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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 15:47:11 UTC
HMDB IDHMDB0000991
Secondary Accession Numbers
  • HMDB00991
Metabolite Identification
Common NameDL-2-Aminooctanoic acid
DescriptionDL-2-Aminooctanoic acid, also known as a-aminocaprylate or alpha-aminocaprylic acid, belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). DL-2-Aminooctanoic acid has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and milk (cow). This could make DL-2-aminooctanoic acid a potential biomarker for the consumption of these foods. DL-2-Aminooctanoic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a small amount of articles have been published on DL-2-Aminooctanoic acid.
Structure
Data?1582752169
Synonyms
ValueSource
(+-)-2-Aminooctanoic acidChEBI
(+/-)-2-aminooctanoic acidChEBI
2-Amino-DL-caprylic acidChEBI
2-Aminocaprylic acidChEBI
alpha-Aminocaprylic acidChEBI
alpha-Aminooctanoic acidChEBI
D,L-2-Aminooctanoic acidChEBI
DL-2-Aminocaprylic acidChEBI
DL-alpha-Amino-N-caprylic acidChEBI
DL-alpha-Aminocaprylic acidChEBI
NSC 20147ChEBI
(+-)-2-AminooctanoateGenerator
(+/-)-2-aminooctanoateGenerator
2-Amino-DL-caprylateGenerator
2-AminocaprylateGenerator
a-AminocaprylateGenerator
a-Aminocaprylic acidGenerator
alpha-AminocaprylateGenerator
Α-aminocaprylateGenerator
Α-aminocaprylic acidGenerator
a-AminooctanoateGenerator
a-Aminooctanoic acidGenerator
alpha-AminooctanoateGenerator
Α-aminooctanoateGenerator
Α-aminooctanoic acidGenerator
D,L-2-AminooctanoateGenerator
DL-2-AminocaprylateGenerator
DL-a-Amino-N-caprylateGenerator
DL-a-Amino-N-caprylic acidGenerator
DL-alpha-Amino-N-caprylateGenerator
DL-Α-amino-N-caprylateGenerator
DL-Α-amino-N-caprylic acidGenerator
DL-a-AminocaprylateGenerator
DL-a-Aminocaprylic acidGenerator
DL-alpha-AminocaprylateGenerator
DL-Α-aminocaprylateGenerator
DL-Α-aminocaprylic acidGenerator
DL-2-AminooctanoateGenerator
(+/-)-2-amino-octanoateHMDB
(+/-)-2-amino-octanoic acidHMDB
2-Amino-DL-octanoateHMDB
2-Amino-DL-octanoic acidHMDB
2-AminooctanoateHMDB
2-Aminooctanoic acidHMDB
DL-2-Amino-octanoateHMDB
DL-2-Aminooctanoic acidChEBI
Chemical FormulaC8H17NO2
Average Molecular Weight159.2261
Monoisotopic Molecular Weight159.125928793
IUPAC Name2-aminooctanoic acid
Traditional Name(+-)-2-aminooctanoic acid
CAS Registry Number644-90-6
SMILES
CCCCCCC(N)C(O)=O
InChI Identifier
InChI=1S/C8H17NO2/c1-2-3-4-5-6-7(9)8(10)11/h7H,2-6,9H2,1H3,(H,10,11)
InChI KeyAKVBCGQVQXPRLD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acid
  • Fatty acyl
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Adverse health effect

Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point194 - 196 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility19 mg/mLNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg141.62130932474
[M+H]+MetCCS_train_pos147.11930932474
[M-H]-Not Available141.621http://allccs.zhulab.cn/database/detail?ID=AllCCS00000039
[M+H]+Not Available147.227http://allccs.zhulab.cn/database/detail?ID=AllCCS00000039
Predicted Molecular Properties
PropertyValueSource
Water Solubility5.36 g/LALOGPS
logP-0.99ALOGPS
logP-0.54ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)2.89ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity43.43 m³·mol⁻¹ChemAxon
Polarizability18.72 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+137.53331661259
DarkChem[M-H]-134.03131661259
AllCCS[M+H]+139.23332859911
AllCCS[M-H]-136.61132859911
DeepCCS[M+H]+140.48430932474
DeepCCS[M-H]-137.40530932474
DeepCCS[M-2H]-174.4230932474
DeepCCS[M+Na]+149.34430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DL-2-Aminooctanoic acidCCCCCCC(N)C(O)=O2290.6Standard polar33892256
DL-2-Aminooctanoic acidCCCCCCC(N)C(O)=O1343.9Standard non polar33892256
DL-2-Aminooctanoic acidCCCCCCC(N)C(O)=O1395.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
DL-2-Aminooctanoic acid,1TMS,isomer #1CCCCCCC(N)C(=O)O[Si](C)(C)C1385.5Semi standard non polar33892256
