Showing information for HMDB0002183 ('docosahexaenoic acid', 'docohexaenoic acid', 'docosahexaenoate')

Metabolite information
HMDB ID HMDB0002183
Synonyms
22:6-4, 7,10,13,16,19
22:6[N-3]
4,7,10,13,16,19-Docosahexaenoate
4,7,10,13,16,19-Docosahexaenoic acid
Acids, docosahexaenoic
Acids, docosahexenoic
Adipose
Body fat
Cellular membrane
Cerebrovascular accident
Cerebrovascular insult
Cervonate
Cervonic acid
Coffee
Coffee bean
Csf
Cucurbits
Cva
Cvi
Cytoplasma
DHA
DOCOSA-4,7,10,13,16,19-hexaenoIC ACID
DOCOSA-4,7,10,13,16,19-hexaenoate
Digestion
Doconexent
Doconexento
Doconexentum
Docosahexaenoate
Docosahexaenoic acid [all-Z isomer]
Docosahexaenoic acid dimer [all-Z isomer]
Docosahexaenoic acid, 3,6,9,12,15,18-isomer
Docosahexaenoic acid, 4,7,10,13,16,19-[Z,Z,Z,Z,Z,e-isomer]
Docosahexaenoic acid, 4,7,10,13,16,19-[all-Z-isomer]
Docosahexaenoic acid, 4,7,10,13,16,19-[all-Z-isomer], cerium salt
Docosahexaenoic acid, 4,7,10,13,16,19-[all-Z-isomer], cesium salt
Docosahexaenoic acid, 4,7,10,13,16,19-[all-Z-isomer], potassium salt
Docosahexaenoic acid, 4,7,10,13,16,19-isomer
Docosahexaenoic acid, 4,7,10,13,16,19-isomer, sodium salt
Docosahexaenoic acid, sodium salt
Docosahexaenoic acids
Docosahexenoic acids
Doxonexent
Eh
Extracellular region
Faecal
Faeces
Fat tissue
Fauna
Fecal
Flora
Gourds
Gramineae
High blood pressure
Hpn
Htn
Kidneys
Legume
Lipid body
Lipid droplet
Lipid metabolic process
Lipid particle
Membrane integrity agent
Membrane stability agent
Myelin
Nerve tissue
Neural tissue
Neuron
Papilionoideae
Primary hypertension
Prostate gland
Signal transduction
Soy
Soya
Soya bean
Soybean
Stool
Striated muscle
Surface-active agent
Testes
Testis
Thrombocyte
[4Z,7Z,10Z,13Z,16Z,19Z]-Docosahexaenoate
[4Z,7Z,10Z,13Z,16Z,19Z]-Docosahexaenoic acid
all-Z-Docosahexaenoate
all-Z-Docosahexaenoic acid
all-cis-4,7,10,13,16,19-Docosahexaenoate
all-cis-4,7,10,13,16,19-Docosahexaenoic acid
all-cis-DHA
cis-4,7,10,13,16,19-Docosahexanoate
cis-4,7,10,13,16,19-Docosahexanoic acid
Chemical formula C22H32O2
IUPAC name
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
CAS registry number 6217-54-5
Monisotopic molecular weight 328.240230268

Chemical taxonomy
Super class Lipids and lipid-like molecules
Class Fatty Acyls
Sub class Fatty acids and conjugates

Biological properties
Pahtways
Alpha Linolenic Acid and Linoleic Acid Metabolism
Author-emphasized biomarker in the paper(s)

Lung cancer metabolomics studies that identify HMDB0002183 ('docosahexaenoic acid', 'docohexaenoic acid', 'docosahexaenoate')

