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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-06 21:02:08 UTC

Update Date

2021-09-14 15:36:50 UTC

HMDB ID

HMDB0028695

Secondary Accession Numbers

HMDB28695

Metabolite Identification

Common Name

Alanylproline

Description

Alanylproline, 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

      
  Mrv1652304032018422D          

 13 13  0  0  0  0            999 V2000
 2499.6746 2500.4341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9602 2500.8467    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 2498.2354 2500.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9602 2501.6740    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3911 2500.8467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0479 2499.5145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.7644 2499.0998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2501.0479 2500.3418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.6578 2499.5934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 2498.9904 2499.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2453 2498.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0703 2498.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.3252 2499.1085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  6  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 13  6  1  6  0  0  0
  1  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0028695

> <DATABASE_NAME>
hmdb

> <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_KEY>
WPWUFUBLGADILS-WDSKDSINSA-N

> <FORMULA>
C8H14N2O3

> <MOLECULAR_WEIGHT>
186.211

> <EXACT_MASS>
186.100442319

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.66480904082092

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-1-[(2S)-2-aminopropanoyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-1.99

> <JCHEM_LOGP>
-3.107002794240429

> <ALOGPS_LOGS>
0.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.706322612953283

> <JCHEM_PKA_STRONGEST_BASIC>
8.381476455934987

> <JCHEM_POLAR_SURFACE_AREA>
83.63000000000001

> <JCHEM_REFRACTIVITY>
45.48380000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-1-[(2S)-2-aminopropanoyl]pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-APR-20         0                                  
HETATM    1  C   UNK     0    4666.0594667.477   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4664.7264668.247   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4663.3734667.500   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0    4664.7264669.791   0.000  0.00  0.00           N+0
HETATM    5  O   UNK     0    4667.3974668.247   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    4668.6234665.760   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    4669.9604664.986   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    4668.6234667.305   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0    4666.0284665.908   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0    4664.7824665.003   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    4665.2584663.538   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    4666.7984663.538   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    4667.2744665.003   0.000  0.00  0.00           C+0
CONECT    1    2    5    9                                                  
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    1                                                            
CONECT    6    7    8   13                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9   10   13    1                                                  
CONECT   10   11    9                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    9    6                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0028695
HETATM    1  C1  UNL     1       3.254   0.684   0.430  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.135  -0.349   0.643  1.00  0.00           C  
HETATM    3  N1  UNL     1       2.084  -1.287  -0.430  1.00  0.00           N  
HETATM    4  C3  UNL     1       0.845   0.329   0.877  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.760   1.122   1.879  1.00  0.00           O  
HETATM    6  N2  UNL     1      -0.249   0.099   0.016  1.00  0.00           N  
HETATM    7  C4  UNL     1      -0.221  -0.748  -1.155  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.570  -0.429  -1.822  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.434  -0.283  -0.595  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.556   0.687   0.214  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.054   0.616   1.597  1.00  0.00           C  
HETATM   12  O2  UNL     1      -1.510   0.075   2.568  1.00  0.00           O  
HETATM   13  O3  UNL     1      -3.288   1.236   1.833  1.00  0.00           O  
HETATM   14  H1  UNL     1       3.293   0.834  -0.681  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.215   0.250   0.714  1.00  0.00           H  
HETATM   16  H3  UNL     1       3.013   1.636   0.931  1.00  0.00           H  
HETATM   17  H4  UNL     1       2.477  -0.911   1.561  1.00  0.00           H  
HETATM   18  H5  UNL     1       2.064  -2.269  -0.081  1.00  0.00           H  
HETATM   19  H6  UNL     1       2.755  -1.128  -1.196  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.182  -1.816  -0.928  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.533  -0.409  -1.900  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.468   0.569  -2.284  1.00  0.00           H  
HETATM   23  H10 UNL     1      -1.888  -1.219  -2.503  1.00  0.00           H  
HETATM   24  H11 UNL     1      -3.420   0.147  -0.797  1.00  0.00           H  
HETATM   25  H12 UNL     1      -2.457  -1.250  -0.075  1.00  0.00           H  
HETATM   26  H13 UNL     1      -1.630   1.665  -0.261  1.00  0.00           H  
HETATM   27  H14 UNL     1      -3.502   2.150   1.444  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    4   17
CONECT    3   18   19
CONECT    4    5    5    6
CONECT    6    7   10
CONECT    7    8   20   21
CONECT    8    9   22   23
CONECT    9   10   24   25
CONECT   10   11   26
CONECT   11   12   12   13
CONECT   13   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
A-P	ChEBI
AP	ChEBI
L-Ala-L-pro	ChEBI
L-Alanyl-L-proline	HMDB
1-L-Alanyl-L-proline	HMDB
1-L-Alanylproline	HMDB
a-p Dipeptide	HMDB
AP dipeptide	HMDB
Ala-pro	HMDB
Alanine proline dipeptide	HMDB
Alanine-proline dipeptide	HMDB
Alanyl-proline	HMDB
L-alpha-Alanyl-L-proline	HMDB
L-Α-alanyl-L-proline	HMDB
N-Alanylproline	HMDB
N-L-Alanyl-L-proline	HMDB
NSC 97932	HMDB
Alanylproline	ChEBI

Chemical Formula

C₈H₁₄N₂O₃

Average Molecular Weight

186.211

Monoisotopic Molecular Weight

186.100442319

IUPAC Name

(2S)-1-[(2S)-2-aminopropanoyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2S)-1-[(2S)-2-aminopropanoyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

13485-59-1

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 Key

WPWUFUBLGADILS-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

dipeptide (CHEBI:73393 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 22308371)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)

