Hmdb loader
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:30 UTC
Update Date2022-03-07 02:49:12 UTC
HMDB IDHMDB0001976
Secondary Accession Numbers
  • HMDB0060113
  • HMDB01976
  • HMDB60113
Metabolite Identification
Common NameDocosapentaenoic acid (22n-6)
DescriptionDocosapentaenoic acid is an unsaturated fatty acid found in fish oils. It is a minor constituent of the total serum unsaturated fatty acids in humans. Docosapentaenoic acid (22n-6) is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Docosapentaenoic acid (22n-6) can be found in blood and urine, as well as in human adipose tissue, fibroblasts, and platelet tissues. Within the cell, docosapentaenoic acid (22n-6) is primarily located in the membrane (predicted from logP). It can also be found in the extracellular space. In humans, docosapentaenoic acid (22n-6) is involved in alpha-linolenic acid and linoleic acid metabolism. Docosapentaenoic acid (22n-6) is found to be associated with thyroid cancer.
Structure
Data?1582752221
Synonyms
ValueSource
(all-Z)-4,7,10,13,16-Docosapentaenoic acidChEBI
22:5(4Z,7Z,10Z,13Z,16Z)ChEBI
4Z,7Z,10Z,13Z,16Z-Docosapentaenoic acidChEBI
all-cis-Docosa-4,7,10,13,16-pentaenoic acidChEBI
DPAn-6ChEBI
(all-Z)-4,7,10,13,16-DocosapentaenoateGenerator
4Z,7Z,10Z,13Z,16Z-DocosapentaenoateGenerator
all-cis-Docosa-4,7,10,13,16-pentaenoateGenerator
Docosapentaenoate (22N-6)Generator
Docosa-4,7,10,13,16-pentaenoic acidHMDB
DocosapentaenoateHMDB
Docosapentaenoic acidHMDB
Osbond acidHMDB
FA(22:5(4Z,7Z,10Z,13Z,16Z))HMDB
(all-Z)-7, 10, 13, 16, 19-Docosapentaenoic acidHMDB
Docosapentaenoic acid (C22:5 N6)HMDB
Docosapentaenoic acid, (all Z)-isomerHMDB
Docosa-4,7,10,13,16-pentaenoic acid, (all-Z)-isomerHMDB
(4Z,7Z,10Z,13Z,16Z)-4,7,10,13,16-Docosapentaenoic acidHMDB
DPAHMDB
FA(22:5n6)HMDB
Chemical FormulaC22H34O2
Average Molecular Weight330.5042
Monoisotopic Molecular Weight330.255880332
IUPAC Name(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoic acid
Traditional Name(4Z,7Z,10Z,13Z,16Z)-docosa-4,7,10,13,16-pentaenoic acid
CAS Registry Number25448-00-4
SMILES
CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O
InChI Identifier
InChI=1S/C22H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10,12-13,15-16,18-19H,2-5,8,11,14,17,20-21H2,1H3,(H,23,24)/b7-6-,10-9-,13-12-,16-15-,19-18-
InChI KeyAVKOENOBFIYBSA-WMPRHZDHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative Parents
Substituents
  • Very long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0001 g/LALOGPS
logP7.18ALOGPS
logP7.11ChemAxon
logS-6.5ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity110.27 m³·mol⁻¹ChemAxon
Polarizability40.58 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+195.24731661259
DarkChem[M-H]-194.72131661259
AllCCS[M+H]+190.07532859911
AllCCS[M-H]-189.01132859911
DeepCCS[M+H]+194.19430932474
DeepCCS[M-H]-191.83630932474
DeepCCS[M-2H]-224.72230932474
DeepCCS[M+Na]+200.28730932474
AllCCS[M+H]+190.132859911
AllCCS[M+H-H2O]+187.232859911
AllCCS[M+NH4]+192.732859911
AllCCS[M+Na]+193.432859911
AllCCS[M-H]-189.032859911
AllCCS[M+Na-2H]-191.032859911
AllCCS[M+HCOO]-193.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Docosapentaenoic acid (22n-6)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O3962.9Standard polar33892256
Docosapentaenoic acid (22n-6)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O2272.3Standard non polar33892256
Docosapentaenoic acid (22n-6)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O2510.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Docosapentaenoic acid (22n-6),1TMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C2560.5Semi standard non polar33892256
