MiMeDB: Showing metabocard for Ubiquinone-1 (MMDBc0030371)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:05:39 UTC

Update Date

2022-08-31 17:49:51 UTC

Metabolite ID

MMDBc0030371

Metabolite Identification

Common Name

Ubiquinone-1

Description

Ubiquinone-1 is a member of the chemical class known as Polyprenylbenzoquinones. These are compounds containing a polyisoprene chain attached to a quinone at the second ring position. Ubiquione-1 has just 1 isoprene unit. Normally in E. coli the active form of Ubiquinone has 8 isoprene units (Ubiquinone-8) and in humans it normally has 10. Ubiquinone-1 is a ‚Äúfailed‚Äù or incomplete version of Ubiquinone 8 that arises from conjugation by a shortened prenyl tail via 4-hydroxybenzoate polyprenyltransferase. Ubiquionone is involved in cellular respiration. It is fat-soluble and is therefore mobile in cellular membranes; it plays a unique role in the electron transport chain (ETC). In the inner bacterial membrane, electrons from NADH and succinate pass through the ETC to the oxygen, which is then reduced to water. The transfer of electrons through ETC results in the pumping of H+ across the membrane creating a proton gradient across the membrane, which is used by ATP synthase (located on the membrane) to generate ATP.

Structure

MOL SDF PDB SMILES InChI

      
  Mrv1533005201511402D          

 23 23  0  0  0  0            999 V2000
   -1.0717    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2151   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2151    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
  4 13  1  0  0  0  0
  3 14  1  0  0  0  0
 15 14  1  4  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0030371

> <DATABASE_NAME>
MIME

> <SMILES>
COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)C)C(O)=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O4/c1-12(2)8-7-9-13(3)10-11-15-14(4)16(20)18(22-5)19(23-6)17(15)21/h8,10,20-21H,7,9,11H2,1-6H3

> <INCHI_KEY>
RNUCUWWMTTWKAH-UHFFFAOYSA-N

> <FORMULA>
C19H28O4

> <MOLECULAR_WEIGHT>
320.429

> <EXACT_MASS>
320.198759382

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.22216172159473

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3,7-dimethylocta-2,6-dien-1-yl)-5,6-dimethoxy-3-methylbenzene-1,4-diol

> <ALOGPS_LOGP>
4.41

> <JCHEM_LOGP>
4.952475305

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.153761006645082

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.266548299637904

> <JCHEM_PKA_STRONGEST_BASIC>
-4.664919089384427

> <JCHEM_POLAR_SURFACE_AREA>
58.92

> <JCHEM_REFRACTIVITY>
96.03279999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,7-dimethylocta-2,6-dien-1-yl)-5,6-dimethoxy-3-methylbenzene-1,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 20-MAY-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-15         0                                  
HETATM    1  C   UNK     0      -2.001   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.001  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.667  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.667  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.334  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.668  -1.540   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -4.668  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -6.002  -3.850   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.001  -6.160   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.334  -6.930   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.667  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.667  -1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.001   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.334   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.001   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.334   3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.334   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.668   5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.668   6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.002   4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7    9                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9                                                            
CONECT   11    5   12                                                       
CONECT   12   11                                                            
CONECT   13    4                                                            
CONECT   14    3   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

Synonyms

Not Available

Molecular Formula

C₁₉H₂₈O₄

Average Mass

320.429

Monoisotopic Mass

320.198759382

IUPAC Name

2-(3,7-dimethylocta-2,6-dien-1-yl)-5,6-dimethoxy-3-methylbenzene-1,4-diol

Traditional Name

2-(3,7-dimethylocta-2,6-dien-1-yl)-5,6-dimethoxy-3-methylbenzene-1,4-diol

CAS Registry Number

727-81-1

SMILES

COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)C)C(O)=C1OC

InChI Identifier

InChI=1S/C19H28O4/c1-12(2)8-7-9-13(3)10-11-15-14(4)16(20)18(22-5)19(23-6)17(15)21/h8,10,20-21H,7,9,11H2,1-6H3

