MiMeDB: Showing metabocard for Penikellide B (MMDBc0004496)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 22:27:08 UTC

Update Date

2022-08-31 06:22:32 UTC

Metabolite ID

MMDBc0004496

Metabolite Identification

Common Name

Penikellide B

Description

6-{2-[(acetyloxy)methyl]-6-hydroxy-4-methylphenoxy}-2-methoxy-3-[(1S)-1-methoxy-3-methylbutyl]benzoic acid belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group. Based on a literature review very few articles have been published on 6-{2-[(acetyloxy)methyl]-6-hydroxy-4-methylphenoxy}-2-methoxy-3-[(1S)-1-methoxy-3-methylbutyl]benzoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152100272D          

 33 34  0  0  1  0            999 V2000
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    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
    3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 C   0  0  1  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
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 O   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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  9  1  0  0  0  0
 14  3  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15  4  1  0  0  0  0
 16 10  1  0  0  0  0
 16 12  1  0  0  0  0
 17  7  1  0  0  0  0
 18 11  2  0  0  0  0
 19  8  1  0  0  0  0
 20  9  1  0  0  0  0
 20 17  1  0  0  0  0
 21 19  2  0  0  0  0
 22 16  2  0  0  0  0
 22 18  1  0  0  0  0
 23 17  2  0  0  0  0
 23 21  1  0  0  0  0
 24 21  1  0  0  0  0
 25 15  2  0  0  0  0
 26 18  1  0  0  0  0
 27 24  2  0  0  0  0
 28 24  1  0  0  0  0
 29  5  1  0  0  0  0
 20 29  1  1  0  0  0
 30  6  1  0  0  0  0
 30 23  1  0  0  0  0
 31 12  1  0  0  0  0
 31 15  1  0  0  0  0
 32 19  1  0  0  0  0
 32 22  1  0  0  0  0
 20 33  1  1  0  0  0
M  END


  Mrv1652305152100272D          

 33 34  0  0  1  0            999 V2000
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    0.4125    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
    3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    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
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.1250    0.0000 C   0  0  1  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
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    1.6500    0.0000 O   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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  9  1  0  0  0  0
 14  3  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15  4  1  0  0  0  0
 16 10  1  0  0  0  0
 16 12  1  0  0  0  0
 17  7  1  0  0  0  0
 18 11  2  0  0  0  0
 19  8  1  0  0  0  0
 20  9  1  0  0  0  0
 20 17  1  0  0  0  0
 21 19  2  0  0  0  0
 22 16  2  0  0  0  0
 22 18  1  0  0  0  0
 23 17  2  0  0  0  0
 23 21  1  0  0  0  0
 24 21  1  0  0  0  0
 25 15  2  0  0  0  0
 26 18  1  0  0  0  0
 27 24  2  0  0  0  0
 28 24  1  0  0  0  0
 29  5  1  0  0  0  0
 20 29  1  1  0  0  0
 30  6  1  0  0  0  0
 30 23  1  0  0  0  0
 31 12  1  0  0  0  0
 31 15  1  0  0  0  0
 32 19  1  0  0  0  0
 32 22  1  0  0  0  0
 20 33  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0004496

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@](CC(C)C)(OC)C1=C(OC)C(C(O)=O)=C(OC2=C(COC(C)=O)C=C(C)C=C2O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O8/c1-13(2)9-20(29-5)17-7-8-19(21(24(27)28)23(17)30-6)32-22-16(12-31-15(4)25)10-14(3)11-18(22)26/h7-8,10-11,13,20,26H,9,12H2,1-6H3,(H,27,28)/t20-/m0/s1

> <INCHI_KEY>
KHTVQHHROPEJOZ-FQEVSTJZSA-N

> <FORMULA>
C24H30O8

> <MOLECULAR_WEIGHT>
446.496

> <EXACT_MASS>
446.194067926

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
46.49322991633507

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-{2-[(acetyloxy)methyl]-6-hydroxy-4-methylphenoxy}-2-methoxy-3-[(1S)-1-methoxy-3-methylbutyl]benzoic acid

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
4.403538269333332

> <ALOGPS_LOGS>
-4.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.412169193852954

