MiMeDB: Showing metabocard for 2-oxo-3-[(8S)-epoxy-(2E,6E)-farnesyl]-6-(pyridin-3-yl)-2H-pyran-4-olic acid (MMDBc0055272)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:47:55 UTC

Update Date

2022-08-12 20:09:18 UTC

Metabolite ID

MMDBc0055272

Metabolite Identification

Common Name

2-oxo-3-[(8S)-epoxy-(2E,6E)-farnesyl]-6-(pyridin-3-yl)-2H-pyran-4-olic acid

Description

CHEBI:149709 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:149709.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221472D          

 33 35  0  0  1  0            999 V2000
   12.9710   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5421   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6181    1.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3542    1.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5421   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6855   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5421   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8276   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6855   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2565   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1131   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9710   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1131   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9710  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6855   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2565   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2565   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8276   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9710   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9710   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6855   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9710   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3987    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2565   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2565   -9.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3999   -6.1875    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   11.5421   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2565   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1131   -2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5421   -5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9820    0.5834    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 17  1  1  0  0  0  0
 17  7  1  0  0  0  0
 17 10  2  0  0  0  0
 18  2  1  0  0  0  0
 18  8  2  0  0  0  0
 18 11  1  0  0  0  0
 19  9  1  0  0  0  0
 19 16  2  0  0  0  0
 20 12  1  0  0  0  0
 21 15  1  0  0  0  0
 21 20  2  0  0  0  0
 22 15  2  0  0  0  0
 22 19  1  0  0  0  0
 23 13  1  6  0  0  0
 24 20  1  0  0  0  0
 25  3  1  0  0  0  0
 25  4  1  0  0  0  0
 25 23  1  0  0  0  0
 26 14  2  0  0  0  0
 26 16  1  0  0  0  0
 27 21  1  0  0  0  0
 28 24  2  0  0  0  0
 29 22  1  0  0  0  0
 29 24  1  0  0  0  0
 30 23  1  0  0  0  0
 30 25  1  0  0  0  0
 31  8  1  0  0  0  0
 32 10  1  0  0  0  0
 23 33  1  1  0  0  0
M  CHG  1  27  -1
M  END


  Mrv1652306172221472D          

 33 35  0  0  1  0            999 V2000
   12.9710   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5421   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6181    1.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3542    1.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5421   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6855   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5421   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8276   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6855   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2565   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1131   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9710   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1131   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9710  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6855   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2565   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2565   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8276   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9710   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9710   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6855   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9710   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3987    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.2565   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9862    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2565   -9.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3999   -6.1875    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   11.5421   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2565   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1131   -2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5421   -5.3625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9820    0.5834    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  2  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 17  1  1  0  0  0  0
 17  7  1  0  0  0  0
 17 10  2  0  0  0  0
 18  2  1  0  0  0  0
 18  8  2  0  0  0  0
 18 11  1  0  0  0  0
 19  9  1  0  0  0  0
 19 16  2  0  0  0  0
 20 12  1  0  0  0  0
 21 15  1  0  0  0  0
 21 20  2  0  0  0  0
 22 15  2  0  0  0  0
 22 19  1  0  0  0  0
 23 13  1  6  0  0  0
 24 20  1  0  0  0  0
 25  3  1  0  0  0  0
 25  4  1  0  0  0  0
 25 23  1  0  0  0  0
 26 14  2  0  0  0  0
 26 16  1  0  0  0  0
 27 21  1  0  0  0  0
 28 24  2  0  0  0  0
 29 22  1  0  0  0  0
 29 24  1  0  0  0  0
 30 23  1  0  0  0  0
 30 25  1  0  0  0  0
 31  8  1  0  0  0  0
 32 10  1  0  0  0  0
 23 33  1  1  0  0  0
M  CHG  1  27  -1
M  END
> <DATABASE_ID>
MMDBc0055272

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CC\C(C)=C(/[H])CC1=C([O-])C=C(OC1=O)C1=CN=CC=C1)=C(\C)CC[C@]1([H])OC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H31NO4/c1-17(7-5-8-18(2)11-13-23-25(3,4)30-23)10-12-20-21(27)15-22(29-24(20)28)19-9-6-14-26-16-19/h6,8-10,14-16,23,27H,5,7,11-13H2,1-4H3/p-1/b17-10+,18-8+/t23-/m0/s1

> <INCHI_KEY>
RZIYORCRADGFNA-AWVGLTPVSA-M

> <FORMULA>
C25H30NO4

> <MOLECULAR_WEIGHT>
408.519

> <EXACT_MASS>
408.21803203

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
46.634710420122396

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2E,6E)-9-[(2S)-3,3-dimethyloxiran-2-yl]-3,7-dimethylnona-2,6-dien-1-yl]-2-oxo-6-(pyridin-3-yl)-2H-pyran-4-olate

