NP-MRD: Showing NP-Card for 2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid (NP0238544)

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Record Information

Version

2.0

Created at

2022-09-06 21:57:35 UTC

Updated at

2022-09-06 21:57:35 UTC

NP-MRD ID

NP0238544

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid

Description

Phenylalanylleucine 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. 2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid is found in Arabidopsis thaliana. 2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid was first documented in 2020 (PMID: 32060129). Based on a literature review very few articles have been published on Phenylalanylleucine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 42  0  0  0  0  0  0  0  0999 V2000
    4.2079    1.6540   -1.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2949    0.9769   -0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0175    1.7394   -0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2141   -0.4563   -0.5209 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3791   -1.3297    0.3431 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0186   -0.8761    0.3466 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2513   -0.8277   -0.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7391   -1.2395   -1.8958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1295   -0.3500   -0.5700 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0987   -1.3283   -1.0223 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4691   -0.0315    0.8676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8961    0.4456    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1689    1.7683    0.6965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4879    2.1789    0.6917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5133    1.2711    0.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2089   -0.0578    1.0087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8931   -0.4673    1.0135 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3838   -2.7458   -0.1431 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3394   -3.3596   -0.4616 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5997   -3.4299   -0.2531 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7301    2.5227   -0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9013    0.8995   -1.6033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5607    1.9891   -2.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8217    1.1149    0.8333 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5790    1.6811   -1.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2815    2.8186   -0.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3335    1.5060    0.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2682   -0.8606   -0.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9498   -0.5478   -1.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7395   -1.3905    1.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4547   -0.7793   -2.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2473    0.5472   -1.2081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0521   -2.2205   -0.5095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1719   -1.4058   -2.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8135    0.7189    1.3239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4208   -0.9614    1.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3488    2.4772    0.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421    3.2148    0.5665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5641    1.5581    0.8487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0013   -0.7966    1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7175   -1.5397    1.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8795   -4.0803    0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  5 18  1  0
 18 20  1  0
 18 19  2  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  1
  8 31  1  0
  9 32  1  6
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 17 41  1  0
 20 42  1  0
M  END


  Mrv1652309062223572D          

 20 20  0  0  0  0            999 V2000
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 N   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
    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 N   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
    0.7145   -0.4125    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
    0.0000    0.8250    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    0.8250    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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0238544

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H22N2O3/c1-10(2)8-13(15(19)20)17-14(18)12(16)9-11-6-4-3-5-7-11/h3-7,10,12-13H,8-9,16H2,1-2H3,(H,17,18)(H,19,20)

> <INCHI_KEY>
RFCVXVPWSPOMFJ-UHFFFAOYSA-N

> <FORMULA>
C15H22N2O3

> <MOLECULAR_WEIGHT>
278.352

> <EXACT_MASS>
278.163042576

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.537402073352155

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid

> <JCHEM_LOGP>
0.14775236470033337

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
4.480053165979121

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5653437527470433

> <JCHEM_PKA_STRONGEST_BASIC>
9.534679181495314

> <JCHEM_POLAR_SURFACE_AREA>
95.91000000000001

> <JCHEM_REFRACTIVITY>
76.60900000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       1.334  -5.390   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       4.001  -2.310   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18    5   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂N₂O₃

Average Mass

278.3520 Da

Monoisotopic Mass

278.16304 Da

IUPAC Name

2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid

Traditional Name

2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)CC(N=C(O)C(N)CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C15H22N2O3/c1-10(2)8-13(15(19)20)17-14(18)12(16)9-11-6-4-3-5-7-11/h3-7,10,12-13H,8-9,16H2,1-2H3,(H,17,18)(H,19,20)

InChI Key

RFCVXVPWSPOMFJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Arabidopsis thaliana	LOTUS Database	35616633

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
Phenylalanine or derivatives
Leucine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Amphetamine or derivatives
Aralkylamine
Fatty amide
Benzenoid
Monocyclic benzene moiety
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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	0.15	ChemAxon
pKa (Strongest Acidic)	3.57	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.91 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	76.61 m³·mol⁻¹	ChemAxon
Polarizability	30.54 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0253025

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3293068

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

4078229

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Stolzenberg-Solomon R, Derkach A, Moore S, Weinstein SJ, Albanes D, Sampson J: Associations between metabolites and pancreatic cancer risk in a large prospective epidemiological study. Gut. 2020 Nov;69(11):2008-2015. doi: 10.1136/gutjnl-2019-319811. Epub 2020 Feb 14. [PubMed:32060129 ]
LOTUS database [Link]

Showing NP-Card for 2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid (NP0238544)

MOL for NP0238544 (2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid)

3D MOL for NP0238544 (2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid)

3D SDF for NP0238544 (2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid)

3D-SDF for NP0238544 (2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid)

PDB for NP0238544 (2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid)

3D PDB for NP0238544 (2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid)

SMILES for NP0238544 (2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid)

INCHI for NP0238544 (2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid)

Structure for NP0238544 (2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid)

3D Structure for NP0238544 (2-[(2-amino-1-hydroxy-3-phenylpropylidene)amino]-4-methylpentanoic acid)