MiMeDB: Showing metabocard for 4-deoxy-4-formamido-Œ±-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate (MMDBc0032161)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 02:04:55 UTC

Update Date

2022-08-31 18:31:01 UTC

MiMeDB ID

MMDBc0032161

Metabolite Identification

Common Name

4-deoxy-4-formamido-Œ±-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate

Description

4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate is an intermediate in polymyxin resistance pathway in E.coli. It is a substrate in the reaction 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + H2O -> 4-amino-4-deoxy-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + formate. It is also a product for enzyme undecaprenyl phosphate-L-Ara4FN transferase which catalyzes reaction UDP-4-deoxy-4-formamido-beta-L-arabinopyranose + di-trans,octa-cis-undecaprenyl phosphate ‚Üí 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate + UDP (BioCyc compound: CPD0-888).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533005141519332D          

 71 71  0  0  0  0            999 V2000
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M  END


  Mrv1533005141519332D          

 71 71  0  0  0  0            999 V2000
   -4.5535    1.4276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2680    1.0151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 49 50  1  0  0  0  0
 49 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  2  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  2  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  2  0  0  0  0
 62 63  1  0  0  0  0
 63 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  2  0  0  0  0
 66 67  1  0  0  0  0
 54 68  1  0  0  0  0
 58 69  1  0  0  0  0
 62 70  1  0  0  0  0
 66 71  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0032161

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/COP(O)(=O)OC1OCC(NC=O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C61H100NO8P/c1-47(2)23-13-24-48(3)25-14-26-49(4)27-15-28-50(5)29-16-30-51(6)31-17-32-52(7)33-18-34-53(8)35-19-36-54(9)37-20-38-55(10)39-21-40-56(11)41-22-42-57(12)43-44-69-71(66,67)70-61-60(65)59(64)58(45-68-61)62-46-63/h23,25,27,29,31,33,35,37,39,41,43,46,58-61,64-65H,13-22,24,26,28,30,32,34,36,38,40,42,44-45H2,1-12H3,(H,62,63)(H,66,67)/b48-25+,49-27+,50-29-,51-31-,52-33-,53-35-,54-37-,55-39-,56-41-,57-43-

> <INCHI_KEY>
KDTATMYQJZYGGT-QTBHONTMSA-N

> <FORMULA>
C61H100NO8P

> <MOLECULAR_WEIGHT>
1006.444

> <EXACT_MASS>
1005.718656182

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
171

> <JCHEM_AVERAGE_POLARIZABILITY>
122.12399858137871

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(5-formamido-3,4-dihydroxyoxan-2-yl)oxy]({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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]oxy})phosphinic acid

> <ALOGPS_LOGP>
9.01

> <JCHEM_LOGP>
15.573845353333335

> <ALOGPS_LOGS>
-6.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.335766874622099

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.5783535989509265

> <JCHEM_PKA_STRONGEST_BASIC>
-1.162886243227626

> <JCHEM_POLAR_SURFACE_AREA>
134.55

> <JCHEM_REFRACTIVITY>
309.0711

> <JCHEM_ROTATABLE_BOND_COUNT>
36

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.43e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5-formamido-3,4-dihydroxyoxan-2-yl)oxy[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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]oxyphosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-15         0                                  
HETATM    1  O   UNK     0      -8.500   2.665   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -9.834   1.895   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.834   0.355   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.500  -0.415   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.166   0.355   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.166   1.895   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -8.500  -1.955   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0     -11.167  -0.415   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      -5.833  -0.415   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0     -12.501   1.894   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0     -12.501   0.354   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -5.833   2.665   0.000  0.00  0.00           O+0
HETATM   13  P   UNK     0      -4.499   1.895   0.000  0.00  0.00           P+0
HETATM   14  O   UNK     0      -4.499   0.355   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.559   3.483   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -3.468   2.428   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.171   1.597   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.243   0.059   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.946  -0.772   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.421  -0.065   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.018  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.718  -0.895   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.647  -2.434   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.944  -3.265   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.872  -4.803   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.311  -2.557   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.608  -3.388   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.537  -4.927   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.833  -5.757   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.762  -7.296   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.201  -5.050   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.498  -5.881   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.426  -7.419   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.723  -8.250   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.652  -9.788   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      12.091  -7.543   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.388  -8.373   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.316  -9.912   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      14.613 -10.743   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      14.542 -12.281   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      15.981 -10.035   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      17.277 -10.866   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      17.206 -12.405   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      18.503 -13.235   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      18.432 -14.774   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      19.871 -12.528   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      21.167 -13.359   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      21.096 -14.897   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      22.393 -15.728   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      22.321 -17.266   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      23.761 -15.021   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      25.057 -15.852   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      24.986 -17.390   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      26.282 -18.221   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      27.313 -17.076   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      28.819 -17.397   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      28.049 -16.063   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      28.819 -14.729   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      28.049 -13.396   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      28.819 -12.062   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      28.049 -10.728   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      28.819  -9.395   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      28.049  -8.061   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      28.819  -6.727   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      28.049  -5.393   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      28.819  -4.060   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      28.049  -2.726   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0      26.488 -19.747   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      30.359 -14.729   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      30.359  -9.395   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      30.359  -4.060   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    3    1                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1   12                                                  
CONECT    7    4                                                            
CONECT    8    3   11                                                       
CONECT    9    5                                                            
CONECT   10   11                                                            
CONECT   11   10    8                                                       
CONECT   12    6   13                                                       
CONECT   13   12   16   15   14                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   13   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19   22                                                       
CONECT   21   19                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55   68                                                  
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59   69                                                  
CONECT   59   58   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63   70                                                  
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67   71                                                  
CONECT   67   66                                                            
CONECT   68   54                                                            
CONECT   69   58                                                            
CONECT   70   62                                                            
CONECT   71   66                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  142    0
END

