MiMeDB: Showing metabocard for 3-(all-trans-tetraprenyl)benzene-1,2-diol (MMDBc0031887)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:53:19 UTC

Update Date

2022-08-31 18:25:45 UTC

Metabolite ID

MMDBc0031887

Metabolite Identification

Common Name

3-(all-trans-tetraprenyl)benzene-1,2-diol

Description

3-(all-trans-tetraprenyl)benzene-1,2-diol is involved in the ubiquinone biosynthetic pathway. It is a substrate for the 3-demethylubiquinone-9 3-methyltransferase that catalyses the following reaction: S-adenosyl-L-methionine + 3-(all-trans-tetraprenyl)benzene-1,2-diol = S-adenosyl-L-homocysteine + 2-methoxy-6-(all-trans-tetraprenyl)phenol.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 10221219202D          

 25 25  0  0  0  0            999 V2000
    1.8741   -0.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -0.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0175   -3.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0175   -2.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -4.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886   -1.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -1.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886   -0.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3031   -2.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886   -3.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5886   -2.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8741   -4.2203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8741   -2.5703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693   -0.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452    0.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1596   -0.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -0.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9838   -2.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6982   -1.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693   -1.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9838   -1.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4452   -4.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9838   -4.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693   -2.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2693   -3.8078    0.0000 C   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
  7  6  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  6  2  0  0  0  0
  9  4  1  0  0  0  0
  9  7  1  0  0  0  0
 10  5  2  0  0  0  0
 11  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
  1 16  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 17 16  2  0  0  0  0
 14 20  1  0  0  0  0
 21 18  1  0  0  0  0
 21 19  1  0  0  0  0
 21 20  2  0  0  0  0
 18 24  1  0  0  0  0
 25 22  1  0  0  0  0
 25 23  1  0  0  0  0
 25 24  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031887

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)=CC\C(C)=C\C\C(C)=C\C\C(C)=C\CC1=C(O)C(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H32O2/c1-17(2)9-10-18(3)11-12-19(4)13-14-20(5)15-16-21-7-6-8-22(24)23(21)25/h6-9,11,13,15,24-25H,10,12,14,16H2,1-5H3/b18-11+,19-13+,20-15+

> <INCHI_KEY>
FQASEYLIIUVQGW-QIRCYJPOSA-N

> <FORMULA>
C23H32O2

> <MOLECULAR_WEIGHT>
340.499

> <EXACT_MASS>
340.240230268

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
41.478426768208166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2E,5E,8E)-3,6,9,12-tetramethyltrideca-2,5,8,11-tetraen-1-yl]benzene-1,2-diol

> <ALOGPS_LOGP>
6.56

> <JCHEM_LOGP>
6.740119002

> <ALOGPS_LOGS>
-5.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.663643999598339

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.206228182645257

> <JCHEM_PKA_STRONGEST_BASIC>
-6.2954389432422575

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
111.8674

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2E,5E,8E)-3,6,9,12-tetramethyltrideca-2,5,8,11-tetraen-1-yl]benzene-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-OCT-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-OCT-12         0                                  
HETATM    1  C   UNK     0       3.498  -0.178   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.166  -0.178   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.499  -7.108   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.499  -5.568   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.166  -7.878   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.832  -2.488   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.166  -3.258   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.832  -0.948   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.166  -4.798   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.832  -7.108   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.832  -5.568   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.498  -7.878   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.498  -4.798   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.503  -0.948   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.831   1.362   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.165  -0.948   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.831  -0.178   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.836  -4.798   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.170  -2.488   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.503  -2.488   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.836  -3.258   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.831  -7.878   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.836  -7.878   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.503  -5.568   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.503  -7.108   0.000  0.00  0.00           C+0
CONECT    1    8   16                                                       
CONECT    2    8                                                            
CONECT    3    4    5                                                       
CONECT    4    3    9                                                       
CONECT    5    3   10                                                       
CONECT    6    7    8                                                       
CONECT    7    6    9                                                       
CONECT    8    1    2    6                                                  
CONECT    9    4    7   11                                                  
CONECT   10    5   11   12                                                  
CONECT   11    9   10   13                                                  
CONECT   12   10                                                            
CONECT   13   11                                                            
CONECT   14   17   20                                                       
CONECT   15   17                                                            
CONECT   16    1   17                                                       
CONECT   17   14   15   16                                                  
CONECT   18   21   24                                                       
CONECT   19   21                                                            
CONECT   20   14   21                                                       
CONECT   21   18   19   20                                                  
CONECT   22   25                                                            
CONECT   23   25                                                            
CONECT   24   18   25                                                       
CONECT   25   22   23   24                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

Synonyms

Not Available

Molecular Formula

C₂₃H₃₂O₂

Average Mass

340.499

Monoisotopic Mass

340.240230268

IUPAC Name

3-[(2E,5E,8E)-3,6,9,12-tetramethyltrideca-2,5,8,11-tetraen-1-yl]benzene-1,2-diol

Traditional Name

3-[(2E,5E,8E)-3,6,9,12-tetramethyltrideca-2,5,8,11-tetraen-1-yl]benzene-1,2-diol

CAS Registry Number

Not Available

SMILES

CC(C)=CC\C(C)=C\C\C(C)=C\C\C(C)=C\CC1=C(O)C(O)=CC=C1

InChI Identifier

InChI=1S/C23H32O2/c1-17(2)9-10-18(3)11-12-19(4)13-14-20(5)15-16-21-7-6-8-22(24)23(21)25/h6-9,11,13,15,24-25H,10,12,14,16H2,1-5H3/b18-11+,19-13+,20-15+

InChI Key

FQASEYLIIUVQGW-QIRCYJPOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	0.0031 g/L	ALOGPS
logP	6.56	ALOGPS
logP	6.74	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	111.87 m³·mol⁻¹	ChemAxon
Polarizability	41.48 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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	splash10-0006-1669000000-d5bf447c1dcdad968fda	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ab9-2940000000-71f078e315c2c64b4ee7	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9740000000-0b730f6f01ba17ff70e9	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-7e7be831623a14f12d21	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0119000000-6fc8e70777099c34214b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-2932000000-1781eaaae0445b509861	2015-09-15	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum

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
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

Other Exposures

Source Type	Activity	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Sajed T, Marcu A, Ramirez M, Pon A, Guo AC, Knox C, Wilson M, Grant JR, Djoumbou Y, Wishart DS: ECMDB 2.0: A richer resource for understanding the biochemistry of E. coli. Nucleic Acids Res. 2016 Jan 4;44(D1):D495-501. doi: 10.1093/nar/gkv1060. Epub 2015 Oct 19. [PubMed:26481353 ]

Showing metabocard for 3-(all-trans-tetraprenyl)benzene-1,2-diol (MMDBc0031887)

MOL for #<Metabolite:0x00007fca40ea1048>

3D MOL for #<Metabolite:0x00007fca40ea1048>

3D SDF for #<Metabolite:0x00007fca40ea1048>

3D-SDF for #<Metabolite:0x00007fca40ea1048>

PDB for #<Metabolite:0x00007fca40ea1048>

3D PDB for #<Metabolite:0x00007fca40ea1048>

SMILES for #<Metabolite:0x00007fca40ea1048>

INCHI for #<Metabolite:0x00007fca40ea1048>

Structure for #<Metabolite:0x00007fca40ea1048>

3D Structure for #<Metabolite:0x00007fca40ea1048>