000171903, Tissue enhanced (intestine, liver) |
Interactioni
Binary interactionsi
Q9HBI6
With | #Exp. | IntAct |
---|---|---|
MESD [Q14696] | 3 | EBI-3924028,EBI-6165891 |
Protein-protein interaction databases
BioGRIDi | 121790, 12 interactors |
IntActi | Q9HBI6, 2 interactors |
STRINGi | 9606.ENSP00000384588 |
Miscellaneous databases
RNActi | Q9HBI6, protein |
Family & Domainsi
Sequence similaritiesi
Keywords - Domaini
Transmembrane, Transmembrane helixPhylogenomic databases
eggNOGi | KOG0157, Eukaryota |
GeneTreei | ENSGT00940000164421 |
HOGENOMi | CLU_001570_5_1_1 |
InParanoidi | Q9HBI6 |
OMAi | IQPAFRL |
OrthoDBi | 1247045at2759 |
PhylomeDBi | Q9HBI6 |
TreeFami | TF105088 |
Family and domain databases
Gene3Di | 1.10.630.10, 1 hit |
InterProi | View protein in InterPro IPR001128, Cyt_P450 IPR017972, Cyt_P450_CS IPR002401, Cyt_P450_E_grp-I IPR036396, Cyt_P450_sf |
Pfami | View protein in Pfam PF00067, p450, 1 hit |
PRINTSi | PR00463, EP450I PR00385, P450 |
SUPFAMi | SSF48264, SSF48264, 1 hit |
PROSITEi | View protein in PROSITE PS00086, CYTOCHROME_P450, 1 hit |
(1+)i Sequence
Sequence statusi: Complete.
This entry has 1 described isoform and 2 potential isoforms that are computationally mapped.Show allAlign All
10 20 30 40 50
MPQLSLSWLG LGPVAASPWL LLLLVGGSWL LARVLAWTYT FYDNCRRLQC
60 70 80 90 100
FPQPPKQNWF WGHQGLVTPT EEGMKTLTQL VTTYPQGFKL WLGPTFPLLI
110 120 130 140 150
LCHPDIIRPI TSASAAVAPK DMIFYGFLKP WLGDGLLLSG GDKWSRHRRM
160 170 180 190 200
LTPAFHFNIL KPYMKIFNKS VNIMHDKWQR LASEGSARLD MFEHISLMTL
210 220 230 240 250
DSLQKCVFSF ESNCQEKPSE YIAAILELSA FVEKRNQQIL LHTDFLYYLT
260 270 280 290 300
PDGQRFRRAC HLVHDFTDAV IQERRCTLPT QGIDDFLKNK AKSKTLDFID
310 320 330 340 350
VLLLSKDEDG KELSDEDIRA EADTFMFEGH DTTASGLSWV LYHLAKHPEY
360 370 380 390 400
QEQCRQEVQE LLKDREPIEI EWDDLAQLPF LTMCIKESLR LHPPVPVISR
410 420 430 440 450
CCTQDFVLPD GRVIPKGIVC LINIIGIHYN PTVWPDPEVY DPFRFDQENI
460 470 480 490 500
KERSPLAFIP FSAGPRNCIG QAFAMAEMKV VLALTLLHFR ILPTHTEPRR
510 520
KPELILRAEG GLWLRVEPLG ANSQ
Computationally mapped potential isoform sequencesi
There are 2 potential isoforms mapped to this entry.BLASTAlignShow allAdd to basketF8W978 | F8W978_HUMAN | Cytochrome P450 4F11 | CYP4F11 | 454 | Annotation score: | ||
V9GYP6 | V9GYP6_HUMAN | Cytochrome P450 4F11 | CYP4F11 | 199 | Annotation score: |
Sequence cautioni
Experimental Info
Feature key | Position(s) | DescriptionActions | Graphical view | Length |
---|---|---|---|---|
Sequence conflicti | 458 | F → L in BAF82113 (PubMed:14702039).Curated | 1 | |
Sequence conflicti | 496 | T → I in AAG15889 (PubMed:10964514).Curated | 1 |
Natural variant
Feature key | Position(s) | DescriptionActions | Graphical view | Length |
---|---|---|---|---|
Natural variantiVAR_060265 | 146 | R → C. Corresponds to variant dbSNP:rs57519667Ensembl. | 1 | |