Synonyms

Value	Source
4-Deoxy-4-formamido-α-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphoric acid	Generator

Chemical Formula

C₆₁H₁₀₀NO₈P

Average Molecular Weight

1006.444

Monoisotopic Molecular Weight

1005.718656182

IUPAC Name

[(5-formamido-3,4-dihydroxyoxan-2-yl)oxy]({[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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]oxy})phosphinic acid

Traditional Name

(5-formamido-3,4-dihydroxyoxan-2-yl)oxy[(2Z,6Z,10Z,14Z,18Z,22Z,26Z,30Z,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]oxyphosphinic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/CC\C(C)=C/COP(O)(=O)OC1OCC(NC=O)C(O)C1O

InChI Identifier

InChI=1S/C61H100NO8P/c1-47(2)23-13-24-48(3)25-14-26-49(4)27-15-28-50(5)29-16-30-51(6)31-17-32-52(7)33-18-34-53(8)35-19-36-54(9)37-20-38-55(10)39-21-40-56(11)41-22-42-57(12)43-44-69-71(66,67)70-61-60(65)59(64)58(45-68-61)62-46-63/h23,25,27,29,31,33,35,37,39,41,43,46,58-61,64-65H,13-22,24,26,28,30,32,34,36,38,40,42,44-45H2,1-12H3,(H,62,63)(H,66,67)/b48-25+,49-27+,50-29-,51-31-,52-33-,53-35-,54-37-,55-39-,56-41-,57-43-

InChI Key

KDTATMYQJZYGGT-QTBHONTMSA-N

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
Dialkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
Monosaccharide
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidic acid derivative
Carboximidic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00064 g/L	ALOGPS
logP	9.01	ALOGPS
logP	15.57	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	1.58	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.55 Å²	ChemAxon
Rotatable Bond Count	36	ChemAxon
Refractivity	309.07 m³·mol⁻¹	ChemAxon
Polarizability	122.12 Å³	ChemAxon
Number of Rings	1	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	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-2100000892-af073e8afb21b069b7e1	2015-09-16	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0000000900-6c213e1729b19c20b0f5	2015-09-16	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-1100000920-67ca603d3c743baa7a80	2015-09-16	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-6920000032-ad310555c6c0236db241	2015-09-16	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9120000110-7dea105b922fb269fbb9	2015-09-16	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-f73e656c65f3c33fc8cf	2015-09-16	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	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

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	1	Human	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

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

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 4-deoxy-4-formamido-Œ±-L-arabinopyranosyl ditrans,octacis-undecaprenyl phosphate (MMDBc0032161)

MOL for #<Metabolite:0x000055b76e0975b0>

3D MOL for #<Metabolite:0x000055b76e0975b0>

3D SDF for #<Metabolite:0x000055b76e0975b0>

3D-SDF for #<Metabolite:0x000055b76e0975b0>

PDB for #<Metabolite:0x000055b76e0975b0>

3D PDB for #<Metabolite:0x000055b76e0975b0>

SMILES for #<Metabolite:0x000055b76e0975b0>

INCHI for #<Metabolite:0x000055b76e0975b0>

Structure for #<Metabolite:0x000055b76e0975b0>

3D Structure for #<Metabolite:0x000055b76e0975b0>