MiMeDB: Showing metabocard for tri-trans,hepta-cis-undecaprenyl phosphate (MMDBc0056341)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 20:23:15 UTC

Update Date

2022-08-12 20:09:41 UTC

Metabolite ID

MMDBc0056341

Metabolite Identification

Common Name

tri-trans,hepta-cis-undecaprenyl phosphate

Description

tri-trans,hepta-cis-undecaprenyl phosphate, also known as tritrans,polycis-undecaprenol phosphoric acid(2-), belongs to the class of organic compounds known as bactoprenol monophosphates. These are polyprenyl compounds consisting of a monophosphate group substituted by a bactoprenyl moiety. Based on a literature review very few articles have been published on tri-trans,hepta-cis-undecaprenyl phosphate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172222232D          

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M  CHG  2  56  -1  57  -1
M  END


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 66 35  1  0  0  0  0
 67 37  1  0  0  0  0
 68 39  1  0  0  0  0
 69 41  1  0  0  0  0
 70 43  1  0  0  0  0
M  CHG  2  56  -1  57  -1
M  END
> <DATABASE_ID>
MMDBc0056341

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])COP([O-])([O-])=O)=C(\C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C55H91O4P/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-59-60(56,57)58/h23,25,27,29,31,33,35,37,39,41,43H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3,(H2,56,57,58)/p-2/b46-25+,47-27+,48-29+,49-31-,50-33-,51-35-,52-37-,53-39-,54-41-,55-43-

> <INCHI_KEY>
UFPHFKCTOZIAFY-RTRZQXHFSA-L

> <FORMULA>
C55H89O4P

> <MOLECULAR_WEIGHT>
845.288

> <EXACT_MASS>
844.650945504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
149

> <JCHEM_AVERAGE_POLARIZABILITY>
106.32003899095446

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl phosphate

> <JCHEM_LOGP>
17.316245739666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.811862989729707

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.785397553289238

> <JCHEM_POLAR_SURFACE_AREA>
72.42

> <JCHEM_REFRACTIVITY>
274.0350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
33

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0     -46.970 -12.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -46.970  -9.336   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -42.350  -6.668   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -37.730  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -33.110  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -28.490   1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -23.870  -4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -19.250   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -14.630  -4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -10.010   1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.390  -4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -43.890  -9.336   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -39.270  -6.668   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -34.650  -4.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -30.030  -1.334   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -25.410  -1.334   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -20.790  -1.334   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -16.170  -1.334   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -11.550  -1.334   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.930  -1.334   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -44.660 -10.669   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -42.350  -9.336   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -40.040  -8.002   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -37.730  -6.668   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -35.420  -5.335   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -33.110  -4.001   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -30.800  -2.667   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -28.490  -1.334   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0     -26.180   0.000   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -23.870  -1.334   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -21.560  -2.667   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -19.250  -1.334   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0     -16.940   0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0     -14.630  -1.334   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0     -12.320  -2.667   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0     -10.010  -1.334   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -7.700   0.000   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -5.390  -1.334   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -46.200 -10.669   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -41.580  -8.002   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -36.960  -5.335   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0     -32.340  -2.667   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0     -27.720   0.000   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0     -23.100  -2.667   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0     -18.480   0.000   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0     -13.860  -2.667   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -9.240   0.000   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      -4.620  -2.667   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       5.390  -4.001   0.000  0.00  0.00           O-1
HETATM   57  O   UNK     0       3.286  -3.437   0.000  0.00  0.00           O-1
HETATM   58  O   UNK     0       5.954  -1.897   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0       3.850  -1.334   0.000  0.00  0.00           O+0
HETATM   60  P   UNK     0       4.620  -2.667   0.000  0.00  0.00           P+0
HETATM   61  H   UNK     0     -39.270  -9.336   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0     -34.650  -6.668   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0     -30.030  -4.001   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0     -25.410   1.334   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0     -20.790  -4.001   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0     -16.170   1.334   0.000  0.00  0.00           H+0
HETATM   67  H   UNK     0     -11.550  -4.001   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0      -6.930   1.334   0.000  0.00  0.00           H+0
HETATM   69  H   UNK     0      -2.310  -4.001   0.000  0.00  0.00           H+0
HETATM   70  H   UNK     0       2.310   1.334   0.000  0.00  0.00           H+0
CONECT    1   45                                                            
CONECT    2   45                                                            
CONECT    3   46                                                            
CONECT    4   47                                                            
CONECT    5   48                                                            
CONECT    6   49                                                            
CONECT    7   50                                                            
CONECT    8   51                                                            
CONECT    9   52                                                            
CONECT   10   53                                                            
CONECT   11   54                                                            
CONECT   12   55                                                            
CONECT   13   23   24                                                       
CONECT   14   25   26                                                       
CONECT   15   27   28                                                       
CONECT   16   29   30                                                       
CONECT   17   31   32                                                       
CONECT   18   33   34                                                       
CONECT   19   35   36                                                       
CONECT   20   37   38                                                       
CONECT   21   39   40                                                       
CONECT   22   41   42                                                       
CONECT   23   13   45                                                       
CONECT   24   13   46                                                       
CONECT   25   14   46   61                                                  
CONECT   26   14   47                                                       
CONECT   27   15   47   62                                                  
CONECT   28   15   48                                                       
CONECT   29   16   48   63                                                  
CONECT   30   16   49                                                       
CONECT   31   17   49   64                                                  
CONECT   32   17   50                                                       
CONECT   33   18   50   65                                                  
CONECT   34   18   51                                                       
CONECT   35   19   51   66                                                  
CONECT   36   19   52                                                       
CONECT   37   20   52   67                                                  
CONECT   38   20   53                                                       
CONECT   39   21   53   68                                                  
CONECT   40   21   54                                                       
CONECT   41   22   54   69                                                  
CONECT   42   22   55                                                       
CONECT   43   44   55   70                                                  
CONECT   44   43   59                                                       
CONECT   45    1    2   23                                                  
CONECT   46    3   24   25                                                  
CONECT   47    4   26   27                                                  
CONECT   48    5   28   29                                                  
CONECT   49    6   30   31                                                  
CONECT   50    7   32   33                                                  
CONECT   51    8   34   35                                                  
CONECT   52    9   36   37                                                  
CONECT   53   10   38   39                                                  
CONECT   54   11   40   41                                                  
CONECT   55   12   42   43                                                  
CONECT   56   60                                                            
CONECT   57   60                                                            
CONECT   58   60                                                            
CONECT   59   44   60                                                       
CONECT   60   56   57   58   59                                             
CONECT   61   25                                                            
CONECT   62   27                                                            
CONECT   63   29                                                            
CONECT   64   31                                                            
CONECT   65   33                                                            
CONECT   66   35                                                            
CONECT   67   37                                                            
CONECT   68   39                                                            
CONECT   69   41                                                            
CONECT   70   43                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  138    0
END