Reference Country Specimen Marker function Participants (Case) Participants (Control)
Cancer type Stage Number Gender (M,F) Age mean (range) (M/F) Smoking status Type Number Gender (M,F) Age mean (range) (M/F) Smoking status
Mazzone et al. 2016 – serum – adenocarcinoma, squamous cell carcinoma I, II, III 94 55.3%, 44.7% 68.7 – at-risk controls 190 50.5%, 49.5% 66.2 –
Roś-Mazurczyk et al. 2017 – serum diagnosis adenocarcinoma, squamous cell carcinoma I, II, III 31 17, 14 52-72 – healthy 92 52, 40 52-73 –
Callejón-Leblic et al. 2019 – blood diagnosis NSCLC, SCLC II, III, IV 30 25, 5 67 ± 12 former, current, non-smoker healthy 30 14, 16 56 ± 14 former, non-smoker
Mu et al. 2019 – serum diagnosis NSCLC I, II, III, IV 30 0, 30 60.4 ± 9.7 non-smoker healthy 30 0, 30 54.7 ± 14.3 non-smoker
Huang et al. 2019 – plasma diagnosis lung cancer – 31 19, 12 28-64 – healthy 35 24, 11 23-60 –
Moreno et al. 2018 – tissue therapy, diagnosis adenocarcinoma I, II, III 33 24, 9 62.11 ± 9.73 – tumor vs. adjacent normal tissue 33 24, 9 62.11 ± 9.73 –
Moreno et al. 2018 – tissue therapy, diagnosis squamous cell carcinoma I, II, III 35 35, 0 68.71 ± 7.46 – tumor vs. adjacent normal tissue 35 35, 0 68.71 ± 7.46 –
Reference Chromatography Ion source Positive/Negative mode Mass analyzer Identification level
Mazzone et al. 2016 LC ESI negative linear ion-trap MS/MS
Roś-Mazurczyk et al. 2017 GC – – TOF In-source fragmentation
Callejón-Leblic et al. 2019 DI ESI negative Q-TOF MS/MS
Mu et al. 2019 GC – – – –
Huang et al. 2019 LC ESI negative Q-Orbitrap MS/MS
Moreno et al. 2018 LC, GC ESI, EI positive, negative LC: linear ion‐trap, GC: single‐quadrupole LC: MS/MS
Moreno et al. 2018 LC, GC ESI, EI positive, negative LC: linear ion‐trap, GC: single‐quadrupole LC: MS/MS
Reference Data processing software Database search
Mazzone et al. 2016 Metabolon LIMS system Metabolon LIMS system
Roś-Mazurczyk et al. 2017 Leco ChromaTOF-GC Replib, Mainlib and Fiehn libraries
Callejón-Leblic et al. 2019 – HMDB, Metlin
Mu et al. 2019 – –
Huang et al. 2019 XCMS OSI-SMMS
Moreno et al. 2018 – KEGG, HMDB
Moreno et al. 2018 – KEGG, HMDB
Reference Difference method Mean concentration (case) Mean concentration (control) Fold change (case/control) P-value FDR VIP
Mazzone et al. 2016 two- sample independent t test 1.165736± 0.5301326 1.185746± 0.78978 0.98312454775306 0.8242501 0.767842753 –
Roś-Mazurczyk et al. 2017 two-sample T test, U Mann-Whitney test, Benjamini-Hochberg approach 1.1822 ± 1.6287 1.1189 ± 0.87031 1.05657342032353 0.5771 0.76992 –
Callejón-Leblic et al. 2019 PCA, PLS-DA, one-way ANOVA – – 0.72 0.03 – 1.43
Mu et al. 2019 PCA, PLS-DA, Mann-Whitney U test – – 0.789 0.003 0.008 1.079
Huang et al. 2019 OPLS-DA, Mann-Whitney U test – – 0.57646401 0.000273125 – 1.6699338
Moreno et al. 2018 paired two‐sample t‐test, PLS-DA – – 1.85918952196766 0.0000000720024225909396 0.000000986996328892148 –
Moreno et al. 2018 paired two‐sample t‐test, PLS-DA – – 2.17878299459397 0.000000000000560284408066284 0.00000000000745178262728158 –
Reference Classification method Cutoff value AUROC 95%CI Sensitivity (%) Specificity (%) Accuracy (%)
Mazzone et al. 2016 – – – – – –
Roś-Mazurczyk et al. 2017 ROC curve – – – – –
Callejón-Leblic et al. 2019 ROC curve – 0.65 – – –
Mu et al. 2019 – – – – – –
Huang et al. 2019 – – – – – –
Moreno et al. 2018 – – – – – –
Moreno et al. 2018 – – – – – –