Docosapentaenoic acid (22n-6),1TBDMS,isomer #1CCCCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O[Si](C)(C)C(C)(C)C2808.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Docosapentaenoic acid (22n-6) GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fu-7490000000-97ad3e356a5f908f90032017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Docosapentaenoic acid (22n-6) GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9244000000-8e631b61a994e509b1142017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Docosapentaenoic acid (22n-6) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 10V, Positive-QTOFsplash10-01q9-0139000000-31a18234c1c393f0a6a72016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 20V, Positive-QTOFsplash10-0239-4592000000-fa33f23033ae64b975602016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 40V, Positive-QTOFsplash10-006x-7960000000-ccf21f4fdb0af5b5c6192016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 10V, Negative-QTOFsplash10-004i-0019000000-fa512c1688ce00ffd41d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 20V, Negative-QTOFsplash10-004r-1059000000-8f65bcb90bc078a7912d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 40V, Negative-QTOFsplash10-0a4l-9140000000-4ded7c8842575d2752c52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 10V, Negative-QTOFsplash10-004i-0009000000-f4bd181f9378195136602021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 20V, Negative-QTOFsplash10-01t9-1019000000-a6b85cd3220846053c5c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 40V, Negative-QTOFsplash10-052f-9041000000-f6b90f282a7eccd547fd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 10V, Positive-QTOFsplash10-01q9-1239000000-b1d4cd921a69d9f8653f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 20V, Positive-QTOFsplash10-01q9-6933000000-1d63fd3f377179dddb822021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Docosapentaenoic acid (22n-6) 40V, Positive-QTOFsplash10-053u-9800000000-eeb640c3008512e3c40a2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Adipose Tissue
  • Fibroblasts
  • Placenta
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified10.0 +/- 4.1 uMAdult (>18 years old)Not Specified
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified6.4 +/- 5.6 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified13.9 +/- 5.2 uMAdult (>18 years old)Not Specified
Isovaleric acidemia
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
details
UrineDetected and Quantified3.0 +/- 2.3 umol/mmol creatinineAdult (>18 years old)Both
Thyroid cancer
details
Associated Disorders and Diseases
Disease References
Isovaleric acidemia
  1. Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Thyroid cancer
  1. Kim KM, Jung BH, Lho DS, Chung WY, Paeng KJ, Chung BC: Alteration of urinary profiles of endogenous steroids and polyunsaturated fatty acids in thyroid cancer. Cancer Lett. 2003 Dec 30;202(2):173-9. [PubMed:14643447 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022774
KNApSAcK IDNot Available
Chemspider ID4945614
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6412
PubChem Compound6441454
PDB IDNot Available
ChEBI ID65136
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Williard DE, Nwankwo JO, Kaduce TL, Harmon SD, Irons M, Moser HW, Raymond GV, Spector AA: Identification of a fatty acid delta6-desaturase deficiency in human skin fibroblasts. J Lipid Res. 2001 Apr;42(4):501-8. [PubMed:11290821 ]
  2. Marckmann P, Lassen A, Haraldsdottir J, Sandstrom B: Biomarkers of habitual fish intake in adipose tissue. Am J Clin Nutr. 1995 Nov;62(5):956-9. [PubMed:7572741 ]
  3. Pedersen JI, Ringstad J, Almendingen K, Haugen TS, Stensvold I, Thelle DS: Adipose tissue fatty acids and risk of myocardial infarction--a case-control study. Eur J Clin Nutr. 2000 Aug;54(8):618-25. [PubMed:10951510 ]
  4. Park Y, Harris W: EPA, but not DHA, decreases mean platelet volume in normal subjects. Lipids. 2002 Oct;37(10):941-6. [PubMed:12530552 ]
  5. Francois CA, Connor SL, Bolewicz LC, Connor WE: Supplementing lactating women with flaxseed oil does not increase docosahexaenoic acid in their milk. Am J Clin Nutr. 2003 Jan;77(1):226-33. [PubMed:12499346 ]
  6. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  7. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]