MiMeDB: Showing metabocard for 4-hydroxy-3-[(2E,6E)-farnesyl]-6-(pyridin-3-yl)-2H-pyran-2-one (MMDBc0055484)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:54:31 UTC

Update Date

2022-08-12 20:09:23 UTC

Metabolite ID

MMDBc0055484

Metabolite Identification

Common Name

4-hydroxy-3-[(2E,6E)-farnesyl]-6-(pyridin-3-yl)-2H-pyran-2-one

Description

CHEBI:149708 belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review very few articles have been published on CHEBI:149708.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221542D          

 31 32  0  0  0  0            999 V2000
   -5.7158   12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    8.2500    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
   -5.0013   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 C   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
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    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    3.7125    0.0000 C   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
   -5.0013   11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    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    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   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
   -2.1434    4.5375    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
   -0.0000    4.9500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 O   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
   -4.2868    8.2500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  5  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 14 13  1  0  0  0  0
 15  7  1  0  0  0  0
 18  1  1  0  0  0  0
 18  2  1  0  0  0  0
 18  8  2  0  0  0  0
 19  3  1  0  0  0  0
 19  9  1  0  0  0  0
 19 10  2  0  0  0  0
 20  4  1  0  0  0  0
 20 11  1  0  0  0  0
 20 13  2  0  0  0  0
 21 12  1  0  0  0  0
 21 17  2  0  0  0  0
 22 14  1  0  0  0  0
 23 16  1  0  0  0  0
 23 22  2  0  0  0  0
 24 16  2  0  0  0  0
 24 21  1  0  0  0  0
 25 22  1  0  0  0  0
 26 15  2  0  0  0  0
 26 17  1  0  0  0  0
 27 23  1  0  0  0  0
 28 25  2  0  0  0  0
 29 24  1  0  0  0  0
 29 25  1  0  0  0  0
 30 10  1  0  0  0  0
 31 13  1  0  0  0  0
M  CHG  1  27  -1
M  END


  Mrv1652306172221542D          

 31 32  0  0  0  0            999 V2000
   -5.7158   12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   12.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   10.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    8.2500    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
   -5.0013   11.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 C   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
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    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    3.7125    0.0000 C   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
   -5.0013   11.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    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    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   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
   -2.1434    4.5375    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
   -0.0000    4.9500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 O   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
   -4.2868    8.2500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  5  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 14 13  1  0  0  0  0
 15  7  1  0  0  0  0
 18  1  1  0  0  0  0
 18  2  1  0  0  0  0
 18  8  2  0  0  0  0
 19  3  1  0  0  0  0
 19  9  1  0  0  0  0
 19 10  2  0  0  0  0
 20  4  1  0  0  0  0
 20 11  1  0  0  0  0
 20 13  2  0  0  0  0
 21 12  1  0  0  0  0
 21 17  2  0  0  0  0
 22 14  1  0  0  0  0
 23 16  1  0  0  0  0
 23 22  2  0  0  0  0
 24 16  2  0  0  0  0
 24 21  1  0  0  0  0
 25 22  1  0  0  0  0
 26 15  2  0  0  0  0
 26 17  1  0  0  0  0
 27 23  1  0  0  0  0
 28 25  2  0  0  0  0
 29 24  1  0  0  0  0
 29 25  1  0  0  0  0
 30 10  1  0  0  0  0
 31 13  1  0  0  0  0
M  CHG  1  27  -1
M  END
> <DATABASE_ID>
MMDBc0055484

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CC\C(C)=C(/[H])CC1=C([O-])C=C(OC1=O)C1=CN=CC=C1)=C(\C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H31NO3/c1-18(2)8-5-9-19(3)10-6-11-20(4)13-14-22-23(27)16-24(29-25(22)28)21-12-7-15-26-17-21/h7-8,10,12-13,15-17,27H,5-6,9,11,14H2,1-4H3/p-1/b19-10+,20-13+

> <INCHI_KEY>
ZNJZUQFWKYQGPY-OPBVARBZSA-M

> <FORMULA>
C25H30NO3

> <MOLECULAR_WEIGHT>
392.52

> <EXACT_MASS>
392.22311741

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
45.437890946056974

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-oxo-6-(pyridin-3-yl)-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-2H-pyran-4-olate

> <JCHEM_LOGP>
5.3573657013333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.13951576366688

