NP-MRD: Showing NP-Card for mycolactone (NP0291097)

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Record Information

Version

2.0

Created at

2022-09-09 22:03:46 UTC

Updated at

2022-09-09 22:03:47 UTC

NP-MRD ID

NP0291097

Secondary Accession Numbers

None

Natural Product Identification

Common Name

mycolactone

Description

Mycolactone belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. mycolactone is found in Mycobacterium ulcerans. mycolactone was first documented in 2021 (PMID: 35154073). Based on a literature review a significant number of articles have been published on Mycolactone (PMID: 35939511) (PMID: 35917367) (PMID: 35889312) (PMID: 35889292) (PMID: 35401531) (PMID: 35100311).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309102200032D          

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M  END

     RDKit          3D

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M  END

  Mrv1652309102200032D          

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   -0.0000   -1.6500    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  4  0  0  0
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  5  6  1  4  0  0  0
  6  7  1  0  0  0  0
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  8  9  1  4  0  0  0
  9 10  1  0  0  0  0
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 17  2  1  4  0  0  0
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 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
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 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
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 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
 38 39  1  4  0  0  0
 39 40  1  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  1  0  0  0  0
 44 46  1  0  0  0  0
 32 47  1  0  0  0  0
 48 47  1  4  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
 25 52  1  0  0  0  0
 52 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0291097

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)CC(O)C(C)C=C(C)CC(C)C1CC=C(C)CC(C)C(CCCC(=O)O1)OC(=O)C=CC(C)=CC(C)=CC=CC(C)=CC(O)C(O)CC(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C44H70O9/c1-28(13-11-14-29(2)25-39(48)40(49)27-37(10)46)21-30(3)18-20-44(51)52-41-15-12-16-43(50)53-42(19-17-31(4)22-34(41)7)35(8)24-32(5)23-33(6)38(47)26-36(9)45/h11,13-14,17-18,20-21,23,25,33-42,45-49H,12,15-16,19,22,24,26-27H2,1-10H3

> <INCHI_KEY>
WKTLNJXZVDLRTJ-UHFFFAOYSA-N

> <FORMULA>
C44H70O9

> <MOLECULAR_WEIGHT>
743.035

> <EXACT_MASS>
742.501983834

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
123

> <JCHEM_AVERAGE_POLARIZABILITY>
86.07522435006743

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
12-(7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl)-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl 12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate

> <JCHEM_LOGP>
6.4509314039999985

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.580888609254803

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.584436646260283

> <JCHEM_PKA_STRONGEST_BASIC>
-2.545385313567307

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
219.49580000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
mycolactone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.336   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -12.003   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -14.670   0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0     -14.670  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0     -16.004   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0     -16.004   3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0     -17.338   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -18.672   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -20.005   0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0     -18.672   3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.000  -1.540   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      13.337   1.540   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      13.337  -0.000   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0      14.670   2.310   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      16.004   1.540   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      16.004  -0.000   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    2   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   52                                                  
CONECT   26   25   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   47                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38   40   41                                                  
CONECT   40   39                                                            
CONECT   41   39   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   45   46                                                  
CONECT   45   44                                                            
CONECT   46   44                                                            
CONECT   47   32   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52                                                       
CONECT   52   51   25   53                                                  
CONECT   53   52                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  106    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₄H₇₀O₉

Average Mass

743.0350 Da

Monoisotopic Mass

742.50198 Da

IUPAC Name

12-(7,9-dihydroxy-4,6-dimethyldec-4-en-2-yl)-7,9-dimethyl-2-oxo-1-oxacyclododec-9-en-6-yl 12,13,15-trihydroxy-4,6,10-trimethylhexadeca-2,4,6,8,10-pentaenoate

Traditional Name

mycolactone

CAS Registry Number

Not Available

SMILES

CC(O)CC(O)C(C)C=C(C)CC(C)C1CC=C(C)CC(C)C(CCCC(=O)O1)OC(=O)C=CC(C)=CC(C)=CC=CC(C)=CC(O)C(O)CC(C)O

InChI Identifier

InChI=1S/C44H70O9/c1-28(13-11-14-29(2)25-39(48)40(49)27-37(10)46)21-30(3)18-20-44(51)52-41-15-12-16-43(50)53-42(19-17-31(4)22-34(41)7)35(8)24-32(5)23-33(6)38(47)26-36(9)45/h11,13-14,17-18,20-21,23,25,33-42,45-49H,12,15-16,19,22,24,26-27H2,1-10H3

InChI Key

WKTLNJXZVDLRTJ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mycobacterium ulcerans	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Long chain fatty alcohol
Macrolide
Fatty alcohol
Fatty acid ester
Fatty acyl
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Lactone
Polyol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	6.45	ChemAxon
pKa (Strongest Acidic)	13.58	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	219.5 m³·mol⁻¹	ChemAxon
Polarizability	86.08 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

