NP-MRD: Showing NP-Card for Isotenulin (NP0051918)

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Record Information

Version

2.0

Created at

2022-04-27 23:07:16 UTC

Updated at

2022-04-27 23:07:16 UTC

NP-MRD ID

NP0051918

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Isotenulin

Description

(3R,3aR,4R,4aR,7aS,8R,9aS)-3,4a,8-trimethyl-2,5-dioxo-2H,3H,3aH,4H,4aH,5H,7aH,8H,9H,9aH-azuleno[6,5-b]furan-4-yl acetate belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids containing a lactone ring. Isotenulin is found in Helenium arizonicum and Helenium bigelovii. Based on a literature review very few articles have been published on (3R,3aR,4R,4aR,7aS,8R,9aS)-3,4a,8-trimethyl-2,5-dioxo-2H,3H,3aH,4H,4aH,5H,7aH,8H,9H,9aH-azuleno[6,5-b]furan-4-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 44 46  0  0  0  0  0  0  0  0999 V2000
    2.7652    3.2075    0.3395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6768    2.3067    0.7901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1655    2.4675    1.9119 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.3052   -0.0347 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1983    0.3843    0.3027 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8393   -0.9327    0.4626 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0137   -2.1340    0.0927 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1628   -2.1966    0.9786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2361   -1.2831    0.4968 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7730   -0.3956    1.6021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9321   -0.4934   -0.7352 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1603    0.2855   -1.0583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9673    1.5639   -0.9270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5887    1.8050   -0.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1234    2.8934   -0.0759 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8784    0.5143   -0.6757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2357    0.6157   -2.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -3.1636    0.3602 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1527   -2.6733   -0.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1209   -3.4012   -0.5319 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0680   -1.1935   -0.3743 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2942   -0.4911    0.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8925    3.1205   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7270    2.9612    0.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4446    4.2557    0.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1659    0.6974    1.3041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1609   -1.0833    1.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1876   -2.2329   -0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5343   -3.2399    1.1697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8628   -1.8311    2.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1104   -1.9485    0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5604    0.6680    1.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8435   -0.5705    1.8288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2322   -0.6804    2.5526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7966   -1.1759   -1.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0880   -0.2194   -1.3649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7204    2.3237   -1.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8966    1.2400   -2.7368 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7651    1.0712   -2.0187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2290   -0.3882   -2.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8945   -0.9644   -1.4467 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1835   -1.1702    0.1136 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5267    0.4004   -0.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1669   -0.2242    1.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  6
 16  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  7 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  5  6  1  0
 16 11  1  0
 22 42  1  0
 22 43  1  0
 22 44  1  0
 21 41  1  6
  6 27  1  1
  7 28  1  6
  8 29  1  0
  8 30  1  0
  9 31  1  6
 10 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  6
 12 36  1  0
 13 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
  5 26  1  1
  1 23  1  0
  1 24  1  0
  1 25  1  0
M  END


  Mrv1652304282201072D          

 22 24  0  0  1  0            999 V2000
    3.4890    2.3296    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3054    1.5253    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5621    1.1673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8188    1.5253    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6352    2.3296    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1496    2.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9746    2.9746    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3326    3.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8136    2.4036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4893    1.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3150    1.4614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1106    1.1022    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0366    0.2805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621    0.3423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8476   -0.0702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0272   -0.1564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8476   -0.8952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0136    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0876    0.2805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6349    1.6449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3107    2.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2684    0.7011    0.0000 C   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  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  1  0  0  0
  5  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  1  0  0  0
  3 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
  1 21  1  1  0  0  0
  2 22  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0051918

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H]2[C@H](C[C@@H](C)[C@H]3C=CC(=O)[C@@]3(C)[C@@H]2OC(C)=O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h5-6,8-9,11-12,14-15H,7H2,1-4H3/t8-,9-,11-,12+,14-,15-,17+/m1/s1

> <INCHI_KEY>
NEIIKBWBBCJSQU-XKRFYNIESA-N

> <FORMULA>
C17H22O5

> <MOLECULAR_WEIGHT>
306.358

> <EXACT_MASS>
306.146723808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
31.532296834958565

