MiMeDB: Showing metabocard for Forphenicine (MMDBc0001840)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-14 20:22:27 UTC

Update Date

2025-10-07 16:04:31 UTC

Metabolite ID

MMDBc0001840

Metabolite Identification

Common Name

Forphenicine

Description

Forphenicine is a microbial metabolite belonging to the class of alkaline phosphatase inhibitors, first discovered by Umezawa. It has been shown that a derivative containing forphenicine exhibited the broadest dose-response range when administered intraperitoneally (PMID:2753818 ). Analytical methods have been developed for the high-performance liquid chromatographic determination of forphenicine in biological samples, specifically in mouse serum and muscle, utilizing pre-column fluorescence derivatization with 1,2-diamino-4,5-ethylenedioxybenzene as a fluorogenic reagent (PMID:3235509 ). This method allows quantification of forphenicine in small sample volumes, highlighting its distribution after oral administration (PMID:3235509 ). Additionally, forphenicine has been associated with enhanced immune responses, as evidenced by its binding to cells alongside other compounds like bestatin and arphamenine (PMID:3842696 ). Forphenicinol, a low molecular immunomodifier derived from forphenicine, has also been identified, although literature on this metabolite remains limited (PMID:3978657 ). Overall, forphenicine's role in immunomodulation and its pharmacokinetics in biological systems underscore its potential significance in biomedical research.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004271515272D          

 14 14  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 N   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
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   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
    0.7145   -0.4125    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   -1.6500    0.0000 O   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
   -0.7145   -0.4125    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  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
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  6 14  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0001840

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO4/c10-8(9(13)14)5-1-2-6(4-11)7(12)3-5/h1-4,8,12H,10H2,(H,13,14)

> <INCHI_KEY>
MWSKDGPKFCWPOF-UHFFFAOYSA-N

> <FORMULA>
C9H9NO4

> <MOLECULAR_WEIGHT>
195.174

> <EXACT_MASS>
195.053157774

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
18.35837478042832

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-2-(4-formyl-3-hydroxyphenyl)acetic acid

> <ALOGPS_LOGP>
-2.02

> <JCHEM_LOGP>
-1.4138630844745945

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.515844956418757

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3169054000209082

> <JCHEM_PKA_STRONGEST_BASIC>
7.7419578245033325

> <JCHEM_POLAR_SURFACE_AREA>
100.62000000000002

> <JCHEM_REFRACTIVITY>
48.92620000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
amino(4-formyl-3-hydroxyphenyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-15         0                                  
HETATM    1  N   UNK     0       2.667   4.620   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    6                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

Synonyms

Value	Source
2-Amino-2-(4-formyl-3-hydroxyphenyl)acetate	Generator
4-Formyl-3-hydroxyphenylglycine	MeSH
Forfenicin	MeSH

Molecular Formula

C₉H₉NO₄

Average Mass

195.174

Monoisotopic Mass

195.053157774

IUPAC Name

2-amino-2-(4-formyl-3-hydroxyphenyl)acetic acid

Traditional Name

amino(4-formyl-3-hydroxyphenyl)acetic acid

CAS Registry Number

Not Available

SMILES

NC(C(O)=O)C1=CC=C(C=O)C(O)=C1

InChI Identifier

InChI=1S/C9H9NO4/c10-8(9(13)14)5-1-2-6(4-11)7(12)3-5/h1-4,8,12H,10H2,(H,13,14)