Source

Endogenous

Endogenous (HMDB: HMDB0028695)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-3.11	Extrapolated

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	247 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.1	ChemAxon
logS	0.12	ALOGPS
pKa (Strongest Acidic)	3.71	ChemAxon
pKa (Strongest Basic)	8.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.63 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	45.48 m³·mol⁻¹	ChemAxon
Polarizability	18.66 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	140.156	30932474
DeepCCS	[M-H]-	137.798	30932474
DeepCCS	[M-2H]-	172.903	30932474
DeepCCS	[M+Na]+	147.931	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.57 minutes	32390414
Predicted by Siyang on May 30, 2022	9.1238 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.54 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	326.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	607.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	248.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	74.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	49.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	250.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	249.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	720.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	583.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	50.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	737.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	167.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	173.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	603.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	454.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	294.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alanylproline	C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	2529.8	Standard polar	33892256
Alanylproline	C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	1770.7	Standard non polar	33892256
Alanylproline	C[C@H](N)C(=O)N1CCC[C@H]1C(O)=O	1807.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Alanylproline,1TMS,isomer #1	C[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	1721.5	Semi standard non polar	33892256
Alanylproline,1TMS,isomer #2	C[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	1784.8	Semi standard non polar	33892256
Alanylproline,2TMS,isomer #1	C[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	1810.1	Semi standard non polar	33892256
Alanylproline,2TMS,isomer #1	C[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	1827.7	Standard non polar	33892256
Alanylproline,2TMS,isomer #1	C[C@H](N[Si](C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C	2280.3	Standard polar	33892256
Alanylproline,2TMS,isomer #2	C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1894.5	Semi standard non polar	33892256
Alanylproline,2TMS,isomer #2	C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	1891.0	Standard non polar	33892256
Alanylproline,2TMS,isomer #2	C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2518.7	Standard polar	33892256
Alanylproline,3TMS,isomer #1	C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1954.5	Semi standard non polar	33892256
Alanylproline,3TMS,isomer #1	C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	1954.1	Standard non polar	33892256
Alanylproline,3TMS,isomer #1	C[C@@H](C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2155.4	Standard polar	33892256
Alanylproline,1TBDMS,isomer #1	C[C@H](N)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	1958.3	Semi standard non polar	33892256
Alanylproline,1TBDMS,isomer #2	C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O	2036.7	Semi standard non polar	33892256
Alanylproline,2TBDMS,isomer #1	C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2262.0	Semi standard non polar	33892256
Alanylproline,2TBDMS,isomer #1	C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2247.0	Standard non polar	33892256
Alanylproline,2TBDMS,isomer #1	C[C@H](N[Si](C)(C)C(C)(C)C)C(=O)N1CCC[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2449.4	Standard polar	33892256
Alanylproline,2TBDMS,isomer #2	C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2361.5	Semi standard non polar	33892256
Alanylproline,2TBDMS,isomer #2	C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2339.7	Standard non polar	33892256
Alanylproline,2TBDMS,isomer #2	C[C@@H](C(=O)N1CCC[C@H]1C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2571.6	Standard polar	33892256
Alanylproline,3TBDMS,isomer #1	C[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)C	2591.3	Semi standard non polar	33892256
Alanylproline,3TBDMS,isomer #1	C[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)C	2570.1	Standard non polar	33892256
Alanylproline,3TBDMS,isomer #1	C[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)C	2465.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Alanylproline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alanylproline 10V, Positive-QTOF	splash10-00kr-1900000000-442f203054b348970741	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alanylproline 20V, Positive-QTOF	splash10-0006-9500000000-21a8425dbdf1930dd63b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alanylproline 40V, Positive-QTOF	splash10-01bc-9000000000-954e26d9913512bffd51	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alanylproline 10V, Negative-QTOF	splash10-000l-0900000000-eaa4f52e68e3489332d6	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alanylproline 20V, Negative-QTOF	splash10-01vx-4900000000-7844cc94ffc62bcfb584	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alanylproline 40V, Negative-QTOF	splash10-00di-9200000000-1acf565619899c2e2ed9	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alanylproline 10V, Positive-QTOF	splash10-00kr-1900000000-ca0c5297e1ba566612ea	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alanylproline 20V, Positive-QTOF	splash10-01ba-9600000000-714a52c8600665bd7925	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alanylproline 40V, Positive-QTOF	splash10-00di-9000000000-6de9a7deeaa9ed36fa82	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alanylproline 10V, Negative-QTOF	splash10-000i-0900000000-1684198b36646f30acb4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alanylproline 20V, Negative-QTOF	splash10-03di-5900000000-5406486ec353247ee967	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alanylproline 40V, Negative-QTOF	splash10-03dm-9400000000-cb5b17e5fb7c535c90b6	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces
Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Colorectal cancer

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 ]
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 ]
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

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB098189

KNApSAcK ID

Not Available

Chemspider ID

75359

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

83525

PDB ID

Not Available

ChEBI ID

73393

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]
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 ]

Showing metabocard for Alanylproline (HMDB0028695)

MOL for HMDB0028695 (Alanylproline)

3D MOL for HMDB0028695 (Alanylproline)

3D SDF for HMDB0028695 (Alanylproline)

3D-SDF for HMDB0028695 (Alanylproline)

PDB for HMDB0028695 (Alanylproline)

3D PDB for HMDB0028695 (Alanylproline)

SMILES for HMDB0028695 (Alanylproline)

INCHI for HMDB0028695 (Alanylproline)

Structure for HMDB0028695 (Alanylproline)

3D Structure for HMDB0028695 (Alanylproline)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra