Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-06 21:02:08 UTC
Update Date2021-09-14 15:36:50 UTC
HMDB IDHMDB0028695
Secondary Accession Numbers
  • HMDB28695
Metabolite Identification
Common NameAlanylproline
DescriptionAlanylproline, also known as A-P or L-ala-L-pro, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Alanylproline has been detected, but not quantified in, milk (cow). This could make alanylproline a potential biomarker for the consumption of these foods. Alanylproline 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 significant number of articles have been published on Alanylproline.
Structure
Data?1582753327
Synonyms
ValueSource
A-PChEBI
APChEBI
L-Ala-L-proChEBI
L-Alanyl-L-prolineHMDB
1-L-Alanyl-L-prolineHMDB
1-L-AlanylprolineHMDB
a-p DipeptideHMDB
AP dipeptideHMDB
Ala-proHMDB
Alanine proline dipeptideHMDB
Alanine-proline dipeptideHMDB
Alanyl-prolineHMDB
L-alpha-Alanyl-L-prolineHMDB
L-Α-alanyl-L-prolineHMDB
N-AlanylprolineHMDB
N-L-Alanyl-L-prolineHMDB
NSC 97932HMDB
AlanylprolineChEBI
Chemical FormulaC8H14N2O3
Average Molecular Weight186.211
Monoisotopic Molecular Weight186.100442319
IUPAC Name(2S)-1-[(2S)-2-aminopropanoyl]pyrrolidine-2-carboxylic acid
Traditional Name(2S)-1-[(2S)-2-aminopropanoyl]pyrrolidine-2-carboxylic acid
CAS Registry Number13485-59-1
SMILES
C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O
InChI Identifier
InChI=1S/C8H14N2O3/c1-5(9)7(11)10-4-2-3-6(10)8(12)13/h5-6H,2-4,9H2,1H3,(H,12,13)/t5-,6-/m0/s1
InChI KeyWPWUFUBLGADILS-WDSKDSINSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentDipeptides
Alternative Parents
Substituents
  • Alpha-dipeptide
  • Proline or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-l-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Alpha-amino acid or derivatives
  • N-acylpyrrolidine
  • Pyrrolidine carboxylic acid or derivatives
  • Pyrrolidine carboxylic acid
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Amino acid or derivatives
  • Carboxamide group
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
LogP-3.11Extrapolated
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility247 g/LALOGPS
logP-2ALOGPS
logP-3.1ChemAxon
logS0.12ALOGPS
pKa (Strongest Acidic)3.71ChemAxon
pKa (Strongest Basic)8.38ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.63 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.48 m³·mol⁻¹ChemAxon
Polarizability18.66 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
DeepCCS[M+H]+140.15630932474
DeepCCS[M-H]-137.79830932474
DeepCCS[M-2H]-172.90330932474
DeepCCS[M+Na]+147.93130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AlanylprolineC[C@H](N)C(=O)N1CCC[C@H]1C(O)=O2529.8Standard polar33892256
AlanylprolineC[C@H](N)C(=O)N1CCC[C@H]1C(O)=O1770.7Standard non polar33892256
AlanylprolineC[C@H](N)C(=O)N1CCC[C@H]1C(O)=O1807.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Alanylproline,1TMS,isomer #1C[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C1721.5Semi standard non polar33892256
Alanylproline,1TMS,isomer #2C[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O1784.8Semi standard non polar33892256
Alanylproline,2TMS,isomer #1C[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C1810.1Semi standard non polar33892256
Alanylproline,2TMS,isomer #1C[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C1827.7Standard non polar33892256
Alanylproline,2TMS,isomer #1C[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C2280.3Standard polar33892256
Alanylproline,2TMS,isomer #2C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1894.5Semi standard non polar33892256
Alanylproline,2TMS,isomer #2C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C1891.0Standard non polar33892256
Alanylproline,2TMS,isomer #2C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2518.7Standard polar33892256
Alanylproline,3TMS,isomer #1C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1954.5Semi standard non polar33892256
Alanylproline,3TMS,isomer #1C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C1954.1Standard non polar33892256
Alanylproline,3TMS,isomer #1C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C2155.4Standard polar33892256
Alanylproline,1TBDMS,isomer #1C[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C1958.3Semi standard non polar33892256
Alanylproline,1TBDMS,isomer #2C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O2036.7Semi standard non polar33892256
Alanylproline,2TBDMS,isomer #1C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C2262.0Semi standard non polar33892256
Alanylproline,2TBDMS,isomer #1C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C2247.0Standard non polar33892256
Alanylproline,2TBDMS,isomer #1C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C2449.4Standard polar33892256
Alanylproline,2TBDMS,isomer #2C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2361.5Semi standard non polar33892256
