MiMeDB: Showing metabocard for Eupenicinicol B (MMDBc0010651)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 02:45:31 UTC

Update Date

2022-08-31 06:32:02 UTC

Metabolite ID

MMDBc0010651

Metabolite Identification

Common Name

Eupenicinicol B

Description

Eupenicinicol B belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'. Based on a literature review very few articles have been published on Eupenicinicol B.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152104452D          

 32 33  0  0  1  0            999 V2000
    2.9899    3.5632    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7077    2.7880    0.0000 C   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
    1.8953    2.6447    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6131    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0197    2.4426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174    2.6297    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7308    3.4532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 H   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
    4.2868   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  6  2  0  0  0  0
 10  9  2  0  0  0  0
 12  3  1  1  0  0  0
 12  7  1  0  0  0  0
 13  4  1  6  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  6  0  0  0
 16 11  1  0  0  0  0
 17  8  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 14  1  0  0  0  0
 19 16  1  0  0  0  0
 20  5  1  1  0  0  0
 20 15  1  0  0  0  0
 20 17  1  6  0  0  0
 20 18  1  0  0  0  0
 16 21  1  1  0  0  0
 22 17  2  0  0  0  0
 19 23  1  1  0  0  0
 24  6  1  0  0  0  0
 25  8  1  0  0  0  0
 12 26  1  6  0  0  0
 13 27  1  1  0  0  0
 14 28  1  1  0  0  0
 15 29  1  1  0  0  0
 16 30  1  6  0  0  0
 18 31  1  6  0  0  0
 19 32  1  6  0  0  0
M  END


  Mrv1652305152104452D          

 32 33  0  0  1  0            999 V2000
    2.9899    3.5632    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6737    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7077    2.7880    0.0000 C   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
    1.8953    2.6447    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6131    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0197    2.4426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5174    2.6297    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7308    3.4532    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 H   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
    4.2868   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  6  2  0  0  0  0
 10  9  2  0  0  0  0
 12  3  1  1  0  0  0
 12  7  1  0  0  0  0
 13  4  1  6  0  0  0
 13 11  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  6  0  0  0
 16 11  1  0  0  0  0
 17  8  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 14  1  0  0  0  0
 19 16  1  0  0  0  0
 20  5  1  1  0  0  0
 20 15  1  0  0  0  0
 20 17  1  6  0  0  0
 20 18  1  0  0  0  0
 16 21  1  1  0  0  0
 22 17  2  0  0  0  0
 19 23  1  1  0  0  0
 24  6  1  0  0  0  0
 25  8  1  0  0  0  0
 12 26  1  6  0  0  0
 13 27  1  1  0  0  0
 14 28  1  1  0  0  0
 15 29  1  1  0  0  0
 16 30  1  6  0  0  0
 18 31  1  6  0  0  0
 19 32  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0010651

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(C)=C(\[H])C(=O)[C@@]1(C)[C@]([H])(C=C[C@@]2([H])[C@]([H])(O)[C@]([H])(O)C[C@@]([H])(C)[C@]12[H])[C@]([H])(C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O3/c1-6-8-17(22)20(5)15(12(3)7-2)10-9-14-18(20)13(4)11-16(21)19(14)23/h6,8-10,12-16,18-19,21,23H,7,11H2,1-5H3/b8-6+/t12-,13-,14-,15-,16-,18+,19+,20-/m1/s1

> <INCHI_KEY>
TYAHOTSECGQFPS-KNJHQLMTSA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.473

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
37.05381561974614

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-[(1S,2S,4aR,5S,6R,8R,8aS)-2-[(2R)-butan-2-yl]-5,6-dihydroxy-1,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]but-2-en-1-one

> <ALOGPS_LOGP>
3.57

> <JCHEM_LOGP>
3.9227785080000004

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.199467533824418

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.714891308940658

> <JCHEM_PKA_STRONGEST_BASIC>
-3.156687083840705

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
95.63459999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.46e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-1-[(1S,2S,4aR,5S,6R,8R,8aS)-2-[(2R)-butan-2-yl]-5,6-dihydroxy-1,8-dimethyl-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]but-2-en-1-one