External Links

HMDB ID

HMDB0254969

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Mycolactone

METLIN ID

Not Available

PubChem Compound

74053234

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kawashima A, Kiriya M, En J, Tanigawa K, Nakamura Y, Fujiwara Y, Luo Y, Maruyama K, Watanabe S, Goto M, Suzuki K: Genome-wide screening identified SEC61A1 as an essential factor for mycolactone-dependent apoptosis in human premonocytic THP-1 cells. PLoS Negl Trop Dis. 2022 Aug 8;16(8):e0010672. doi: 10.1371/journal.pntd.0010672. eCollection 2022 Aug. [PubMed:35939511 ]
Amewu RK, Akolgo GA, Asare ME, Abdulai Z, Ablordey AS, Asiedu K: Evaluation of the fluorescent-thin layer chromatography (f-TLC) for the diagnosis of Buruli ulcer disease in Ghana. PLoS One. 2022 Aug 2;17(8):e0270235. doi: 10.1371/journal.pone.0270235. eCollection 2022. [PubMed:35917367 ]
Suleiman N, Yaya A, Wilson MD, Aryee S, Kwofie SK: Density Functional Theory-Based Studies Predict Carbon Nanotubes as Effective Mycolactone Inhibitors. Molecules. 2022 Jul 11;27(14):4440. doi: 10.3390/molecules27144440. [PubMed:35889312 ]
O'Keefe S, Bhadra P, Duah KB, Zong G, Tenay L, Andrews L, Schneider H, Anderson A, Hu Z, Aljewari HS, Hall BS, Simmonds RE, Helms V, High S, Shi WQ: Synthesis, Biological Evaluation and Docking Studies of Ring-Opened Analogues of Ipomoeassin F. Molecules. 2022 Jul 10;27(14):4419. doi: 10.3390/molecules27144419. [PubMed:35889292 ]
Strong E, Hart B, Wang J, Orozco MG, Lee S: Induced Synthesis of Mycolactone Restores the Pathogenesis of Mycobacterium ulcerans In Vitro and In Vivo. Front Immunol. 2022 Mar 24;13:750643. doi: 10.3389/fimmu.2022.750643. eCollection 2022. [PubMed:35401531 ]
Hall BS, Hsieh LT, Sacre S, Simmonds RE: The One That Got Away: How Macrophage-Derived IL-1beta Escapes the Mycolactone-Dependent Sec61 Blockade in Buruli Ulcer. Front Immunol. 2022 Jan 26;12:788146. doi: 10.3389/fimmu.2021.788146. eCollection 2021. [PubMed:35154073 ]
Hsieh LT, Dos Santos SJ, Hall BS, Ogbechi J, Loglo AD, Salguero FJ, Ruf MT, Pluschke G, Simmonds RE: Aberrant stromal tissue factor localisation and mycolactone-driven vascular dysfunction, exacerbated by IL-1beta, are linked to fibrin formation in Buruli ulcer lesions. PLoS Pathog. 2022 Jan 31;18(1):e1010280. doi: 10.1371/journal.ppat.1010280. eCollection 2022 Jan. [PubMed:35100311 ]
Domenger A, Choisy C, Baron L, Mayau V, Perthame E, Deriano L, Arnulf B, Bories JC, Dadaglio G, Demangel C: The Sec61 translocon is a therapeutic vulnerability in multiple myeloma. EMBO Mol Med. 2022 Mar 7;14(3):e14740. doi: 10.15252/emmm.202114740. Epub 2022 Jan 11. [PubMed:35014767 ]
Bhadra P, Dos Santos S, Gamayun I, Pick T, Neumann C, Ogbechi J, Hall BS, Zimmermann R, Helms V, Simmonds RE, Cavalie A: Mycolactone enhances the Ca2+ leak from endoplasmic reticulum by trapping Sec61 translocons in a Ca2+ permeable state. Biochem J. 2021 Nov 26;478(22):4005-4024. doi: 10.1042/BCJ20210345. [PubMed:34726690 ]
LOTUS database [Link]

Showing NP-Card for mycolactone (NP0291097)

MOL for NP0291097 (mycolactone)

3D MOL for NP0291097 (mycolactone)

3D SDF for NP0291097 (mycolactone)

3D-SDF for NP0291097 (mycolactone)

PDB for NP0291097 (mycolactone)

3D PDB for NP0291097 (mycolactone)

SMILES for NP0291097 (mycolactone)

INCHI for NP0291097 (mycolactone)

Structure for NP0291097 (mycolactone)

3D Structure for NP0291097 (mycolactone)