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Showing NP-Card for Ala-Phe-Ala (NP0340129)

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Record Information
Version2.0
Created at2024-09-12 01:39:54 UTC
Updated at2024-09-12 01:39:54 UTC
NP-MRD IDNP0340129
Secondary Accession NumbersNone
Natural Product Identification
Common NameAla-Phe-Ala
Description Ala-Phe-Ala was first documented in 2007 (PMID: 17553454). Based on a literature review a significant number of articles have been published on Ala-Phe-Ala (PMID: 33181423) (PMID: 33928264) (PMID: 23999680) (PMID: 18173254) (PMID: 17530827).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0340129 (Ala-Phe-Ala)


  Mrv2104 05272304122D          

 22 22  0  0  0  0            999 V2000
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  4  0  0  0
 17 14  2  0  0  0  0
 18 12  1  4  0  0  0
 18 13  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  2  0  0  0  0
 22 15  1  0  0  0  0
M  END
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3D MOL for NP0340129 (Ala-Phe-Ala)

Download
3D SDF for NP0340129 (Ala-Phe-Ala)

  Mrv2104 05272304122D          

 22 22  0  0  0  0            999 V2000
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  4  0  0  0
 17 14  2  0  0  0  0
 18 12  1  4  0  0  0
 18 13  2  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  2  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0340129

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(N)C(O)=NC(CC1=CC=CC=C1)C(O)=NC(C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C15H21N3O4/c1-9(16)13(19)18-12(8-11-6-4-3-5-7-11)14(20)17-10(2)15(21)22/h3-7,9-10,12H,8,16H2,1-2H3,(H,17,20)(H,18,19)(H,21,22)

> <INCHI_KEY>
XRUJOVRWNMBAAA-UHFFFAOYNA-N

> <FORMULA>
C15H21N3O4

> <MOLECULAR_WEIGHT>
307.35

> <EXACT_MASS>
307.153206168

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
31.76289611487544

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-({2-[(2-amino-1-hydroxypropylidene)amino]-1-hydroxy-3-phenylpropylidene}amino)propanoic acid

> <JCHEM_LOGP>
-1.0158136132236208

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.962518210641252

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.329482006447691

> <JCHEM_PKA_STRONGEST_BASIC>
9.569632605247163

> <JCHEM_POLAR_SURFACE_AREA>
128.5

> <JCHEM_REFRACTIVITY>
80.75450000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-({2-[(2-amino-1-hydroxypropylidene)amino]-1-hydroxy-3-phenylpropylidene}amino)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0340129 (Ala-Phe-Ala)
Download
PDB for NP0340129 (Ala-Phe-Ala)
HEADER    PROTEIN                                 27-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-23         0                                  
HETATM    1  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0       6.668   2.310   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       4.001   6.930   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       4.001   3.850   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335  10.780   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8   11   12                                                       
CONECT    9    1   13   16                                                  
CONECT   10    2   15   17                                                  
CONECT   11    6    7    8                                                  
CONECT   12    8   14   18                                                  
CONECT   13    9   18   19                                                  
CONECT   14   12   17   20                                                  
CONECT   15   10   21   22                                                  
CONECT   16    9                                                            
CONECT   17   10   14                                                       
CONECT   18   12   13                                                       
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22   15                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

Download
3D PDB for NP0340129 (Ala-Phe-Ala)
Download
SMILES for NP0340129 (Ala-Phe-Ala)
CC(N)C(O)=NC(CC1=CC=CC=C1)C(O)=NC(C)C(O)=O
Download
INCHI for NP0340129 (Ala-Phe-Ala)
InChI=1/C15H21N3O4/c1-9(16)13(19)18-12(8-11-6-4-3-5-7-11)14(20)17-10(2)15(21)22/h3-7,9-10,12H,8,16H2,1-2H3,(H,17,20)(H,18,19)(H,21,22)
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H21N3O4
Average Mass307.3500 Da
Monoisotopic Mass307.15321 Da
IUPAC Name2-({2-[(2-amino-1-hydroxypropylidene)amino]-1-hydroxy-3-phenylpropylidene}amino)propanoic acid
Traditional Name2-({2-[(2-amino-1-hydroxypropylidene)amino]-1-hydroxy-3-phenylpropylidene}amino)propanoic acid
CAS Registry NumberNot Available
SMILES
CC(N)C(O)=NC(CC1=CC=CC=C1)C(O)=NC(C)C(O)=O
InChI Identifier
InChI=1/C15H21N3O4/c1-9(16)13(19)18-12(8-11-6-4-3-5-7-11)14(20)17-10(2)15(21)22/h3-7,9-10,12H,8,16H2,1-2H3,(H,17,20)(H,18,19)(H,21,22)
InChI KeyXRUJOVRWNMBAAA-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1ChemAxon
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)9.57ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area128.5 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity80.75 m³·mol⁻¹ChemAxon
Polarizability31.76 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Hernandez B, Pfluger F, Kruglik SG, Ghomi M: Multiconformational analysis of tripeptides upon consideration of implicit and explicit hydration effects. J Mol Graph Model. 2021 Jan;102:107790. doi: 10.1016/j.jmgm.2020.107790. Epub  2020 Oct 30. [PubMed:33181423  ] 
  2. Bera S, Dong X, Krishnarjuna B, Raab SA, Hales DA, Ji W, Tang Y, Shimon LJW, Ramamoorthy A, Clemmer DE, Wei G, Gazit E: Solid-state packing dictates the unexpected solubility of aromatic peptides. Cell Rep Phys Sci. 2021 Apr 21;2(4):100391. doi: 10.1016/j.xcrp.2021.100391. [PubMed:33928264  ] 
  3. Jaeqx S, Oomens J, Rijs AM: Gas-phase salt bridge interactions between glutamic acid and arginine. Phys Chem Chem Phys. 2013 Oct 14;15(38):16341-52. doi: 10.1039/c3cp52508b. Epub  2013 Sep 3. [PubMed:23999680  ] 
  4. Pizzanelli S, Forte C, Monti S, Schweitzer-Stenner R: Interaction of a tripeptide with cesium perfluorooctanoate micelles. J Phys Chem B. 2008 Jan 31;112(4):1251-61. doi: 10.1021/jp073947x. Epub 2008 Jan  4. [PubMed:18173254  ] 
  5. Elston C, Wallach J, Saulnier J: New continuous and specific fluorometric assays for Pseudomonas aeruginosa elastase and LasA protease. Anal Biochem. 2007 Sep 1;368(1):87-94. doi: 10.1016/j.ab.2007.04.041. Epub 2007  May 3. [PubMed:17553454  ] 
  6. Brenner V, Piuzzi F, Dimicoli I, Tardivel B, Mons M: Spectroscopic evidence for the formation of helical structures in gas-phase short peptide chains. J Phys Chem A. 2007 Aug 9;111(31):7347-54. doi: 10.1021/jp070681l. Epub 2007 May  27. [PubMed:17530827  ]