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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:32:42 UTC

Update Date

2022-09-22 18:35:05 UTC

HMDB ID

HMDB0341181

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Fructosyl phenylalanine

Description

N-Fructosyl phenylalanine belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on N-Fructosyl phenylalanine.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309092222102D          

 23 24  0  0  0  0            999 V2000
   -0.6514   -6.0978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7376   -5.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0702   -4.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0702   -3.9674    0.0000 O   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
    0.3789   -2.9588    0.0000 O   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
    1.4289   -2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    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
    3.5724   -2.0625    0.0000 O   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
    1.1994   -4.3799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0244   -4.3799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.0474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -5.8320    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 11 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  5 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
  3 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341181

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1OC(O)(CNC(CC2=CC=CC=C2)C(O)=O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H21NO7/c17-7-11-12(18)13(19)15(22,23-11)8-16-10(14(20)21)6-9-4-2-1-3-5-9/h1-5,10-13,16-19,22H,6-8H2,(H,20,21)

> <INCHI_KEY>
FAVRCIXPIVJIPN-UHFFFAOYSA-N

> <FORMULA>
C15H21NO7

> <MOLECULAR_WEIGHT>
327.333

> <EXACT_MASS>
327.13180202

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
32.038463051795844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-phenyl-2-({[2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl}amino)propanoic acid

> <JCHEM_LOGP>
-3.198849521599371

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.754632963985713

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5990333675025674

> <JCHEM_PKA_STRONGEST_BASIC>
8.66057896220583

> <JCHEM_POLAR_SURFACE_AREA>
139.48000000000002

> <JCHEM_REFRACTIVITY>
77.99040000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-phenyl-2-({[2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl}amino)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  O   UNK     0      -1.216 -11.383   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.377  -9.851   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.131  -8.946   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.131  -7.406   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.707  -5.523   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.667  -4.620   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.668  -3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335  -6.160   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.239  -8.176   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.779  -8.176   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.334  -9.422   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.810 -10.886   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   22                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7   20                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17    9   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    5   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20    3   23                                                  
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₁NO₇

Average Molecular Weight

327.333

Monoisotopic Molecular Weight

327.13180202

IUPAC Name

3-phenyl-2-({[2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl}amino)propanoic acid

Traditional Name

3-phenyl-2-({[2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methyl}amino)propanoic acid

CAS Registry Number

Not Available

SMILES

OCC1OC(O)(CNC(CC2=CC=CC=C2)C(O)=O)C(O)C1O

InChI Identifier

InChI=1S/C15H21NO7/c17-7-11-12(18)13(19)15(22,23-11)8-16-10(14(20)21)6-9-4-2-1-3-5-9/h1-5,10-13,16-19,22H,6-8H2,(H,20,21)

InChI Key

FAVRCIXPIVJIPN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
C-glycosyl compound
Glycosyl compound
3-phenylpropanoic-acid
Alpha-amino acid
Amphetamine or derivatives
Pentose monosaccharide
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxolane
Amino acid
Hemiacetal
Secondary alcohol
Carboxylic acid
Secondary aliphatic amine
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Secondary amine
Polyol
Amine
Organic nitrogen compound
Alcohol
Carbonyl group
Organic oxygen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

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	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-3.2	ChemAxon
pKa (Strongest Acidic)	1.6	ChemAxon
pKa (Strongest Basic)	8.66	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	139.48 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	77.99 m³·mol⁻¹	ChemAxon
Polarizability	32.04 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Retention Times

Not Available

Predicted Kovats Retention Indices

Not Available

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

85152457

PDB ID

Not Available

ChEBI ID

Not Available

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

Neto FC, Raftery D: Expanding Urinary Metabolite Annotation through Integrated Mass Spectral Similarity Networking. Anal Chem. 2021 Sep 7;93(35):12001-12010. doi: 10.1021/acs.analchem.1c02041. Epub 2021 Aug 26. [PubMed:34436864 ]

Showing metabocard for N-Fructosyl phenylalanine (HMDB0341181)

MOL for HMDB0341181 (N-Fructosyl phenylalanine)

3D MOL for HMDB0341181 (N-Fructosyl phenylalanine)

3D SDF for HMDB0341181 (N-Fructosyl phenylalanine)

3D-SDF for HMDB0341181 (N-Fructosyl phenylalanine)

PDB for HMDB0341181 (N-Fructosyl phenylalanine)

3D PDB for HMDB0341181 (N-Fructosyl phenylalanine)

SMILES for HMDB0341181 (N-Fructosyl phenylalanine)

INCHI for HMDB0341181 (N-Fructosyl phenylalanine)

Structure for HMDB0341181 (N-Fructosyl phenylalanine)

3D Structure for HMDB0341181 (N-Fructosyl phenylalanine)

Predicted Retention Times

Predicted Kovats Retention Indices