NP-MRD: Showing NP-Card for Pro-Pro-Phe (NP0340148)

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Record Information

Version

2.0

Created at

2024-09-12 01:45:40 UTC

Updated at

2024-09-12 01:45:40 UTC

NP-MRD ID

NP0340148

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pro-Pro-Phe

Description

Pro-Pro-Phe was first documented in 2019 (PMID: 30604615). Based on a literature review a significant number of articles have been published on Pro-Pro-Phe (PMID: 35806175) (PMID: 38629756) (PMID: 38512162) (PMID: 36240562) (PMID: 35684487) (PMID: 34893975).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05272304172D          

 26 28  0  0  0  0            999 V2000
    5.4568    6.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2853    5.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2415    7.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9661   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3987    1.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8984    5.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8546    6.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7111   -0.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862    2.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7911   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8467    1.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2961    5.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6830    5.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3786    0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1246    4.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1793    2.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5662    2.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3786    1.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3400    4.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0460   -0.1600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7377    3.7419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0930    1.5625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7816    2.6800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6641    1.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1685    3.2321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7269    4.5911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 15 12  1  0  0  0  0
 16  9  1  0  0  0  0
 17 16  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 20 10  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  4  0  0  0
 21 17  2  0  0  0  0
 22 11  1  0  0  0  0
 22 16  1  0  0  0  0
 22 18  1  0  0  0  0
 23 17  1  0  0  0  0
 24 18  2  0  0  0  0
 25 19  2  0  0  0  0
 26 19  1  0  0  0  0
M  END


  Mrv2104 05272304172D          

 26 28  0  0  0  0            999 V2000
    5.4568    6.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2853    5.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2415    7.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9661   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3987    1.8400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8984    5.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8546    6.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7111   -0.1600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862    2.5545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7911   -0.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8467    1.2269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2961    5.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6830    5.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3786    0.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1246    4.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1793    2.3829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5662    2.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3786    1.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3400    4.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0460   -0.1600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7377    3.7419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0930    1.5625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7816    2.6800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6641    1.5625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1685    3.2321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7269    4.5911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 13  6  2  0  0  0  0
 13  7  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 15 12  1  0  0  0  0
 16  9  1  0  0  0  0
 17 16  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 20 10  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  1  4  0  0  0
 21 17  2  0  0  0  0
 22 11  1  0  0  0  0
 22 16  1  0  0  0  0
 22 18  1  0  0  0  0
 23 17  1  0  0  0  0
 24 18  2  0  0  0  0
 25 19  2  0  0  0  0
 26 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0340148

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C(CC1=CC=CC=C1)N=C(O)C1CCCN1C(=O)C1CCCN1

> <INCHI_IDENTIFIER>
InChI=1/C19H25N3O4/c23-17(21-15(19(25)26)12-13-6-2-1-3-7-13)16-9-5-11-22(16)18(24)14-8-4-10-20-14/h1-3,6-7,14-16,20H,4-5,8-12H2,(H,21,23)(H,25,26)

> <INCHI_KEY>
NAIPAPCKKRCMBL-UHFFFAOYNA-N

> <FORMULA>
C19H25N3O4

> <MOLECULAR_WEIGHT>
359.426

> <EXACT_MASS>
359.184506297

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.3953692579141

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-({hydroxy[1-(pyrrolidine-2-carbonyl)pyrrolidin-2-yl]methylidene}amino)-3-phenylpropanoic acid

> <JCHEM_LOGP>
-1.0580094489956715

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.755992175693714

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5579333009232452

> <JCHEM_PKA_STRONGEST_BASIC>
9.817469798245734

> <JCHEM_POLAR_SURFACE_AREA>
102.23

> <JCHEM_REFRACTIVITY>
95.48889999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-({hydroxy[1-(pyrrolidine-2-carbonyl)pyrrolidin-2-yl]methylidene}amino)-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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      10.186  12.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.866  11.107   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.651  13.089   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.003  -1.763   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.544   3.435   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.010  10.076   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.795  12.058   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.527  -0.299   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.774   4.768   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.543  -1.763   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.514   2.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.619   9.522   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.475  10.552   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.773   0.607   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.299   8.015   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      15.268   4.448   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.124   5.479   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.773   2.147   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.835   7.539   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      15.019  -0.299   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0      14.444   6.985   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0      15.107   2.917   0.000  0.00  0.00           N+0
HETATM   23  O   UNK     0      12.659   5.003   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      12.440   2.917   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      11.515   6.033   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      10.690   8.570   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    6                                                       
CONECT    3    1    7                                                       
CONECT    4    8   10                                                       
CONECT    5    9   11                                                       
CONECT    6    2   13                                                       
CONECT    7    3   13                                                       
CONECT    8    4   14                                                       
CONECT    9    5   16                                                       
CONECT   10    4   20                                                       
CONECT   11    5   22                                                       
CONECT   12   13   15                                                       
CONECT   13    6    7   12                                                  
CONECT   14    8   18   20                                                  
CONECT   15   12   19   21                                                  
CONECT   16    9   17   22                                                  
CONECT   17   16   21   23                                                  
CONECT   18   14   22   24                                                  
CONECT   19   15   25   26                                                  
CONECT   20   10   14                                                       
CONECT   21   15   17                                                       
CONECT   22   11   16   18                                                  
CONECT   23   17                                                            
CONECT   24   18                                                            
CONECT   25   19                                                            
CONECT   26   19                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₅N₃O₄

