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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:17:14 UTC
Update Date2022-03-07 02:54:06 UTC
HMDB IDHMDB0034442
Secondary Accession Numbers
  • HMDB34442
Metabolite Identification
Common NameL-trans-alpha-Amino-2-carboxycyclopropaneacetic acid
DescriptionL-trans-alpha-Amino-2-carboxycyclopropaneacetic 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). L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid has been detected, but not quantified in, fruits. This could make L-trans-alpha-amino-2-carboxycyclopropaneacetic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid.
Structure
Data?1563862564
Synonyms
ValueSource
L-trans-a-Amino-2-carboxycyclopropaneacetateGenerator
L-trans-a-Amino-2-carboxycyclopropaneacetic acidGenerator
L-trans-alpha-Amino-2-carboxycyclopropaneacetateGenerator
L-trans-Α-amino-2-carboxycyclopropaneacetateGenerator
L-trans-Α-amino-2-carboxycyclopropaneacetic acidGenerator
L-CCG-IHMDB, MeSH
L-CCG-IIMeSH, HMDB
(alpha-Carboxycyclopropyl)glycine, (1R-(1alpha(s*),2alpha))-isomerMeSH, HMDB
(alpha-Carboxycyclopropyl)glycine, (1R-(1alpha(s*),2beta))-isomerMeSH, HMDB
3,4-CyclopropylglutamateMeSH, HMDB
L-2-(Carboxypropyl)glycineMeSH, HMDB
alpha-(Carboxycyclopropyl)glycineMeSH, HMDB
(alpha-Carboxycyclopropyl)glycineMeSH, HMDB
(alpha-Carboxycyclopropyl)glycine, (1S-(1alpha(r*),2alpha))-isomerMeSH, HMDB
(alpha-Carboxycyclopropyl)glycine, (1S-(1alpha(r*),2beta))-isomerMeSH, HMDB
2-(Carboxycyclopropyl)glycineMeSH, HMDB
L-CCG IIIMeSH, HMDB
2-[Amino(carboxy)methyl]cyclopropane-1-carboxylateGenerator
CCPGMeSH
Chemical FormulaC6H9NO4
Average Molecular Weight159.14
Monoisotopic Molecular Weight159.053157781
IUPAC Name2-[amino(carboxy)methyl]cyclopropane-1-carboxylic acid
Traditional Name2-[amino(carboxy)methyl]cyclopropane-1-carboxylic acid
CAS Registry Number117857-93-9
SMILES
NC(C1CC1C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H9NO4/c7-4(6(10)11)2-1-3(2)5(8)9/h2-4H,1,7H2,(H,8,9)(H,10,11)
InChI KeyGZOVEPYOCJWRFC-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
  • Cyclopropanecarboxylic acid
  • Cyclopropanecarboxylic acid or derivatives
  • Dicarboxylic acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
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 Solubility82.8 g/LALOGPS
logP-3.5ALOGPS
logP-3.2ChemAxon
logS-0.28ALOGPS
pKa (Strongest Acidic)1.8ChemAxon
pKa (Strongest Basic)9.58ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity33.93 m³·mol⁻¹ChemAxon
Polarizability14.52 ųChemAxon
Number of Rings1ChemAxon
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]+133.19831661259
DarkChem[M-H]-128.31331661259
DeepCCS[M+H]+127.99130932474
DeepCCS[M-H]-124.31530932474
DeepCCS[M-2H]-161.6530932474
DeepCCS[M+Na]+136.76830932474
AllCCS[M+H]+134.332859911
AllCCS[M+H-H2O]+130.132859911
AllCCS[M+NH4]+138.132859911
AllCCS[M+Na]+139.332859911
AllCCS[M-H]-128.732859911
AllCCS[M+Na-2H]-130.032859911
AllCCS[M+HCOO]-131.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acidNC(C1CC1C(O)=O)C(O)=O2248.3Standard polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acidNC(C1CC1C(O)=O)C(O)=O1314.3Standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acidNC(C1CC1C(O)=O)C(O)=O2045.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)C1CC1C(N)C(=O)O1559.7Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C(N)C1CC1C(=O)O1565.9Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,1TMS,isomer #3C[Si](C)(C)NC(C(=O)O)C1CC1C(=O)O1630.5Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C(N)C1CC1C(=O)O[Si](C)(C)C1575.4Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,2TMS,isomer #2C[Si](C)(C)NC(C(=O)O)C1CC1C(=O)O[Si](C)(C)C1664.3Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,2TMS,isomer #3C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1CC1C(=O)O1662.5Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,2TMS,isomer #4C[Si](C)(C)N(C(C(=O)O)C1CC1C(=O)O)[Si](C)(C)C1833.4Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,3TMS,isomer #1C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1CC1C(=O)O[Si](C)(C)C1658.5Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,3TMS,isomer #1C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1CC1C(=O)O[Si](C)(C)C1694.0Standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)C1CC1C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1837.8Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,3TMS,isomer #2C[Si](C)(C)OC(=O)C1CC1C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1744.5Standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,3TMS,isomer #3C[Si](C)(C)OC(=O)C(C1CC1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1811.1Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,3TMS,isomer #3C[Si](C)(C)OC(=O)C(C1CC1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1753.2Standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C1CC1C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1790.3Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,4TMS,isomer #1C[Si](C)(C)OC(=O)C1CC1C(C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1824.8Standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1CC1C(N)C(=O)O1819.5Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C(N)C1CC1C(=O)O1821.4Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(C(=O)O)C1CC1C(=O)O1892.6Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C(N)C1CC1C(=O)O[Si](C)(C)C(C)(C)C2009.6Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NC(C(=O)O)C1CC1C(=O)O[Si](C)(C)C(C)(C)C2135.2Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C1CC1C(=O)O2115.9Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N(C(C(=O)O)C1CC1C(=O)O)[Si](C)(C)C(C)(C)C2259.0Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C1CC1C(=O)O[Si](C)(C)C(C)(C)C2282.0Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)NC(C(=O)O[Si](C)(C)C(C)(C)C)C1CC1C(=O)O[Si](C)(C)C(C)(C)C2303.1Standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1CC1C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2483.2Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C1CC1C(C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2351.2Standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(C1CC1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2472.9Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C(C1CC1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2367.1Standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1CC1C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2656.5Semi standard non polar33892256
L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C1CC1C(C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2583.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-01vo-9200000000-e4d4e2f531562b6c68942017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid GC-MS (2 TMS) - 70eV, Positivesplash10-000i-5910000000-bea7ed5375bb776431db2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - L-trans-alpha-Amino-2-carboxycyclopropaneacetic 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 - L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid 10V, Positive-QTOFsplash10-03di-3900000000-576334df064ead9d4b9e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid 20V, Positive-QTOFsplash10-03xs-9500000000-f04e9ec316ed4a67e9552015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid 40V, Positive-QTOFsplash10-014r-9000000000-c6ad56d0702bcc7bd73a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid 10V, Negative-QTOFsplash10-0bt9-1900000000-c8d6ae7f8a0d370c31c02015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid 20V, Negative-QTOFsplash10-08mi-8900000000-b9eebda15bd751ae323b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid 40V, Negative-QTOFsplash10-00du-9100000000-bc5e955f03f86c90e29a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid 10V, Negative-QTOFsplash10-06r2-5900000000-fa3643f80b3c80057dbb2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid 20V, Negative-QTOFsplash10-01ot-9700000000-fffedc5377b18df1bc5e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid 40V, Negative-QTOFsplash10-0006-9000000000-636fb8a0b726698fb76f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid 10V, Positive-QTOFsplash10-03xs-9700000000-c2c7679ad75ba9e940882021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid 20V, Positive-QTOFsplash10-014j-9000000000-31aa9dd51d7ed72e4b432021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - L-trans-alpha-Amino-2-carboxycyclopropaneacetic acid 40V, Positive-QTOFsplash10-014i-9000000000-3b9f37911a668ca0bf322021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012849
KNApSAcK IDC00054453
Chemspider ID1233
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1271
PDB IDNot Available
ChEBI ID173420
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .