MiMeDB: Showing metabocard for N-Formylphenylalanine (MMDBc0000725)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:53:36 UTC

Update Date

2024-04-30 19:33:36 UTC

Metabolite ID

MMDBc0000725

Metabolite Identification

Common Name

N-Formylphenylalanine

Description

N-Formylphenylalanine, also known as OHC-Phe-OH, 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. N-Formylphenylalanine has been identified in the human placenta (PMID: 32033212 ).

Structure

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


  Mrv1652311221917072D          

 14 14  0  0  0  0            999 V2000
10000.7294 9999.9999    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.014610000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7294 9999.1770    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.4421 9998.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.442110000.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.1569 9999.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.442110001.2359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.301710000.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.587310000.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.872710000.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8727 9999.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.5872 9998.7633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.3017 9999.1758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.4416 9997.9390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  1  0  0  0
  1  5  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13  8  1  0  0  0  0
  2  8  1  0  0  0  0
  4 14  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000725

> <DATABASE_NAME>
MIME

> <SMILES>
OC(=O)[C@H](CC1=CC=CC=C1)NC=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H11NO3/c12-7-11-9(10(13)14)6-8-4-2-1-3-5-8/h1-5,7,9H,6H2,(H,11,12)(H,13,14)/t9-/m0/s1

> <INCHI_KEY>
NSTPXGARCQOSAU-VIFPVBQESA-N

> <FORMULA>
C10H11NO3

> <MOLECULAR_WEIGHT>
193.1992

> <EXACT_MASS>
193.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
19.115405308047627

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-formamido-3-phenylpropanoic acid

> <ALOGPS_LOGP>
0.55

> <JCHEM_LOGP>
0.8477629480000001

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.903542048267166

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.94464099625633

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5730346292616728

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
50.069600000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.56e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-formamido-3-phenylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-NOV-19         0                                  
HETATM    1  C   UNK     0    8668.0288666.666   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8666.6948667.436   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0    8668.0288665.130   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0    8669.3598664.359   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8669.3598667.436   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8670.6938666.666   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8669.3598668.974   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8665.3638666.668   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.0308667.438   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.6968666.668   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8662.6968665.128   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8664.0298664.358   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.3638665.128   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8669.3588662.819   0.000  0.00  0.00           O+0
CONECT    1    2    3    5                                                  
CONECT    2    1    8                                                       
CONECT    3    1    4                                                       
CONECT    4    3   14                                                       
CONECT    5    1    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    9   13    2                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14    4                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

Synonyms

Value	Source
(2S)-2-Formamido-3-phenyl-propanoic acid	ChEBI
For-phe	ChEBI
N-Formyl-3-phenyl-L-alanine	ChEBI
N-Formylphenylalanine	ChEBI
OHC-Phe-OH	ChEBI
(2S)-2-Formamido-3-phenyl-propanoate	Generator
(2S)-2-Formamido-3-phenylpropanoic acid	HMDB
(2S)-2-Formamido-3-phenylpropionic acid	HMDB
L-N-Formylphenylalanine	HMDB
N-Formyl-3-phenylalanine	HMDB
N-Formyl-L-phenylalanine	HMDB

Molecular Formula

C₁₀H₁₁NO₃

Average Mass

193.1992

Monoisotopic Mass

193.073893223

IUPAC Name

(2S)-2-formamido-3-phenylpropanoic acid

Traditional Name

(2S)-2-formamido-3-phenylpropanoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)[C@H](CC1=CC=CC=C1)NC=O

InChI Identifier

InChI=1S/C10H11NO3/c12-7-11-9(10(13)14)6-8-4-2-1-3-5-8/h1-5,7,9H,6H2,(H,11,12)(H,13,14)/t9-/m0/s1

InChI Key

NSTPXGARCQOSAU-VIFPVBQESA-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
N-acyl-l-alpha-amino acid
N-formyl-alpha-amino acid
N-formyl-alpha amino acid or derivatives
3-phenylpropanoic-acid
Amphetamine or derivatives
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.76 g/L	ALOGPS
logP	0.55	ALOGPS
logP	0.85	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.4 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	50.07 m³·mol⁻¹	ChemAxon
Polarizability	19.12 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00r7-0900000000-e8d98df4ef212a774733	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-2900000000-348a73126a67e691825a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9400000000-3022f16c8dc4a4ab5697	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1900000000-488274cc870f7ae5c645	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9400000000-8c37b2643e9967ae65b8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6x-9500000000-052924441b9cc81dad72	2021-09-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces
Placenta

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	2	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0240317

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

663938

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

759256

PDB ID

Not Available

ChEBI ID

133534

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for N-Formylphenylalanine (MMDBc0000725)

MOL for #<Metabolite:0x00007fdb13c35ff0>

3D MOL for #<Metabolite:0x00007fdb13c35ff0>

3D SDF for #<Metabolite:0x00007fdb13c35ff0>

3D-SDF for #<Metabolite:0x00007fdb13c35ff0>

PDB for #<Metabolite:0x00007fdb13c35ff0>

3D PDB for #<Metabolite:0x00007fdb13c35ff0>

SMILES for #<Metabolite:0x00007fdb13c35ff0>

INCHI for #<Metabolite:0x00007fdb13c35ff0>

Structure for #<Metabolite:0x00007fdb13c35ff0>

3D Structure for #<Metabolite:0x00007fdb13c35ff0>