InChI Key

MWSKDGPKFCWPOF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Hydroxybenzaldehyde
Benzaldehyde
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Aryl-aldehyde
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Aldehyde
Organooxygen compound
Organonitrogen compound
Primary amine
Primary aliphatic amine
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Organic nitrogen 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	2.34 g/L	ALOGPS
logP	-2	ALOGPS
logP	-1.4	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	7.74	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.62 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.93 m³·mol⁻¹	ChemAxon
Polarizability	18.36 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	455.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	257.0
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	48.7
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	303.2
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	279.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	301.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	700.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	797.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	633.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	160.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	425.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	175.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	78.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	389.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	559.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	57.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	232.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	829.4
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	646.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Forphenicine_TMS_1	C[Si](C)(C)OC(=O)C(N)C1=CC=C(C=O)C(O)=C1	standard non polar	2025-10-23	1919.98
Gas Chromatography	Forphenicine_TMS_2	C[Si](C)(C)OC1=CC(C(N)C(=O)O)=CC=C1C=O	standard non polar	2025-10-23	2164.65
Gas Chromatography	Forphenicine_TMS_3	C[Si](C)(C)NC(C(=O)O)C1=CC=C(C=O)C(O)=C1	standard non polar	2025-10-23	1917.02
Gas Chromatography	Forphenicine_TMS_4	C[Si](C)(C)OC(=O)C(N)C1=CC=C(C=O)C(O[Si](C)(C)C)=C1	standard non polar	2025-10-23	2257.36
Gas Chromatography	Forphenicine_TMS_5	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1=CC=C(C=O)C(O)=C1	standard non polar	2025-10-23	2212.94
Gas Chromatography	Forphenicine_TMS_6	C[Si](C)(C)NC(C(=O)O)C1=CC=C(C=O)C(O[Si](C)(C)C)=C1	standard non polar	2025-10-23	1540.48
Gas Chromatography	Forphenicine_TMS_7	C[Si](C)(C)N(C(C(=O)O)C1=CC=C(C=O)C(O)=C1)[Si](C)(C)C	standard non polar	2025-10-23	1678.1
Gas Chromatography	Forphenicine_TMS_8	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1=CC=C(C=O)C(O[Si](C)(C)C)=C1	standard non polar	2025-10-23	1800.09
Gas Chromatography	Forphenicine_TMS_9	C[Si](C)(C)OC(=O)C(C1=CC=C(C=O)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1878.24
Gas Chromatography	Forphenicine_TMS_10	C[Si](C)(C)OC1=CC(C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1C=O	standard non polar	2025-10-23	2411.5
Gas Chromatography	Forphenicine_TMS_11	C[Si](C)(C)OC(=O)C(C1=CC=C(C=O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1920.0
Gas Chromatography	Forphenicine_TMS_1	C[Si](C)(C)OC(=O)C(N)C1=CC=C(C=O)C(O)=C1	standard polar	2025-10-23	2223.86
Gas Chromatography	Forphenicine_TMS_2	C[Si](C)(C)OC1=CC(C(N)C(=O)O)=CC=C1C=O	standard polar	2025-10-23	2252.07
Gas Chromatography	Forphenicine_TMS_3	C[Si](C)(C)NC(C(=O)O)C1=CC=C(C=O)C(O)=C1	standard polar	2025-10-23	2002.89
Gas Chromatography	Forphenicine_TMS_4	C[Si](C)(C)OC(=O)C(N)C1=CC=C(C=O)C(O[Si](C)(C)C)=C1	standard polar	2025-10-23	2043.09
Gas Chromatography	Forphenicine_TMS_5	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1=CC=C(C=O)C(O)=C1	standard polar	2025-10-23	1549.91
Gas Chromatography	Forphenicine_TMS_6	C[Si](C)(C)NC(C(=O)O)C1=CC=C(C=O)C(O[Si](C)(C)C)=C1	standard polar	2025-10-23	2524.41
Gas Chromatography	Forphenicine_TMS_7	C[Si](C)(C)N(C(C(=O)O)C1=CC=C(C=O)C(O)=C1)[Si](C)(C)C	standard polar	2025-10-23	1718.49
Gas Chromatography	Forphenicine_TMS_8	C[Si](C)(C)NC(C(=O)O[Si](C)(C)C)C1=CC=C(C=O)C(O[Si](C)(C)C)=C1	standard polar	2025-10-23	2266.84
Gas Chromatography	Forphenicine_TMS_9	C[Si](C)(C)OC(=O)C(C1=CC=C(C=O)C(O)=C1)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2173.0
Gas Chromatography	Forphenicine_TMS_10	C[Si](C)(C)OC1=CC(C(C(=O)O)N([Si](C)(C)C)[Si](C)(C)C)=CC=C1C=O	standard polar	2025-10-23	2118.7
Gas Chromatography	Forphenicine_TMS_11	C[Si](C)(C)OC(=O)C(C1=CC=C(C=O)C(O[Si](C)(C)C)=C1)N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	3106.21

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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	Actinobacteria	2	Human ; Human feces; Human saliva; Human urine; Human supragingival plaque; Human sputum; Human subgingival plaque	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

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

42560

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Forphenicine (MMDBc0001840)

MOL for #<Metabolite:0x00007f2e00c2cbc8>

3D MOL for #<Metabolite:0x00007f2e00c2cbc8>

3D SDF for #<Metabolite:0x00007f2e00c2cbc8>

3D-SDF for #<Metabolite:0x00007f2e00c2cbc8>

PDB for #<Metabolite:0x00007f2e00c2cbc8>

3D PDB for #<Metabolite:0x00007f2e00c2cbc8>

SMILES for #<Metabolite:0x00007f2e00c2cbc8>

INCHI for #<Metabolite:0x00007f2e00c2cbc8>

Structure for #<Metabolite:0x00007f2e00c2cbc8>

3D Structure for #<Metabolite:0x00007f2e00c2cbc8>