InChI Key

RNUCUWWMTTWKAH-UHFFFAOYSA-N

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as ubiquinols. These are coenzyme Q derivatives containing a 5, 6-dimethoxy-3-methylbenzene-1,4-diol moiety to which an isoprenyl group is attached at ring position 2(or 6).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Ubiquinols

Alternative Parents

Substituents

Ubiquinol skeleton
Aromatic monoterpenoid
Methoxyphenol
Monocyclic monoterpenoid
Monoterpenoid
O-dimethoxybenzene
Dimethoxybenzene
Anisole
Phenoxy compound
Hydroquinone
M-cresol
Methoxybenzene
O-cresol
Phenol ether
Alkyl aryl ether
Phenol
Toluene
Monocyclic benzene moiety
Benzenoid
Ether
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

a ubiquinol (QH2 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.012 g/L	ALOGPS
logP	4.41	ALOGPS
logP	4.95	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	10.27	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.92 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	96.03 m³·mol⁻¹	ChemAxon
Polarizability	36.22 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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	Data Source	Reference
MMDBr0000520	2-Decaprenyl-5-Hydroxy-6-Methoxy-3-Methyl-1,4-Benzoquinone	S-Adenosylhomocysteine	coenzyme Q3 methyltransferase	VMH	10777520 11051212 1965190 7380842
MMDBr0000557	Ferricytochrome c	Ferrocytochrome c	Not Available	VMH	10453733 11047755
MMDBr0000680	4,5-Dihydroorotic acid	Orotic acid	dihydroorotate dehydrogenase (quinone)	VMH	10727948 9693067
MMDBr0001699	Ubiquinone-1	Ubiquinol-10	Not Available	VMH	19185523 19185524 7180843
MMDBr0002267	Ubiquinone-1	Ubiquinol-10	thioredoxin reductase 1	VMH	12435734 8577704 8999974
MMDBr0002268	Ubiquinone-1	Ubiquinol-10	thioredoxin reductase 1	VMH	12435734 8577704 8999974
MMDBr0002485	Glycerol 3-phosphate	Dihydroxyacetone phosphate	glycerol-3-phosphate dehydrogenase 2 (mitochondrial)	VMH	11955283 2115809 2923620 3338458 340460 8401296 8549872 8579375 9171333 9244403 9559543
MMDBr0002507	Palmityl-CoA	(2E)-Hexadecenoyl-CoA	acyl-CoA dehydrogenase, long chain	VMH	17603022 1774065 3597357 6240978 7876265
MMDBr0002577	Ubiquinone-1	Fumaric acid	succinate dehydrogenase complex, subunit A, flavoprotein (Fp)	VMH	2843227
MMDBr0002588	Glutaryl-CoA	Crotonoyl-CoA	glutaryl-CoA dehydrogenase	VMH	3081514
MMDBr0002601	Isobutyryl-CoA	Methacrylyl-CoA	acyl-CoA dehydrogenase, C-2 to C-3 short chain	VMH	12855692 3597357 6401712 6874697
MMDBr0002618	2-Methylbutyryl-CoA	Tiglyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	6401712
MMDBr0002651	Isovaleryl-CoA	3-Methylcrotonyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	3597357 9214289
MMDBr0002663	Propionyl-CoA	Acrylyl-CoA	acyl-CoA dehydrogenase, C-4 to C-12 straight chain	VMH	10502673 3597357 4062874
MMDBr0002959	Butyryl-CoA	Crotonoyl-CoA	acyl-CoA oxidase 1, palmitoyl	VMH	17603022 1774065 3597357 6240978 7876265
MMDBr0002960	Lauroyl-CoA	(2E)-Dodecenoyl-CoA	acyl-CoA oxidase 1, palmitoyl	VMH	17603022 1774065 3597357 6240978 7876265
MMDBr0002961	Octanoyl-CoA	(2E)-Octenoyl-CoA	acyl-CoA oxidase 1, palmitoyl	VMH	17603022 1774065 3597357 6240978 7876265
MMDBr0002962	Ubiquinone-1	(2E)-Tetradecenoyl-CoA	acyl-CoA oxidase 1, palmitoyl	VMH	17603022 1774065 3597357 6240978 7876265
MMDBr0002963	Hexanoyl-CoA	trans-2-Hexenoyl-CoA	acyl-CoA oxidase 1, palmitoyl	VMH	17603022 1774065 3597357 6240978 7876265
MMDBr0002964	Decanoyl-CoA (N-C10:0CoA)	(2E)-Decenoyl-CoA	acyl-CoA oxidase 1, palmitoyl	VMH	17603022 1774065 3597357 6240978 7876265
MMDBr0002965	L-Proline	L-D-1-Pyrroline-5-carboxylic acid	proline dehydrogenase (oxidase) 1	VMH	18506409
MMDBr0004232	Alpha-Tocopheryl Hydroquinone	alpha-Tocopherolquinone	Not Available	VMH	9223282
MMDBr0005471	Ubiquinone-1	Ubiquinol-10	electron-transfer-flavoprotein, alpha polypeptide	VMH	30371894
MMDBr0010374	alpha-Tocopherol	alpha-Tocopherolquinone	Not Available	VMH	30371894
MMDBr0010375	Alpha-Tocopheryl Hydroquinone	alpha-Tocopherolquinone	Not Available	VMH	30371894
MMDBr0012612	Ferricytochrome c	Ferrocytochrome c	cytochrome c-1	VMH	30371894
MMDBr0012614	Ubiquinone-1	Ubiquinol-10	mitochondrially encoded NADH dehydrogenase 1	VMH	30371894