DL-2-Aminooctanoic acid,1TMS,isomer #2CCCCCCC(N[Si](C)(C)C)C(=O)O1499.0Semi standard non polar33892256
DL-2-Aminooctanoic acid,2TMS,isomer #1CCCCCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C1512.4Semi standard non polar33892256
DL-2-Aminooctanoic acid,2TMS,isomer #1CCCCCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C1550.5Standard non polar33892256
DL-2-Aminooctanoic acid,2TMS,isomer #1CCCCCCC(N[Si](C)(C)C)C(=O)O[Si](C)(C)C1638.6Standard polar33892256
DL-2-Aminooctanoic acid,2TMS,isomer #2CCCCCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1674.0Semi standard non polar33892256
DL-2-Aminooctanoic acid,2TMS,isomer #2CCCCCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1582.6Standard non polar33892256
DL-2-Aminooctanoic acid,2TMS,isomer #2CCCCCCC(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1830.9Standard polar33892256
DL-2-Aminooctanoic acid,3TMS,isomer #1CCCCCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1738.4Semi standard non polar33892256
DL-2-Aminooctanoic acid,3TMS,isomer #1CCCCCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1674.2Standard non polar33892256
DL-2-Aminooctanoic acid,3TMS,isomer #1CCCCCCC(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1640.2Standard polar33892256
DL-2-Aminooctanoic acid,1TBDMS,isomer #1CCCCCCC(N)C(=O)O[Si](C)(C)C(C)(C)C1604.9Semi standard non polar33892256
DL-2-Aminooctanoic acid,1TBDMS,isomer #2CCCCCCC(N[Si](C)(C)C(C)(C)C)C(=O)O1715.8Semi standard non polar33892256
DL-2-Aminooctanoic acid,2TBDMS,isomer #1CCCCCCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1948.0Semi standard non polar33892256
DL-2-Aminooctanoic acid,2TBDMS,isomer #1CCCCCCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1950.0Standard non polar33892256
DL-2-Aminooctanoic acid,2TBDMS,isomer #1CCCCCCC(N[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1930.9Standard polar33892256
DL-2-Aminooctanoic acid,2TBDMS,isomer #2CCCCCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2080.9Semi standard non polar33892256
DL-2-Aminooctanoic acid,2TBDMS,isomer #2CCCCCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2006.9Standard non polar33892256
DL-2-Aminooctanoic acid,2TBDMS,isomer #2CCCCCCC(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2031.9Standard polar33892256
DL-2-Aminooctanoic acid,3TBDMS,isomer #1CCCCCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2383.1Semi standard non polar33892256
DL-2-Aminooctanoic acid,3TBDMS,isomer #1CCCCCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2257.2Standard non polar33892256
DL-2-Aminooctanoic acid,3TBDMS,isomer #1CCCCCCC(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2033.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - DL-2-Aminooctanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-05fu-9100000000-7d5ac698d9cf144142592017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-2-Aminooctanoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9200000000-7194900e93c55ceecb9c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-2-Aminooctanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-2-Aminooctanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-2-Aminooctanoic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-2-Aminooctanoic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DL-2-Aminooctanoic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-2-Aminooctanoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-03di-2900000000-6f8d1ae24380ba762d8a2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-2-Aminooctanoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0a4i-9200000000-f726c7ea3316749be8662012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-2-Aminooctanoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-052f-9000000000-2758c754fa3d1a8663132012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-2-Aminooctanoic acid 