MiMeDB: Showing metabocard for Pyrophen (MMDBc0007043)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 00:22:27 UTC

Update Date

2025-10-07 16:05:16 UTC

Metabolite ID

MMDBc0007043

Metabolite Identification

Common Name

Pyrophen

Description

Pyrophen is a secondary metabolite belonging to the chemical class of amino acid-pyrone derivatives. It has garnered attention in biomedical research due to its notable biological activities, particularly its antifungal and anticancer properties. Studies have demonstrated that pyrophen exhibits antifungal activity against various strains, with minimum inhibitory concentration (MIC) values ranging from 4.37 to 280.61 µg/mL (PMID:39770520 ). Additionally, pyrophen has been isolated from the endophytic fungus Aspergillus fumigatus strain KARSV04, where it was shown to synergize the effects of doxorubicin in MCF7 breast cancer cells, although it did not significantly enhance doxorubicin-induced cytotoxicity in T47D cells (PMID:32636705 ). Furthermore, pyrophen has been implicated in modulating the cell cycle, particularly inducing a slight increase in the S-phase cell population in T47D cells (PMID:32636705 ). The synthesis of pyrophen complexes with actinides has also been reported, indicating its potential utility in coordination chemistry (PMID:39435794 ). Overall, pyrophen represents a compound of interest for its multifaceted roles in both antifungal activity and cancer research.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152102222D          

 22 23  0  0  1  0            999 V2000
   -1.4289    3.3000    0.0000 C   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
   -1.4289   -1.6500    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
   -2.1434   -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
   -2.1434   -0.4125    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
    0.0000   -0.0000    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    2.4750    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  1  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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
 11  1  1  4  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14  8  1  0  0  0  0
 15  9  2  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  2  0  0  0  0
 14 17  1  1  0  0  0
 18 11  1  0  0  0  0
 19 16  2  0  0  0  0
 20  2  1  0  0  0  0
 20 13  1  0  0  0  0
 21 15  1  0  0  0  0
 21 16  1  0  0  0  0
 14 22  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0007043

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](CC1=CC=CC=C1)(N=C(C)O)C1=CC(OC)=CC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C16H17NO4/c1-11(18)17-14(8-12-6-4-3-5-7-12)15-9-13(20-2)10-16(19)21-15/h3-7,9-10,14H,8H2,1-2H3,(H,17,18)/t14-/m0/s1

> <INCHI_KEY>
VFMQMACUYWGDOJ-AWEZNQCLSA-N

> <FORMULA>
C16H17NO4

> <MOLECULAR_WEIGHT>
287.315

> <EXACT_MASS>
287.115758031

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.74669978604043

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(1S)-1-(4-methoxy-2-oxo-2H-pyran-6-yl)-2-phenylethyl]ethanimidic acid

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
2.2194693979999993

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.405697245925452

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.022803290187941

> <JCHEM_PKA_STRONGEST_BASIC>
2.6961175179574557

> <JCHEM_POLAR_SURFACE_AREA>
68.12

> <JCHEM_REFRACTIVITY>
80.7626

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.92e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1S)-1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   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  N   UNK     0      -1.334   3.850   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
CONECT    1   11                                                            
CONECT    2   20                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   12                                                       
CONECT    7    5   12                                                       
CONECT    8   12   14                                                       
CONECT    9   13   15                                                       
CONECT   10   13   16                                                       
CONECT   11    1   17   18                                                  
CONECT   12    6    7    8                                                  
CONECT   13    9   10   20                                                  
CONECT   14    8   15   17   22                                             
CONECT   15    9   14   21                                                  
CONECT   16   10   19   21                                                  
CONECT   17   11   14                                                       
CONECT   18   11                                                            
CONECT   19   16                                                            
CONECT   20    2   13                                                       
CONECT   21   15   16                                                       
CONECT   22   14                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

Synonyms

Value	Source
4-Methoxy-6-(1'-acetamido-2'-phenylethyl)-2H-pyran-2-one	MeSH

Molecular Formula

C₁₆H₁₇NO₄

Average Mass

287.315

Monoisotopic Mass

287.115758031

IUPAC Name

N-[(1S)-1-(4-methoxy-2-oxo-2H-pyran-6-yl)-2-phenylethyl]ethanimidic acid

Traditional Name

N-[(1S)-1-(4-methoxy-6-oxopyran-2-yl)-2-phenylethyl]ethanimidic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](CC1=CC=CC=C1)(N=C(C)O)C1=CC(OC)=CC(=O)O1

InChI Identifier

InChI=1S/C16H17NO4/c1-11(18)17-14(8-12-6-4-3-5-7-12)15-9-13(20-2)10-16(19)21-15/h3-7,9-10,14H,8H2,1-2H3,(H,17,18)/t14-/m0/s1

InChI Key

VFMQMACUYWGDOJ-AWEZNQCLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kavalactones. These are lactones, which is structurally characterized by a benzene ring and a pyranone moiety, linked to each other to form a 4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Kavalactones

Sub Class

Not Available

Direct Parent

Kavalactones

Alternative Parents

Substituents

Kavalactone
Amphetamine or derivatives
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Acetamide
Vinylogous ester
Carboxamide group
Lactone
Secondary carboxylic acid amide
Carboxylic acid derivative
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Carbonyl group
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.039 g/L	ALOGPS
logP	2.57	ALOGPS
logP	2.22	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	6.02	ChemAxon
pKa (Strongest Basic)	2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.12 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	80.76 m³·mol⁻¹	ChemAxon
Polarizability	29.75 Å³	ChemAxon
Number of Rings	2	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 (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

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	193.5
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	31.5
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	391.3
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	350.7
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	378.1
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	250.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1373.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	107.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	308.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	296.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	271.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	175.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	150.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	10.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	297.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	91.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	248.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1038.3
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	880.5

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Pyrophen_TMS_1	COC1=CC(=O)OC([C@H](CC2=CC=CC=C2)N=C(C)O[Si](C)(C)C)=C1	standard non polar	2025-10-23	2074.33
Gas Chromatography	Pyrophen_TMS_1	COC1=CC(=O)OC([C@H](CC2=CC=CC=C2)N=C(C)O[Si](C)(C)C)=C1	standard polar	2025-10-23	2225.4

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
Eukaryota/Fungi	Ascomycota	1	Human feces	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

C00046868

Chemspider ID

116112

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131349

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

VFMQMACUYWGDOJ-AWEZNQCLSA-N

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 Pyrophen (MMDBc0007043)

MOL for #<Metabolite:0x00007f2e2e4eba48>

3D MOL for #<Metabolite:0x00007f2e2e4eba48>

3D SDF for #<Metabolite:0x00007f2e2e4eba48>

3D-SDF for #<Metabolite:0x00007f2e2e4eba48>

PDB for #<Metabolite:0x00007f2e2e4eba48>

3D PDB for #<Metabolite:0x00007f2e2e4eba48>

SMILES for #<Metabolite:0x00007f2e2e4eba48>

INCHI for #<Metabolite:0x00007f2e2e4eba48>

Structure for #<Metabolite:0x00007f2e2e4eba48>

3D Structure for #<Metabolite:0x00007f2e2e4eba48>