Synonyms

Value	Source
Tritrans,heptacis-undecaprenol phosphate(2-)	ChEBI
Tritrans,polycis-undecaprenol phosphate(2-)	ChEBI
Tritrans,polycis-undecaprenyl phosphate(2-)	ChEBI
Tritrans,heptacis-undecaprenol phosphoric acid(2-)	Generator
Tritrans,polycis-undecaprenol phosphoric acid(2-)	Generator
Tritrans,polycis-undecaprenyl phosphoric acid(2-)	Generator
Tri-trans,hepta-cis-undecaprenyl phosphoric acid	Generator

Molecular Formula

C₅₅H₈₉O₄P

Average Mass

845.288

Monoisotopic Mass

844.650945504

IUPAC Name

(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl phosphate

Traditional Name

(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30E,34E,38E)-3,7,11,15,19,23,27,31,35,39,43-undecamethyltetratetraconta-2,6,10,14,18,22,26,30,34,38,42-undecaen-1-yl phosphate

CAS Registry Number

Not Available

SMILES

[H]\C(CC\C(C)=C(/[H])CC\C(C)=C(/[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])CC\C(C)=C(\[H])COP([O-])([O-])=O)=C(\C)CCC=C(C)C

InChI Identifier

InChI=1S/C55H91O4P/c1-45(2)23-13-24-46(3)25-14-26-47(4)27-15-28-48(5)29-16-30-49(6)31-17-32-50(7)33-18-34-51(8)35-19-36-52(9)37-20-38-53(10)39-21-40-54(11)41-22-42-55(12)43-44-59-60(56,57)58/h23,25,27,29,31,33,35,37,39,41,43H,13-22,24,26,28,30,32,34,36,38,40,42,44H2,1-12H3,(H2,56,57,58)/p-2/b46-25+,47-27+,48-29+,49-31-,50-33-,51-35-,52-37-,53-39-,54-41-,55-43-

InChI Key

UFPHFKCTOZIAFY-RTRZQXHFSA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bactoprenol monophosphates. These are polyprenyl compounds consisting of a monophosphate group substituted by a bactoprenyl moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Polyprenols

Direct Parent

Bactoprenol monophosphates

Alternative Parents

Substituents

Polyterpenoid
Bactoprenol monophosphate
Polyprenyl monophosphate
Isoprenoid phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic anion
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organophosphate oxoanion (CHEBI:70763 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	17.32	ChemAxon
pKa (Strongest Acidic)	1.79	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	72.42 Å²	ChemAxon
Rotatable Bond Count	33	ChemAxon
Refractivity	274.04 m³·mol⁻¹	ChemAxon
Polarizability	106.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Deposition Date	View
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

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	Proteobacteria	1	Human ; Human feces

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

24603914

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45105125

PDB ID

Not Available

ChEBI ID

70763

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for tri-trans,hepta-cis-undecaprenyl phosphate (MMDBc0056341)

MOL for #<Metabolite:0x00007fdb0d048040>

3D MOL for #<Metabolite:0x00007fdb0d048040>

3D SDF for #<Metabolite:0x00007fdb0d048040>

3D-SDF for #<Metabolite:0x00007fdb0d048040>

PDB for #<Metabolite:0x00007fdb0d048040>

3D PDB for #<Metabolite:0x00007fdb0d048040>

SMILES for #<Metabolite:0x00007fdb0d048040>

INCHI for #<Metabolite:0x00007fdb0d048040>

Structure for #<Metabolite:0x00007fdb0d048040>

3D Structure for #<Metabolite:0x00007fdb0d048040>