> <JCHEM_PKA_STRONGEST_BASIC>
4.2055129542834875

> <JCHEM_POLAR_SURFACE_AREA>
62.25

> <JCHEM_REFRACTIVITY>
133.22820000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-oxo-6-(pyridin-3-yl)-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]pyran-4-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0     -10.669  23.100   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.002  23.100   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335  18.480   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002  20.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  15.400   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.336  20.790   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -8.002  18.480   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.668  16.170   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  13.860   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.336  22.330   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.668  17.710   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      -4.001   2.310   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0      -0.000   9.240   0.000  0.00  0.00           O-1
HETATM   28  O   UNK     0      -5.335   9.240   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   30  H   UNK     0      -8.002  15.400   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0      -5.335  10.780   0.000  0.00  0.00           H+0
CONECT    1   18                                                            
CONECT    2   18                                                            
CONECT    3   19                                                            
CONECT    4   20                                                            
CONECT    5    8    9                                                       
CONECT    6   10   11                                                       
CONECT    7   12   15                                                       
CONECT    8    5   18                                                       
CONECT    9    5   19                                                       
CONECT   10    6   19   30                                                  
CONECT   11    6   20                                                       
CONECT   12    7   21                                                       
CONECT   13   14   20   31                                                  
CONECT   14   13   22                                                       
CONECT   15    7   26                                                       
CONECT   16   23   24                                                       
CONECT   17   21   26                                                       
CONECT   18    1    2    8                                                  
CONECT   19    3    9   10                                                  
CONECT   20    4   11   13                                                  
CONECT   21   12   17   24                                                  
CONECT   22   14   23   25                                                  
CONECT   23   16   22   27                                                  
CONECT   24   16   21   29                                                  
CONECT   25   22   28   29                                                  
CONECT   26   15   17                                                       
CONECT   27   23                                                            
CONECT   28   25                                                            
CONECT   29   24   25                                                       
CONECT   30   10                                                            
CONECT   31   13                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END

Synonyms

Not Available

Molecular Formula

C₂₅H₃₀NO₃

Average Mass

392.52

Monoisotopic Mass

392.22311741

IUPAC Name

2-oxo-6-(pyridin-3-yl)-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-2H-pyran-4-olate

Traditional Name

2-oxo-6-(pyridin-3-yl)-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]pyran-4-olate

CAS Registry Number

Not Available

SMILES

[H]\C(CC\C(C)=C(/[H])CC1=C([O-])C=C(OC1=O)C1=CN=CC=C1)=C(\C)CCC=C(C)C

InChI Identifier

InChI=1S/C25H31NO3/c1-18(2)8-5-9-19(3)10-6-11-20(4)13-14-22-23(27)16-24(29-25(22)28)21-12-7-15-26-17-21/h7-8,10,12-13,15-17,27H,5-6,9,11,14H2,1-4H3/p-1/b19-10+,20-13+

InChI Key

ZNJZUQFWKYQGPY-OPBVARBZSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Farsesane sesquiterpenoid
Sesquiterpenoid
Pyranone
Pyridine
Pyran
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic anion
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
logP	5.36	ChemAxon
pKa (Strongest Acidic)	7.14	ChemAxon
pKa (Strongest Basic)	4.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	62.25 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	133.23 m³·mol⁻¹	ChemAxon
Polarizability	45.44 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

Spectra

Not Available

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

Metabolic Reactions

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

Exposure Sources

Source Type	Source Sub-type	Species	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

146170871

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 4-hydroxy-3-[(2E,6E)-farnesyl]-6-(pyridin-3-yl)-2H-pyran-2-one (MMDBc0055484)

MOL for #<Metabolite:0x00007fecaafd80b0>

3D MOL for #<Metabolite:0x00007fecaafd80b0>

3D SDF for #<Metabolite:0x00007fecaafd80b0>

3D-SDF for #<Metabolite:0x00007fecaafd80b0>

PDB for #<Metabolite:0x00007fecaafd80b0>

3D PDB for #<Metabolite:0x00007fecaafd80b0>

SMILES for #<Metabolite:0x00007fecaafd80b0>

INCHI for #<Metabolite:0x00007fecaafd80b0>

Structure for #<Metabolite:0x00007fecaafd80b0>

3D Structure for #<Metabolite:0x00007fecaafd80b0>