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1793387357534013

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6081803191832598

> <JCHEM_POLAR_SURFACE_AREA>
111.52000000000001

> <JCHEM_REFRACTIVITY>
118.66719999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{2-[(acetyloxy)methyl]-6-hydroxy-4-methylphenoxy}-2-methoxy-3-[(1S)-1-methoxy-3-methylbutyl]benzoic 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       5.335  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.003   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.002   7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668   5.390   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      10.669   3.080   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       9.336   8.470   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0       6.668   6.930   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5   29                                                            
CONECT    6   30                                                            
CONECT    7    8   17                                                       
CONECT    8    7   19                                                       
CONECT    9   13   20                                                       
CONECT   10   14   16                                                       
CONECT   11   14   18                                                       
CONECT   12   16   31                                                       
CONECT   13    1    2    9                                                  
CONECT   14    3   10   11                                                  
CONECT   15    4   25   31                                                  
CONECT   16   10   12   22                                                  
CONECT   17    7   20   23                                                  
CONECT   18   11   22   26                                                  
CONECT   19    8   21   32                                                  
CONECT   20    9   17   29   33                                             
CONECT   21   19   23   24                                                  
CONECT   22   16   18   32                                                  
CONECT   23   17   21   30                                                  
CONECT   24   21   27   28                                                  
CONECT   25   15                                                            
CONECT   26   18                                                            
CONECT   27   24                                                            
CONECT   28   24                                                            
CONECT   29    5   20                                                       
CONECT   30    6   23                                                       
CONECT   31   12   15                                                       
CONECT   32   19   22                                                       
CONECT   33   20                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   68    0
END

Synonyms

Value	Source
6-{2-[(acetyloxy)methyl]-6-hydroxy-4-methylphenoxy}-2-methoxy-3-[(1S)-1-methoxy-3-methylbutyl]benzoate	Generator

Molecular Formula

C₂₄H₃₀O₈

Average Mass

446.496

Monoisotopic Mass

446.194067926

IUPAC Name

6-{2-[(acetyloxy)methyl]-6-hydroxy-4-methylphenoxy}-2-methoxy-3-[(1S)-1-methoxy-3-methylbutyl]benzoic acid

Traditional Name

6-{2-[(acetyloxy)methyl]-6-hydroxy-4-methylphenoxy}-2-methoxy-3-[(1S)-1-methoxy-3-methylbutyl]benzoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](CC(C)C)(OC)C1=C(OC)C(C(O)=O)=C(OC2=C(COC(C)=O)C=C(C)C=C2O)C=C1

InChI Identifier

InChI=1S/C24H30O8/c1-13(2)9-20(29-5)17-7-8-19(21(24(27)28)23(17)30-6)32-22-16(12-31-15(4)25)10-14(3)11-18(22)26/h7-8,10-11,13,20,26H,9,12H2,1-6H3,(H,27,28)/t20-/m0/s1

InChI Key

KHTVQHHROPEJOZ-FQEVSTJZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Diphenylethers

Alternative Parents

Substituents

Diphenylether
Diaryl ether
O-methoxybenzoic acid or derivatives
Benzyloxycarbonyl
Benzoic acid or derivatives
Benzoic acid
Benzylether
Anisole
Phenoxy compound
Benzoyl
M-cresol
Phenol ether
Methoxybenzene
Alkyl aryl ether
Toluene
Phenol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Dicarboxylic acid or derivatives
Carboxylic acid ester
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Carbonyl group
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	0.015 g/L	ALOGPS
logP	4.14	ALOGPS
logP	4.4	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.18	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	111.52 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	118.67 m³·mol⁻¹	ChemAxon
Polarizability	46.49 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

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

78440836

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139584141

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 Penikellide B (MMDBc0004496)

MOL for #<Metabolite:0x00007fecb3d1ec08>

3D MOL for #<Metabolite:0x00007fecb3d1ec08>

3D SDF for #<Metabolite:0x00007fecb3d1ec08>

3D-SDF for #<Metabolite:0x00007fecb3d1ec08>

PDB for #<Metabolite:0x00007fecb3d1ec08>

3D PDB for #<Metabolite:0x00007fecb3d1ec08>

SMILES for #<Metabolite:0x00007fecb3d1ec08>

INCHI for #<Metabolite:0x00007fecb3d1ec08>

Structure for #<Metabolite:0x00007fecb3d1ec08>

3D Structure for #<Metabolite:0x00007fecb3d1ec08>