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
Human Feces	Detected but not Quantified									HMDB

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

1033

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1062

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Kita K, Takamiya S, Furushima R, Ma YC, Suzuki H, Ozawa T, Oya H: Electron-transfer complexes of Ascaris suum muscle mitochondria. III. Composition and fumarate reductase activity of complex II. Biochim Biophys Acta. 1988 Sep 14;935(2):130-40. doi: 10.1016/0005-2728(88)90210-1. [PubMed:2843227 ]
Lenich AC, Goodman SI: The purification and characterization of glutaryl-coenzyme A dehydrogenase from porcine and human liver. J Biol Chem. 1986 Mar 25;261(9):4090-6. [PubMed:3081514 ]
Ikeda Y, Dabrowski C, Tanaka K: Separation and properties of five distinct acyl-CoA dehydrogenases from rat liver mitochondria. Identification of a new 2-methyl branched chain acyl-CoA dehydrogenase. J Biol Chem. 1983 Jan 25;258(2):1066-76. [PubMed:6401712 ]
Neuzil J, Witting PK, Stocker R: Alpha-tocopheryl hydroquinone is an efficient multifunctional inhibitor of radical-initiated oxidation of low density lipoprotein lipids. Proc Natl Acad Sci U S A. 1997 Jul 22;94(15):7885-90. doi: 10.1073/pnas.94.15.7885. [PubMed:9223282 ]
Hu CA, Bart Williams D, Zhaorigetu S, Khalil S, Wan G, Valle D: Functional genomics and SNP analysis of human genes encoding proline metabolic enzymes. Amino Acids. 2008 Nov;35(4):655-64. doi: 10.1007/s00726-008-0107-9. Epub 2008 May 28. [PubMed:18506409 ]
Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for Ubiquinone-1 (MMDBc0030371)

MOL for #<Metabolite:0x00007f46e1185d38>

3D MOL for #<Metabolite:0x00007f46e1185d38>

3D SDF for #<Metabolite:0x00007f46e1185d38>

3D-SDF for #<Metabolite:0x00007f46e1185d38>

PDB for #<Metabolite:0x00007f46e1185d38>

3D PDB for #<Metabolite:0x00007f46e1185d38>

SMILES for #<Metabolite:0x00007f46e1185d38>

INCHI for #<Metabolite:0x00007f46e1185d38>

Structure for #<Metabolite:0x00007f46e1185d38>

3D Structure for #<Metabolite:0x00007f46e1185d38>