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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:40:43 UTC
Update Date2020-02-26 16:25:51 UTC
HMDB IDHMDB0031057
Secondary Accession Numbers
  • HMDB0062548
  • HMDB31057
  • HMDB62548
Metabolite Identification
Common Name2-Hydroxyhexadecanoic acid
Description2-Hydroxyhexadecanoic acid (CAS: 764-67-0), also known as 2-hydroxypalmitic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. The chain of 2-hydroxyhexadecanoic acid bears a hydroxyl group. 2-Hydroxyhexadecanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 2-Hydroxyhexadecanoic acid occurs in wool fat, which is used as a chewing gum softener.
Structure
Data?1571842137
Synonyms
ValueSource
2S-HydroxypalmitateGenerator
(2S)-2-HydroxyhexadecanoateHMDB
(2S)-2-Hydroxyhexadecanoic acidHMDB
(S)-2-HydroxyhexadecanoateHMDB
(S)-2-Hydroxyhexadecanoic acidHMDB
(S)-2-HydroxypalmitateHMDB
(S)-2-Hydroxypalmitic acidHMDB
(S)-alpha-HydroxypalmitateHMDB
(S)-alpha-Hydroxypalmitic acidHMDB
(S)-α-HydroxypalmitateHMDB
(S)-α-Hydroxypalmitic acidHMDB
(±)-2-HydroxyhexadecanoateHMDB
(±)-2-Hydroxyhexadecanoic acidHMDB
(±)-alpha-HydroxypalmitateHMDB
(±)-alpha-Hydroxypalmitic acidHMDB
(±)-α-HydroxypalmitateHMDB
(±)-α-Hydroxypalmitic acidHMDB
2-HydroxyhexadecanoateHMDB
2-Hydroxyhexadecanoic acidHMDB
2-HydroxypalmitateHMDB
2-Hydroxypalmitic acidHMDB
DL-2-HydroxyhexadecanoateHMDB
DL-2-Hydroxyhexadecanoic acidHMDB
DL-2-HydroxypalmitateHMDB
DL-2-Hydroxypalmitic acidHMDB
FA(16:0(2-OH))HMDB
FA(16:0(2S-OH))HMDB
L-2-HydroxyhexadecanoateHMDB
L-2-Hydroxyhexadecanoic acidHMDB
L-2-HydroxypalmitateHMDB
L-2-Hydroxypalmitic acidHMDB
alpha-HydroxyhexadecanoateHMDB
alpha-Hydroxyhexadecanoic acidHMDB
alpha-HydroxypalmitateHMDB
alpha-Hydroxypalmitic acidHMDB
α-HydroxyhexadecanoateHMDB
α-Hydroxyhexadecanoic acidHMDB
α-HydroxypalmitateHMDB
α-Hydroxypalmitic acidHMDB
Chemical FormulaC16H32O3
Average Molecular Weight272.429
Monoisotopic Molecular Weight272.23514489
IUPAC Name(2S)-2-hydroxyhexadecanoic acid
Traditional Name(2S)-2-hydroxyhexadecanoic acid
CAS Registry Number16452-52-1
SMILES
CCCCCCCCCCCCCC[C@H](O)C(O)=O
InChI Identifier
InChI=1S/C16H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15(17)16(18)19/h15,17H,2-14H2,1H3,(H,18,19)/t15-/m0/s1
InChI KeyJGHSBPIZNUXPLA-HNNXBMFYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point93.3 - 93.6 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0039 g/LALOGPS
logP5.55ALOGPS
logP5.39ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)4.26ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity78.58 m³·mol⁻¹ChemAxon
Polarizability35.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1920000000-b6822f7cbd56cfd6a839Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12575964
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Jones JM, Morrell JC, Gould SJ: Identification and characterization of HAOX1, HAOX2, and HAOX3, three human peroxisomal 2-hydroxy acid oxidases. J Biol Chem. 2000 Apr 28;275(17):12590-7. [PubMed:10777549 ]
  6. 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 ]
  7. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.