NP-MRD: Showing NP-Card for (2s)-2-(5-{[(2s)-3,3-dimethyloxiran-2-yl]methyl}-1h-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate (NP0215261)

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Record Information

Version

2.0

Created at

2022-09-05 14:49:13 UTC

Updated at

2022-09-05 14:49:13 UTC

NP-MRD ID

NP0215261

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-(5-{[(2s)-3,3-dimethyloxiran-2-yl]methyl}-1h-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate

Description

(2S)-2-(5-{[(2S)-3,3-dimethyloxiran-2-yl]methyl}-1H-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. (2s)-2-(5-{[(2s)-3,3-dimethyloxiran-2-yl]methyl}-1h-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate is found in Hexalobus crispiflorus. Based on a literature review very few articles have been published on (2S)-2-(5-{[(2S)-3,3-dimethyloxiran-2-yl]methyl}-1H-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052216492D          

 39 41  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309052216492D          

 39 41  0  0  1  0            999 V2000
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   20.7120   -4.2847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3810   -3.8019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1336   -4.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8026   -3.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5552   -3.9951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2242   -3.5123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1405   -2.6915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9768   -3.8502    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6457   -3.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3983   -3.7054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   27.0673   -3.2226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0699   -2.3976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8554   -2.1452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3382   -2.8141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1584   -2.9030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4915   -3.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0045   -4.3236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3376   -5.0784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1578   -5.1672    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   30.9126   -4.8341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8237   -5.6543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.5295   -6.0814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6637   -6.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1843   -4.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8511   -3.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4820   -4.5261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6612   -4.6098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3027   -4.4425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5656   -5.3469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 29 28  1  6  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 27 34  1  0  0  0  0
 34 35  2  0  0  0  0
 21 35  1  0  0  0  0
 24 35  1  0  0  0  0
 20 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 36 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0215261

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC(=O)OC[C@H](C1=CNC2=CC=C(C[C@@H]3OC3(C)C)C=C12)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C34H55NO4/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-32(36)38-25-29(33(2,3)37)28-24-35-30-21-20-26(22-27(28)30)23-31-34(4,5)39-31/h20-22,24,29,31,35,37H,6-19,23,25H2,1-5H3/t29-,31+/m1/s1

> <INCHI_KEY>
XAXMUUPQRQFKJI-VEEOACQBSA-N

> <FORMULA>
C34H55NO4

> <MOLECULAR_WEIGHT>
541.817

> <EXACT_MASS>
541.413109255

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
67.9050855611327

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-(5-{[(2S)-3,3-dimethyloxiran-2-yl]methyl}-1H-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate

> <JCHEM_LOGP>
8.931207539666666

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.2683383560709

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.854585228210972

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8537787719384973

> <JCHEM_POLAR_SURFACE_AREA>
74.85000000000001

> <JCHEM_REFRACTIVITY>
160.74560000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-(5-{[(2S)-3,3-dimethyloxiran-2-yl]methyl}-1H-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      25.394  -9.350   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.643  -8.449   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.048  -9.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.297  -8.178   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.702  -8.809   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      31.950  -7.908   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.355  -8.539   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      34.604  -7.638   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      36.009  -8.269   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.258  -7.367   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      38.662  -7.998   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      39.911  -7.097   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      41.316  -7.728   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      42.565  -6.827   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      43.970  -7.457   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      45.218  -6.556   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      45.062  -5.024   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      46.623  -7.187   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      47.872  -6.286   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      49.277  -6.917   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      50.526  -6.016   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      50.531  -4.476   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      51.997  -4.004   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      52.898  -5.253   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      54.429  -5.419   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      55.051  -6.828   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      54.142  -8.071   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      54.764  -9.480   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      56.295  -9.645   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      57.703  -9.024   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      57.538 -10.555   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      58.855 -11.352   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      57.239 -12.065   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      52.611  -7.905   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      51.989  -6.496   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      49.433  -8.449   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      47.901  -8.605   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      50.965  -8.293   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      49.589  -9.981   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   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   36                                                  
CONECT   21   20   22   35                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   35                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29   31                                                       
CONECT   31   30   29   32   33                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   27   35                                                       
CONECT   35   34   21   24                                                  
CONECT   36   20   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36                                                            
CONECT   39   36                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2-(5-{[(2S)-3,3-dimethyloxiran-2-yl]methyl}-1H-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoic acid	Generator

Chemical Formula

C₃₄H₅₅NO₄

Average Mass

541.8170 Da

Monoisotopic Mass

541.41311 Da

IUPAC Name

(2S)-2-(5-{[(2S)-3,3-dimethyloxiran-2-yl]methyl}-1H-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate

Traditional Name

(2S)-2-(5-{[(2S)-3,3-dimethyloxiran-2-yl]methyl}-1H-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCC(=O)OC[C@H](C1=CNC2=CC=C(C[C@@H]3OC3(C)C)C=C12)C(C)(C)O

InChI Identifier

InChI=1S/C34H55NO4/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-32(36)38-25-29(33(2,3)37)28-24-35-30-21-20-26(22-27(28)30)23-31-34(4,5)39-31/h20-22,24,29,31,35,37H,6-19,23,25H2,1-5H3/t29-,31+/m1/s1

InChI Key

XAXMUUPQRQFKJI-VEEOACQBSA-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
Hexalobus crispiflorus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Fatty acid ester
Substituted pyrrole
Fatty acyl
Benzenoid
Pyrrole
Heteroaromatic compound
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Azacycle
Organic oxygen compound
Alcohol
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	8.93	ChemAxon
pKa (Strongest Acidic)	14.85	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.85 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	160.75 m³·mol⁻¹	ChemAxon
Polarizability	67.91 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8228627

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10053067

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-(5-{[(2s)-3,3-dimethyloxiran-2-yl]methyl}-1h-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate (NP0215261)

MOL for NP0215261 ((2s)-2-(5-{[(2s)-3,3-dimethyloxiran-2-yl]methyl}-1h-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate)

3D MOL for NP0215261 ((2s)-2-(5-{[(2s)-3,3-dimethyloxiran-2-yl]methyl}-1h-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate)

3D SDF for NP0215261 ((2s)-2-(5-{[(2s)-3,3-dimethyloxiran-2-yl]methyl}-1h-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate)

3D-SDF for NP0215261 ((2s)-2-(5-{[(2s)-3,3-dimethyloxiran-2-yl]methyl}-1h-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate)

PDB for NP0215261 ((2s)-2-(5-{[(2s)-3,3-dimethyloxiran-2-yl]methyl}-1h-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate)

3D PDB for NP0215261 ((2s)-2-(5-{[(2s)-3,3-dimethyloxiran-2-yl]methyl}-1h-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate)

SMILES for NP0215261 ((2s)-2-(5-{[(2s)-3,3-dimethyloxiran-2-yl]methyl}-1h-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate)

INCHI for NP0215261 ((2s)-2-(5-{[(2s)-3,3-dimethyloxiran-2-yl]methyl}-1h-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate)

Structure for NP0215261 ((2s)-2-(5-{[(2s)-3,3-dimethyloxiran-2-yl]methyl}-1h-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate)

3D Structure for NP0215261 ((2s)-2-(5-{[(2s)-3,3-dimethyloxiran-2-yl]methyl}-1h-indol-3-yl)-3-hydroxy-3-methylbutyl hexadecanoate)