> <JCHEM_LOGP>
4.378630463

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.139515763668767

> <JCHEM_PKA_STRONGEST_BASIC>
4.205512955902854

> <JCHEM_POLAR_SURFACE_AREA>
74.78

> <JCHEM_REFRACTIVITY>
132.06570000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2E,6E)-9-[(2S)-3,3-dimethyloxiran-2-yl]-3,7-dimethylnona-2,6-dien-1-yl]-2-oxo-6-(pyridin-3-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      24.213  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.545  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.954   2.324   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.594   2.324   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.545  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.546 -18.480   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.545  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.212  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.546 -16.940   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.879  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.878  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.213 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.878  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.213 -19.250   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      25.546 -13.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.879 -16.940   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.879  -7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      20.212  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      24.213 -16.170   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.213 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.546 -12.320   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      24.213 -14.630   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.544   0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      22.879 -12.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.774   1.334   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0      22.879 -18.480   0.000  0.00  0.00           N+0
HETATM   27  O   UNK     0      26.880 -11.550   0.000  0.00  0.00           O-1
HETATM   28  O   UNK     0      21.545 -11.550   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      22.879 -13.860   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      16.004   0.000   0.000  0.00  0.00           O+0
HETATM   31  H   UNK     0      18.878  -5.390   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0      21.545 -10.010   0.000  0.00  0.00           H+0
HETATM   33  H   UNK     0      18.633   1.089   0.000  0.00  0.00           H+0
CONECT    1   17                                                            
CONECT    2   18                                                            
CONECT    3   25                                                            
CONECT    4   25                                                            
CONECT    5    7    8                                                       
CONECT    6    9   14                                                       
CONECT    7    5   17                                                       
CONECT    8    5   18   31                                                  
CONECT    9    6   19                                                       
CONECT   10   12   17   32                                                  
CONECT   11   13   18                                                       
CONECT   12   10   20                                                       
CONECT   13   11   23                                                       
CONECT   14    6   26                                                       
CONECT   15   21   22                                                       
CONECT   16   19   26                                                       
CONECT   17    1    7   10                                                  
CONECT   18    2    8   11                                                  
CONECT   19    9   16   22                                                  
CONECT   20   12   21   24                                                  
CONECT   21   15   20   27                                                  
CONECT   22   15   19   29                                                  
CONECT   23   13   25   30   33                                             
CONECT   24   20   28   29                                                  
CONECT   25    3    4   23   30                                             
CONECT   26   14   16                                                       
CONECT   27   21                                                            
CONECT   28   24                                                            
CONECT   29   22   24                                                       
CONECT   30   23   25                                                       
CONECT   31    8                                                            
CONECT   32   10                                                            
CONECT   33   23                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   70    0
END

Synonyms

Not Available

Molecular Formula

C₂₅H₃₀NO₄

Average Mass

408.519

Monoisotopic Mass

408.21803203

IUPAC Name

3-[(2E,6E)-9-[(2S)-3,3-dimethyloxiran-2-yl]-3,7-dimethylnona-2,6-dien-1-yl]-2-oxo-6-(pyridin-3-yl)-2H-pyran-4-olate

Traditional Name

3-[(2E,6E)-9-[(2S)-3,3-dimethyloxiran-2-yl]-3,7-dimethylnona-2,6-dien-1-yl]-2-oxo-6-(pyridin-3-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)CC[C@]1([H])OC1(C)C

InChI Identifier

InChI=1S/C25H31NO4/c1-17(7-5-8-18(2)11-13-23-25(3,4)30-23)10-12-20-21(27)15-22(29-24(20)28)19-9-6-14-26-16-19/h6,8-10,14-16,23,27H,5,7,11-13H2,1-4H3/p-1/b17-10+,18-8+/t23-/m0/s1

InChI Key

RZIYORCRADGFNA-AWVGLTPVSA-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
Monoterpenoid
Monocyclic monoterpenoid
Aromatic monoterpenoid
Pyranone
Pyridine
Pyran
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Azacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
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	4.38	ChemAxon
pKa (Strongest Acidic)	7.14	ChemAxon
pKa (Strongest Basic)	4.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.78 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	132.07 m³·mol⁻¹	ChemAxon
Polarizability	46.63 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

146170857

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 2-oxo-3-[(8S)-epoxy-(2E,6E)-farnesyl]-6-(pyridin-3-yl)-2H-pyran-4-olic acid (MMDBc0055272)

MOL for #<Metabolite:0x00007fecec3e0928>

3D MOL for #<Metabolite:0x00007fecec3e0928>

3D SDF for #<Metabolite:0x00007fecec3e0928>

3D-SDF for #<Metabolite:0x00007fecec3e0928>

PDB for #<Metabolite:0x00007fecec3e0928>

3D PDB for #<Metabolite:0x00007fecec3e0928>

SMILES for #<Metabolite:0x00007fecec3e0928>

INCHI for #<Metabolite:0x00007fecec3e0928>

Structure for #<Metabolite:0x00007fecec3e0928>

3D Structure for #<Metabolite:0x00007fecec3e0928>