Alanylproline,2TBDMS,isomer #2C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2339.7Standard non polar33892256
Alanylproline,2TBDMS,isomer #2C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2571.6Standard polar33892256
Alanylproline,3TBDMS,isomer #1C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2591.3Semi standard non polar33892256
Alanylproline,3TBDMS,isomer #1C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2570.1Standard non polar33892256
Alanylproline,3TBDMS,isomer #1C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2465.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Alanylproline 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 - Alanylproline 10V, Positive-QTOFsplash10-00kr-1900000000-442f203054b3489707412019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylproline 20V, Positive-QTOFsplash10-0006-9500000000-21a8425dbdf1930dd63b2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylproline 40V, Positive-QTOFsplash10-01bc-9000000000-954e26d9913512bffd512019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylproline 10V, Negative-QTOFsplash10-000l-0900000000-eaa4f52e68e3489332d62019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylproline 20V, Negative-QTOFsplash10-01vx-4900000000-7844cc94ffc62bcfb5842019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylproline 40V, Negative-QTOFsplash10-00di-9200000000-1acf565619899c2e2ed92019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylproline 10V, Positive-QTOFsplash10-00kr-1900000000-ca0c5297e1ba566612ea2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylproline 20V, Positive-QTOFsplash10-01ba-9600000000-714a52c8600665bd79252021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylproline 40V, Positive-QTOFsplash10-00di-9000000000-6de9a7deeaa9ed36fa822021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylproline 10V, Negative-QTOFsplash10-000i-0900000000-1684198b36646f30acb42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylproline 20V, Negative-QTOFsplash10-03di-5900000000-5406486ec353247ee9672021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Alanylproline 40V, Negative-QTOFsplash10-03dm-9400000000-cb5b17e5fb7c535c90b62021-10-11Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal 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. 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 ]
  3. 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 IDFDB098189
KNApSAcK IDNot Available
Chemspider ID75359
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound83525
PDB IDNot Available
ChEBI ID73393
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. Ranganathan R, Lu KP, Hunter T, Noel JP: Structural and functional analysis of the mitotic rotamase Pin1 suggests substrate recognition is phosphorylation dependent. Cell. 1997 Jun 13;89(6):875-86. [PubMed:9200606 ]
  2. Goptar' IA, Kulemzina IA, Filippova IIu, Lysogorskaia EN, Oksenoit ES, Zhuzhikov DP, Dunaevskii IaE, Belozerskii MA, Elpidina EN: [Properties of post-proline cleaving enzymes from Tenebrio molitor]. Bioorg Khim. 2008 May-Jun;34(3):310-6. [PubMed:18672677 ]
  3. Daidone I, Iacobucci C, McLain SE, Smith JC: Alteration of water structure by peptide clusters revealed by neutron scattering in the small-angle region (below 1 A(-1)). Biophys J. 2012 Oct 3;103(7):1518-24. doi: 10.1016/j.bpj.2012.08.010. Epub 2012 Oct 2. [PubMed:23062344 ]
  4. Ishikawa H, Matsuda Y, Katayama M, Hara I, Sato H, Kaneko S, Hirakawa S, Matsushima M: Amidolytic activities and prostate-specific antigen in human seminal plasma. Arch Androl. 1999 Sep-Oct;43(2):141-51. [PubMed:10543577 ]
  5. Johnston JA, Jensen M, Lannfelt L, Walker B, Williams CH: Inhibition of prolylendopeptidase does not affect gamma-secretase processing of amyloid precursor protein in a human neuroblastoma cell line. Neurosci Lett. 1999 Dec 17;277(1):33-6. [PubMed:10643891 ]
  6. Sakuma S, Matsumoto T, Yamashita S, Wang Y, Lu ZR: Conjugation of poorly absorptive drugs with mucoadhesive polymers for the improvement of oral absorption of drugs. J Control Release. 2007 Nov 20;123(3):195-202. Epub 2007 Aug 19. [PubMed:17888541 ]
  7. Seymour AA, Asaad MM, Abboa-Offei BE, Smith PL, Rogers WL, Dorso CR: In vivo pharmacology of dual neutral endopeptidase/angiotensin-converting enzyme inhibitors. J Cardiovasc Pharmacol. 1996 Nov;28(5):672-8. [PubMed:8945681 ]
  8. Sugawara M, Toda T, Kobayashi M, Iseki K, Miyazaki K, Shiroto H, Uchino J, Kondo Y: The inhibitory effects of cephalosporin and dipeptide on ceftibuten uptake by human and rat intestinal brush-border membrane vesicles. J Pharm Pharmacol. 1994 Aug;46(8):680-4. [PubMed:7815284 ]
  9. Sasaki Y, Niida A, Tsuji T, Shigenaga A, Fujii N, Otaka A: Stereoselective synthesis of (Z)-alkene-containing proline dipeptide mimetics. J Org Chem. 2006 Jun 23;71(13):4969-79. [PubMed:16776529 ]