Natural variantiVAR_060266 | 276 | C → R4 PublicationsCorresponds to variant dbSNP:rs8104361Ensembl. | 1 | |
Natural variantiVAR_071198 | 446 | D → N Does not affect enzyme activity. 4 PublicationsCorresponds to variant dbSNP:rs1060463Ensembl. | 1 |
Sequence databases
Select the link destinations: EMBLi GenBanki DDBJi Links Updated | AF236085 mRNA Translation: AAG15889.1 AK289424 mRNA Translation: BAF82113.1 AC005336 Genomic DNA Translation: AAC27731.1 Sequence problems. AC020950 Genomic DNA No translation available. AC011517 Genomic DNA No translation available. CH471106 Genomic DNA Translation: EAW84512.1 CH471106 Genomic DNA Translation: EAW84513.1 BC016853 mRNA Translation: AAH16853.1 |
CCDSi | CCDS12337.1 |
RefSeqi | NP_001122404.1, NM_001128932.1 NP_067010.3, NM_021187.3 |
Genome annotation databases
Ensembli | ENST00000248041; ENSP00000248041; ENSG00000171903 ENST00000402119; ENSP00000384588; ENSG00000171903 |
GeneIDi | 57834 |
KEGGi | hsa:57834 |
MANE-Selecti | ENST00000402119.9; ENSP00000384588.2; NM_021187.4; NP_067010.3 |
UCSCi | uc002nbt.3, human |
Similar proteinsi
Cross-referencesi
Sequence databases
Select the link destinations: EMBLi GenBanki DDBJi Links Updated | AF236085 mRNA Translation: AAG15889.1 AK289424 mRNA Translation: BAF82113.1 AC005336 Genomic DNA Translation: AAC27731.1 Sequence problems. AC020950 Genomic DNA No translation available. AC011517 Genomic DNA No translation available. CH471106 Genomic DNA Translation: EAW84512.1 CH471106 Genomic DNA Translation: EAW84513.1 BC016853 mRNA Translation: AAH16853.1 |
CCDSi | CCDS12337.1 |
RefSeqi | NP_001122404.1, NM_001128932.1 NP_067010.3, NM_021187.3 |
3D structure databases
SMRi | Q9HBI6 |
ModBasei | Search... |
Protein-protein interaction databases
BioGRIDi | 121790, 12 interactors |
IntActi | Q9HBI6, 2 interactors |
STRINGi | 9606.ENSP00000384588 |
Chemistry databases
ChEMBLi | CHEMBL4295949 |
SwissLipidsi | SLP:000000470 |
PTM databases
iPTMneti | Q9HBI6 |
PhosphoSitePlusi | Q9HBI6 |
Genetic variation databases
BioMutai | CYP4F11 |
DMDMi | 296439388 |
Proteomic databases
EPDi | Q9HBI6 |
jPOSTi | Q9HBI6 |
MassIVEi | Q9HBI6 |
MaxQBi | Q9HBI6 |
PaxDbi | Q9HBI6 |
PeptideAtlasi | Q9HBI6 |
PRIDEi | Q9HBI6 |
ProteomicsDBi | 81562 |
Protocols and materials databases
Antibodypediai | 2634, 158 antibodies from 29 providers |
DNASUi | 57834 |
Genome annotation databases
Ensembli | ENST00000248041; ENSP00000248041; ENSG00000171903 ENST00000402119; ENSP00000384588; ENSG00000171903 |
GeneIDi | 57834 |
KEGGi | hsa:57834 |
MANE-Selecti | ENST00000402119.9; ENSP00000384588.2; NM_021187.4; NP_067010.3 |
UCSCi | uc002nbt.3, human |
Organism-specific databases
CTDi | 57834 |
DisGeNETi | 57834 |
GeneCardsi | CYP4F11 |
HGNCi | HGNC:13265, CYP4F11 |
HPAi | ENSG00000171903, Tissue enhanced (intestine, liver) |
MIMi | 611517, gene |
neXtProti | NX_Q9HBI6 |