> <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       5.581   6.651   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.991   3.490   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.054   5.204   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.538   4.937   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   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       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.011   3.490   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.903   4.559   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0       6.566   4.909   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.231   6.446   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       5.335   3.080   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       6.668   0.770   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0       8.002  -1.540   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.001   0.770   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.335  -1.540   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3   12                                                            
CONECT    4   13                                                            
CONECT    5   20                                                            
CONECT    6    1    8   24                                                  
CONECT    7    2   12                                                       
CONECT    8    6   17   25                                                  
CONECT    9   10   14                                                       
CONECT   10    9   15                                                       
CONECT   11   13   16                                                       
CONECT   12    3    7   15   26                                             
CONECT   13    4   11   18   27                                             
CONECT   14    9   18   19   28                                             
CONECT   15   10   12   20   29                                             
CONECT   16   11   19   21   30                                             
CONECT   17    8   20   22                                                  
CONECT   18   13   14   20   31                                             
CONECT   19   14   16   23   32                                             
CONECT   20    5   15   17   18                                             
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23   19                                                            
CONECT   24    6                                                            
CONECT   25    8                                                            
CONECT   26   12                                                            
CONECT   27   13                                                            
CONECT   28   14                                                            
CONECT   29   15                                                            
CONECT   30   16                                                            
CONECT   31   18                                                            
CONECT   32   19                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

Synonyms

Not Available

Molecular Formula

C₂₀H₃₂O₃

Average Mass

320.473

Monoisotopic Mass

320.23514489

IUPAC Name

(2E)-1-[(1S,2S,4aR,5S,6R,8R,8aS)-2-[(2R)-butan-2-yl]-5,6-dihydroxy-1,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]but-2-en-1-one

Traditional Name

(2E)-1-[(1S,2S,4aR,5S,6R,8R,8aS)-2-[(2R)-butan-2-yl]-5,6-dihydroxy-1,8-dimethyl-4a,5,6,7,8,8a-hexahydro-2H-naphthalen-1-yl]but-2-en-1-one

CAS Registry Number

Not Available

SMILES

[H]\C(C)=C(\[H])C(=O)[C@@]1(C)[C@]([H])(C=C[C@@]2([H])[C@]([H])(O)[C@]([H])(O)C[C@@]([H])(C)[C@]12[H])[C@]([H])(C)CC

InChI Identifier

InChI=1S/C20H32O3/c1-6-8-17(22)20(5)15(12(3)7-2)10-9-14-18(20)13(4)11-16(21)19(14)23/h6,8-10,12-16,18-19,21,23H,7,11H2,1-5H3/b8-6+/t12-,13-,14-,15-,16-,18+,19+,20-/m1/s1

InChI Key

TYAHOTSECGQFPS-KNJHQLMTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enones

Alternative Parents

Substituents

Enone
Cyclic alcohol
Acryloyl-group
Secondary alcohol
Ketone
1,2-diol
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.055 g/L	ALOGPS
logP	3.57	ALOGPS
logP	3.92	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.71	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	95.63 m³·mol⁻¹	ChemAxon
Polarizability	37.05 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

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

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
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

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

78437477

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585920

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

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 Eupenicinicol B (MMDBc0010651)

MOL for #<Metabolite:0x0000556b6af7fcf8>

3D MOL for #<Metabolite:0x0000556b6af7fcf8>

3D SDF for #<Metabolite:0x0000556b6af7fcf8>

3D-SDF for #<Metabolite:0x0000556b6af7fcf8>

PDB for #<Metabolite:0x0000556b6af7fcf8>

3D PDB for #<Metabolite:0x0000556b6af7fcf8>

SMILES for #<Metabolite:0x0000556b6af7fcf8>

INCHI for #<Metabolite:0x0000556b6af7fcf8>

Structure for #<Metabolite:0x0000556b6af7fcf8>

3D Structure for #<Metabolite:0x0000556b6af7fcf8>