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,3aR,4R,4aR,7aS,8R,9aS)-3,4a,8-trimethyl-2,5-dioxo-2H,3H,3aH,4H,4aH,5H,7aH,8H,9H,9aH-azuleno[6,5-b]furan-4-yl acetate

> <ALOGPS_LOGP>
1.64

> <JCHEM_LOGP>
2.1463776273333335

> <ALOGPS_LOGS>
-2.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.95411942661456

> <JCHEM_PKA_STRONGEST_BASIC>
-5.106732424358491

> <JCHEM_POLAR_SURFACE_AREA>
69.67

> <JCHEM_REFRACTIVITY>
78.97120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aR,4R,4aR,7aS,8R,9aS)-3,4a,8-trimethyl-2,5-dioxo-3H,3aH,4H,7aH,8H,9H,9aH-azuleno[6,5-b]furan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       6.513   4.349   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.170   2.847   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.783   2.179   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.395   2.847   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.052   4.349   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.013   5.553   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.553   5.553   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.221   6.940   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.519   4.487   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.913   3.071   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.588   2.728   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.073   2.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.935   0.524   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.783   0.639   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.449  -0.131   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.917  -0.292   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.449  -1.671   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.492   2.057   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.630   0.524   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.652   3.071   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.047   4.487   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.101   1.309   0.000  0.00  0.00           C+0
CONECT    1    2    7   21                                                  
CONECT    2    1    3   18   22                                             
CONECT    3    2    4   14                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    4   13                                                  
CONECT   13   12                                                            
CONECT   14    3   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    2   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20    1                                                       
CONECT   22    2                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
(3R,3AR,4R,4ar,7as,8R,9as)-3,4a,8-trimethyl-2,5-dioxo-2H,3H,3ah,4H,4ah,5H,7ah,8H,9H,9ah-azuleno[6,5-b]furan-4-yl acetic acid	Generator

Chemical Formula

C₁₇H₂₂O₅

Average Mass

306.3580 Da

Monoisotopic Mass

306.14672 Da

IUPAC Name

(3R,3aR,4R,4aR,7aS,8R,9aS)-3,4a,8-trimethyl-2,5-dioxo-2H,3H,3aH,4H,4aH,5H,7aH,8H,9H,9aH-azuleno[6,5-b]furan-4-yl acetate

Traditional Name

(3R,3aR,4R,4aR,7aS,8R,9aS)-3,4a,8-trimethyl-2,5-dioxo-3H,3aH,4H,7aH,8H,9H,9aH-azuleno[6,5-b]furan-4-yl acetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H]2[C@H](C[C@@H](C)[C@H]3C=CC(=O)[C@@]3(C)[C@@H]2OC(C)=O)OC1=O

InChI Identifier

InChI=1S/C17H22O5/c1-8-7-12-14(9(2)16(20)22-12)15(21-10(3)18)17(4)11(8)5-6-13(17)19/h5-6,8-9,11-12,14-15H,7H2,1-4H3/t8-,9-,11-,12+,14-,15-,17+/m1/s1

InChI Key

NEIIKBWBBCJSQU-XKRFYNIESA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Helenium arizonicum	Plant	KNApSAcK
Helenium bigelovii	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpene lactones. These are sesquiterpenoids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Sesquiterpene lactones

Alternative Parents

Substituents

Helenalin-skeleton
Ambrosanolide
Pseudoguaiane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.64	ALOGPS
logP	2.15	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	16.95	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.97 m³·mol⁻¹	ChemAxon
Polarizability	31.53 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

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

162933389

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Isotenulin (NP0051918)

MOL for NP0051918 (Isotenulin)

3D MOL for NP0051918 (Isotenulin)

3D SDF for NP0051918 (Isotenulin)

3D-SDF for NP0051918 (Isotenulin)

PDB for NP0051918 (Isotenulin)

3D PDB for NP0051918 (Isotenulin)

SMILES for NP0051918 (Isotenulin)

INCHI for NP0051918 (Isotenulin)

Structure for NP0051918 (Isotenulin)

3D Structure for NP0051918 (Isotenulin)