40V, Positive-QTOFsplash10-0006-9000000000-e04294fee2c406beb1122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-2-Aminooctanoic acid 30V, Positive-QTOFsplash10-052f-9000000000-ad48a92512358872fb512021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-2-Aminooctanoic acid 0V, Positive-QTOFsplash10-03di-0900000000-ec2cf9c3603223ab87e62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-2-Aminooctanoic acid 30V, Positive-QTOFsplash10-0a4i-9000000000-1bddc472e708b9a175f62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-2-Aminooctanoic acid 10V, Positive-QTOFsplash10-03di-1900000000-8910bcfa3daf2ec271a42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-2-Aminooctanoic acid 10V, Positive-QTOFsplash10-03di-3900000000-81f63bcc2c24229c72592021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-2-Aminooctanoic acid 10V, Positive-QTOFsplash10-03di-0900000000-e63e2771046ea22cd8bf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-2-Aminooctanoic acid 20V, Positive-QTOFsplash10-08fr-9600000000-c686964935bb4477ec242021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-2-Aminooctanoic acid 0V, Positive-QTOFsplash10-03di-0900000000-b4d4d29022335f41435d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DL-2-Aminooctanoic acid 30V, Positive-QTOFsplash10-06r6-9400000000-f063db799e309f504d292021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-2-Aminooctanoic acid 10V, Positive-QTOFsplash10-03di-0900000000-c66feed5b71a5025efe52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-2-Aminooctanoic acid 20V, Positive-QTOFsplash10-03di-6900000000-f9f0a475bc7498293d962017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-2-Aminooctanoic acid 40V, Positive-QTOFsplash10-052f-9000000000-82eaca67c3b3935627f52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-2-Aminooctanoic acid 10V, Negative-QTOFsplash10-0a4i-0900000000-dc0d56565c9ad5d0f9b12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-2-Aminooctanoic acid 20V, Negative-QTOFsplash10-0a4l-1900000000-6b31a318e752582257c82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-2-Aminooctanoic acid 40V, Negative-QTOFsplash10-0229-9200000000-534c77b8aa02d51ce81a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-2-Aminooctanoic acid 10V, Positive-QTOFsplash10-03di-9600000000-bcc4a413f16a70ae910e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-2-Aminooctanoic acid 20V, Positive-QTOFsplash10-0abc-9000000000-555a29da122e6ad8d3002021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-2-Aminooctanoic acid 40V, Positive-QTOFsplash10-052f-9000000000-9e815841cbada21127362021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-2-Aminooctanoic acid 10V, Negative-QTOFsplash10-0a4i-0900000000-706e735ab28a6583fcd92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-2-Aminooctanoic acid 20V, Negative-QTOFsplash10-0a4i-0900000000-0b28b79e2cbd2e4bdb302021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DL-2-Aminooctanoic acid 40V, Negative-QTOFsplash10-0006-9000000000-b79714cf2e8448b95c852021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder 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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022354
KNApSAcK IDNot Available
Chemspider ID62727
KEGG Compound IDNot Available
BioCyc IDCPD-3687
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5923
PubChem Compound69522
PDB IDNot Available
ChEBI ID75145
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceAbderhalden, E. Specific action of enzymes. A contribution to the question of the possibility of determining by means of enzymes whether amino acids of definite configuration occur in nature and especially as constituents of proteins. Z. physiol. Chem. (1923), 130 205-7.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. PARRY TE: Paper chromatography of 56 amino compounds using phenol and butanol-acetic acid as solvents with illustrative chromatograms of normal and abnormal urines. Clin Chim Acta. 1957 Apr;2(2):115-25. [PubMed:13447222 ]