OpenTargetsi | ENSG00000171903 |
PharmGKBi | PA27120 |
VEuPathDBi | HostDB:ENSG00000171903 |
GenAtlasi | Search... |
Phylogenomic databases
eggNOGi | KOG0157, Eukaryota |
GeneTreei | ENSGT00940000164421 |
HOGENOMi | CLU_001570_5_1_1 |
InParanoidi | Q9HBI6 |
OMAi | IQPAFRL |
OrthoDBi | 1247045at2759 |
PhylomeDBi | Q9HBI6 |
TreeFami | TF105088 |
Enzyme and pathway databases
UniPathwayi | UPA00382 UPA00383 UPA01054 |
PathwayCommonsi | Q9HBI6 |
Reactomei | R-HSA-211935, Fatty acids R-HSA-211958, Miscellaneous substrates R-HSA-211979, Eicosanoids R-HSA-2142691, Synthesis of Leukotrienes (LT) and Eoxins (EX) |
SignaLinki | Q9HBI6 |
Miscellaneous databases
BioGRID-ORCSi | 57834, 68 hits in 1034 CRISPR screens |
ChiTaRSi | CYP4F11, human |
GeneWikii | CYP4F11 |
GenomeRNAii | 57834 |
Pharosi | Q9HBI6, Tbio |
PROi | PR:Q9HBI6 |
RNActi | Q9HBI6, protein |
SOURCEi | Search... |
Gene expression databases
Bgeei | ENSG00000171903, Expressed in liver and 123 other tissues |
ExpressionAtlasi | Q9HBI6, baseline and differential |
Genevisiblei | Q9HBI6, HS |
Family and domain databases
Gene3Di | 1.10.630.10, 1 hit |
InterProi | View protein in InterPro IPR001128, Cyt_P450 IPR017972, Cyt_P450_CS IPR002401, Cyt_P450_E_grp-I IPR036396, Cyt_P450_sf |
Pfami | View protein in Pfam PF00067, p450, 1 hit |
PRINTSi | PR00463, EP450I PR00385, P450 |
SUPFAMi | SSF48264, SSF48264, 1 hit |
PROSITEi | View protein in PROSITE PS00086, CYTOCHROME_P450, 1 hit |
MobiDBi | Search... |
Entry informationi
Entry namei | CP4FB_HUMAN | |
Accessioni | Q9HBI6Primary (citable) accession number: Q9HBI6 Secondary accession number(s): A0A024R7G0 Q96AQ5 | |
Entry historyi | Integrated into UniProtKB/Swiss-Prot: | May 10, 2002 |
Last sequence update: | May 18, 2010 | |
Last modified: | February 23, 2022 | |
This is version 177 of the entry and version 3 of the sequence. See complete history. | ||
Entry statusi | Reviewed (UniProtKB/Swiss-Prot) | |
Annotation program | Chordata Protein Annotation Program | |
Disclaimer | Any medical or genetic information present in this entry is provided for research, educational and informational purposes only. It is not in any way intended to be used as a substitute for professional medical advice, diagnosis, treatment or care. |
Miscellaneousi
Keywords - Technical termi
Reference proteomeDocuments
- Human chromosome 19
Human chromosome 19: entries, gene names and cross-references to MIM - Human entries with genetic variants
List of human entries with genetic variants - Human variants curated from literature reports
Index of human variants curated from literature reports - MIM cross-references
Online Mendelian Inheritance in Man (MIM) cross-references in UniProtKB/Swiss-Prot - PATHWAY comments
Index of metabolic and biosynthesis pathways - SIMILARITY comments
Index of protein domains and families