MiMeDB: Showing metabocard for 3-(all-trans-triprenyl)benzene-1,2-diol (MMDBc0031888)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:53:21 UTC

Update Date

2022-08-31 18:25:46 UTC

Metabolite ID

MMDBc0031888

Metabolite Identification

Common Name

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

Description

3-(all-trans-triprenyl)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-triprenyl)benzene-1,2-diol = S-adenosyl-L-homocysteine + 2-methoxy-6-(all-trans-triprenyl)phenol.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 10221219202D          

 21 21  0  0  0  0            999 V2000
    2.1027   -0.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5317   -0.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2462   -3.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2462   -2.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5317   -4.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8172   -1.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5317   -1.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8172   -0.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5317   -2.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8172   -3.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8172   -2.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1027   -4.2203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1027   -2.5703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0407   -0.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738    0.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3883   -0.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6738   -0.0953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7551   -2.5703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4696   -1.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0407   -1.3328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7551   -1.7453    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
M  END
> <DATABASE_ID>
MMDBc0031888

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O2/c1-14(2)8-9-15(3)10-11-16(4)12-13-17-6-5-7-18(20)19(17)21/h5-8,10,12,20-21H,9,11,13H2,1-4H3/b15-10+,16-12+

> <INCHI_KEY>
VNKKQNZCBITKGE-NCZFFCEISA-N

> <FORMULA>
C19H26O2

> <MOLECULAR_WEIGHT>
286.4085

> <EXACT_MASS>
286.193280076

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.25468214663124

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(2E,5E)-3,6,9-trimethyldeca-2,5,8-trien-1-yl]benzene-1,2-diol

> <ALOGPS_LOGP>
5.79

> <JCHEM_LOGP>
5.524973392

> <ALOGPS_LOGS>
-4.47

> <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>
92.6658

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.65e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2E,5E)-3,6,9-trimethyldeca-2,5,8-trien-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       3.925  -0.178   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.593  -0.178   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.926  -7.108   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.926  -5.568   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.593  -7.878   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.259  -2.488   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.593  -3.258   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.259  -0.948   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.593  -4.798   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.259  -7.108   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.259  -5.568   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.925  -7.878   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       3.925  -4.798   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.076  -0.948   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.258   1.362   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.591  -0.948   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.258  -0.178   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.410  -4.798   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.743  -2.488   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.076  -2.488   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.410  -3.258   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                                                            
CONECT   19   21                                                            
CONECT   20   14   21                                                       
CONECT   21   18   19   20                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

Synonyms

Not Available

Molecular Formula

C₁₉H₂₆O₂

Average Mass

286.4085

Monoisotopic Mass

286.193280076

IUPAC Name

3-[(2E,5E)-3,6,9-trimethyldeca-2,5,8-trien-1-yl]benzene-1,2-diol

Traditional Name

3-[(2E,5E)-3,6,9-trimethyldeca-2,5,8-trien-1-yl]benzene-1,2-diol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C19H26O2/c1-14(2)8-9-15(3)10-11-16(4)12-13-17-6-5-7-18(20)19(17)21/h5-8,10,12,20-21H,9,11,13H2,1-4H3/b15-10+,16-12+

InChI Key

VNKKQNZCBITKGE-NCZFFCEISA-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	0.0096 g/L	ALOGPS
logP	5.79	ALOGPS
logP	5.52	ChemAxon
logS	-4.5	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	6	ChemAxon
Refractivity	92.67 m³·mol⁻¹	ChemAxon
Polarizability	34.25 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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_2_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1590000000-9bcd361015ca889d7555	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abi-2910000000-b82f80ea9cf11bf479b0	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mo-9600000000-e23aa6fa8007e7872522	2015-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1590000000-9bcd361015ca889d7555	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0abi-2910000000-b82f80ea9cf11bf479b0	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mo-9600000000-e23aa6fa8007e7872522	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-ff14cb0a6053f9c64a1a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0190000000-525e5ba3dd15b751a978	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-3930000000-d03faa8e0f2491c1c6d5	2015-09-15	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

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

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

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-triprenyl)benzene-1,2-diol (MMDBc0031888)

MOL for #<Metabolite:0x00007fecd35e25f0>

3D MOL for #<Metabolite:0x00007fecd35e25f0>

3D SDF for #<Metabolite:0x00007fecd35e25f0>

3D-SDF for #<Metabolite:0x00007fecd35e25f0>

PDB for #<Metabolite:0x00007fecd35e25f0>

3D PDB for #<Metabolite:0x00007fecd35e25f0>

SMILES for #<Metabolite:0x00007fecd35e25f0>

INCHI for #<Metabolite:0x00007fecd35e25f0>

Structure for #<Metabolite:0x00007fecd35e25f0>

3D Structure for #<Metabolite:0x00007fecd35e25f0>