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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2017-03-23 03:54:50 UTC
Update Date2022-09-22 18:34:29 UTC
HMDB IDHMDB0062549
Secondary Accession Numbers
  • HMDB62549
Metabolite Identification
Common Name2-Hydroxystearic acid
Description2-Hydroxystearic acid (CAS: 629-22-1), also known as 2-hydroxystearate or 2-hydroxyoctadecanoic 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-hydroxystearic acid bears a hydroxyl group. 2-Hydroxystearic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 2-Hydroxystearic acid can be found in feces. 2-Hydroxystearic acid can be synthesized from octadecanoic acid, and can be synthesized into 2-hydroxystearoyl-CoA and N-2-hydroxystearoylsphingosine.
Structure
Data?1571842585
Synonyms
ValueSource
(S)-2-Hydroxystearic acidChEBI
(S)-2-HydroxystearateGenerator
(S)-2-HydroxyoctadecanoateGenerator
(-)-alpha-HydroxystearateHMDB
(-)-alpha-Hydroxystearic acidHMDB
(-)-α-HydroxystearateHMDB
(-)-α-Hydroxystearic acidHMDB
(2S)-2-HydroxyoctadecanoateHMDB
(2S)-2-Hydroxyoctadecanoic acidHMDB
(S)-2-Hydroxyoctadecanoic acidHMDB
(±)-alpha-HydroxystearateHMDB
(±)-alpha-Hydroxystearic acidHMDB
(±)-α-HydroxystearateHMDB
(±)-α-Hydroxystearic acidHMDB
2-HydroxyoctadecanoateHMDB
2-Hydroxyoctadecanoic acidHMDB
2-HydroxystearateHMDB
2-Hydroxystearic acidHMDB
DL-2-HydroxystearateHMDB
DL-2-Hydroxystearic acidHMDB
FA(18:0(2-OH))HMDB
FA(18:0(2S-OH))HMDB
L-(-)-2-HydroxystearateHMDB
L-(-)-2-Hydroxystearic acidHMDB
L-2-HydroxyoctadecanoateHMDB
L-2-Hydroxyoctadecanoic acidHMDB
L-2-HydroxystearateHMDB
L-2-Hydroxystearic acidHMDB
alpha-HydroxyoctadecanoateHMDB
alpha-Hydroxyoctadecanoic acidHMDB
alpha-HydroxystearateHMDB
alpha-Hydroxystearic acidHMDB
α-HydroxyoctadecanoateHMDB
α-Hydroxyoctadecanoic acidHMDB
α-HydroxystearateHMDB
α-Hydroxystearic acidHMDB
Chemical FormulaC18H36O3
Average Molecular Weight300.483
Monoisotopic Molecular Weight300.266445019
IUPAC Name(2S)-2-hydroxyoctadecanoic acid
Traditional Name(S)-2-hydroxystearic acid
CAS Registry Number26531-80-6
SMILES
CCCCCCCCCCCCCCCC[C@H](O)C(O)=O
InChI Identifier
InChI=1S/C18H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17(19)18(20)21/h17,19H,2-16H2,1H3,(H,20,21)/t17-/m0/s1
InChI KeyKIHBGTRZFAVZRV-KRWDZBQOSA-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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00094 g/lALOGPS
LogP7.07ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP7.07ALOGPS
logP6.27ChemAxon
logS-5.5ALOGPS
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 Count16ChemAxon
Refractivity87.78 m³·mol⁻¹ChemAxon
Polarizability39.42 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
DeepCCS[M+H]+180.21130932474
DeepCCS[M-H]-176.75930932474
DeepCCS[M-2H]-212.61730932474
DeepCCS[M+Na]+188.90730932474
AllCCS[M+H]+186.432859911
AllCCS[M+H-H2O]+183.532859911
AllCCS[M+NH4]+189.032859911
AllCCS[M+Na]+189.832859911
AllCCS[M-H]-180.432859911
AllCCS[M+Na-2H]-181.532859911
AllCCS[M+HCOO]-182.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Hydroxystearic acidCCCCCCCCCCCCCCCC[C@H](O)C(O)=O3368.6Standard polar33892256
2-Hydroxystearic acidCCCCCCCCCCCCCCCC[C@H](O)C(O)=O2259.7Standard non polar33892256
2-Hydroxystearic acidCCCCCCCCCCCCCCCC[C@H](O)C(O)=O2340.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Hydroxystearic acid,1TMS,isomer #1CCCCCCCCCCCCCCCC[C@H](O[Si](C)(C)C)C(=O)O2406.7Semi standard non polar33892256
2-Hydroxystearic acid,1TMS,isomer #2CCCCCCCCCCCCCCCC[C@H](O)C(=O)O[Si](C)(C)C2332.3Semi standard non polar33892256
2-Hydroxystearic acid,2TMS,isomer #1CCCCCCCCCCCCCCCC[C@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C2430.2Semi standard non polar33892256
2-Hydroxystearic acid,1TBDMS,isomer #1CCCCCCCCCCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)C(=O)O2653.8Semi standard non polar33892256
2-Hydroxystearic acid,1TBDMS,isomer #2CCCCCCCCCCCCCCCC[C@H](O)C(=O)O[Si](C)(C)C(C)(C)C2588.4Semi standard non polar33892256
2-Hydroxystearic acid,2TBDMS,isomer #1CCCCCCCCCCCCCCCC[C@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2914.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Hydroxystearic acid 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 - 2-Hydroxystearic acid 10V, Positive-QTOFsplash10-0udi-3159000000-7975a8415bd8e9a924192021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxystearic acid 20V, Positive-QTOFsplash10-0a59-9531000000-fcb4708799e4d197140b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxystearic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-dae9b4648f722bf578392021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxystearic acid 10V, Negative-QTOFsplash10-0002-0090000000-f0b5fb24866d41ab9f4a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxystearic acid 20V, Negative-QTOFsplash10-0002-1090000000-a10cc6e0109e8cc0e5532021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Hydroxystearic acid 40V, Negative-QTOFsplash10-0006-9000000000-cadfbfc1bbb9a8dfed442021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation 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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC03045
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439887
PDB IDNot Available
ChEBI ID18129
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. 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. 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 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.