Average Mass

359.4260 Da

Monoisotopic Mass

359.18451 Da

IUPAC Name

2-({hydroxy[1-(pyrrolidine-2-carbonyl)pyrrolidin-2-yl]methylidene}amino)-3-phenylpropanoic acid

Traditional Name

2-({hydroxy[1-(pyrrolidine-2-carbonyl)pyrrolidin-2-yl]methylidene}amino)-3-phenylpropanoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C(CC1=CC=CC=C1)N=C(O)C1CCCN1C(=O)C1CCCN1

InChI Identifier

InChI=1/C19H25N3O4/c23-17(21-15(19(25)26)12-13-6-2-1-3-7-13)16-9-5-11-22(16)18(24)14-8-4-10-20-14/h1-3,6-7,14-16,20H,4-5,8-12H2,(H,21,23)(H,25,26)

InChI Key

NAIPAPCKKRCMBL-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-1.1	ChemAxon
pKa (Strongest Acidic)	3.56	ChemAxon
pKa (Strongest Basic)	9.82	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	102.23 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	95.49 m³·mol⁻¹	ChemAxon
Polarizability	37.4 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bojarska J, Breza M, Remko M, Czyz M, Gajos-Michniewicz A, Zimecki M, Kaczmarek K, Madura ID, Wojciechowski JM, Wolf WM: Structural and Biofunctional Insights into the Cyclo(Pro-Pro-Phe-Phe-) Scaffold from Experimental and In Silico Studies: Melanoma and Beyond. Int J Mol Sci. 2022 Jun 28;23(13):7173. doi: 10.3390/ijms23137173. [PubMed:35806175 ]
Li Y, Takamatsu K, Aota T, Konno H: Synthesis and Structural Revision of the Cyclic Hexapeptide Dimers Antatollamides A and B. Org Lett. 2024 Apr 26;26(16):3375-3379. doi: 10.1021/acs.orglett.4c00808. Epub 2024 Apr 17. [PubMed:38629756 ]
Pu L, Kong X, Xing R, Wang Y, Zhang C, Hua Y, Chen Y, Li X: Identification, rapid screening, docking mechanism and in vitro digestion stability of novel DPP-4 inhibitory peptides from wheat gluten with ginger protease. Food Funct. 2024 Apr 2;15(7):3848-3863. doi: 10.1039/d3fo05423c. [PubMed:38512162 ]
Wang X, Deng Y, Xie P, Liu L, Zhang C, Cheng J, Zhang Y, Liu Y, Huang L, Jiang J: Novel bioactive peptides from ginkgo biloba seed protein and evaluation of their alpha-glucosidase inhibition activity. Food Chem. 2023 Mar 15;404(Pt A):134481. doi: 10.1016/j.foodchem.2022.134481. Epub 2022 Oct 3. [PubMed:36240562 ]
Zaczynska E, Kaczmarek K, Zabrocki J, Artym J, Zimecki M: Antiviral Activity of a Cyclic Pro-Pro-beta(3)-HoPhe-Phe Tetrapeptide against HSV-1 and HAdV-5. Molecules. 2022 May 31;27(11):3552. doi: 10.3390/molecules27113552. [PubMed:35684487 ]
Bao X, Yuan X, Li X, Liu X: Flaxseed-derived peptide, IPPF, inhibits intestinal cholesterol absorption in Caco-2 cells and hepatic cholesterol synthesis in HepG2 cells. J Food Biochem. 2022 Jan;46(1):e14031. doi: 10.1111/jfbc.14031. Epub 2021 Dec 11. [PubMed:34893975 ]
Zhang N, Liu H, Zhou X, Wang W, Fan Y, Liu Y: Taste and stability characteristics of two key umami peptides from pufferfish (Takifugu obscurus). Food Chem. 2022 Mar 1;371:131124. doi: 10.1016/j.foodchem.2021.131124. Epub 2021 Sep 15. [PubMed:34563972 ]
Yi SH, Hong SP: Characteristics of Bacterial Strains with Desirable Flavor Compounds from Korean Traditional Fermented Soybean Paste (Doenjang). Molecules. 2021 Aug 21;26(16):5067. doi: 10.3390/molecules26165067. [PubMed:34443655 ]
Ren Y, Wu H, Chi Y, Deng R, He Q: Structural characterization, erythrocyte protection, and antifatigue effect of antioxidant collagen peptides from tilapia (Oreochromis nilotica L.) skin. Food Funct. 2020 Nov 18;11(11):10149-10160. doi: 10.1039/d0fo01803a. [PubMed:33155595 ]
Zhang N, Ayed C, Wang W, Liu Y: Sensory-Guided Analysis of Key Taste-Active Compounds in Pufferfish (Takifugu obscurus). J Agric Food Chem. 2019 Dec 18;67(50):13809-13816. doi: 10.1021/acs.jafc.8b06047. Epub 2019 Jan 17. [PubMed:30604615 ]

Showing NP-Card for Pro-Pro-Phe (NP0340148)

MOL for NP0340148 (Pro-Pro-Phe)

3D MOL for NP0340148 (Pro-Pro-Phe)

3D SDF for NP0340148 (Pro-Pro-Phe)

3D-SDF for NP0340148 (Pro-Pro-Phe)

PDB for NP0340148 (Pro-Pro-Phe)

3D PDB for NP0340148 (Pro-Pro-Phe)

SMILES for NP0340148 (Pro-Pro-Phe)

INCHI for NP0340148 (Pro-Pro-Phe)

Structure for NP0340148 (Pro-Pro-Phe)

3D Structure for NP0340148 (Pro-Pro-Phe)