NP-MRD: Showing NP-Card for Flexilin (NP0058074)

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Record Information

Version

2.0

Created at

2022-04-28 03:28:01 UTC

Updated at

2022-04-28 03:28:01 UTC

NP-MRD ID

NP0058074

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Flexilin

Description

Flexilin belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Flexilin is found in Caulerpa flexilis, Caulerpa trifaria and Udotea conglutinata. Flexilin was first documented in 1996 (PMID: 8783183). Based on a literature review very few articles have been published on Flexilin (PMID: 9278449).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 51 50  0  0  0  0  0  0  0  0999 V2000
   -6.1976    3.9088    0.4212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1822    2.8236    0.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9703    2.1344    1.4244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4524    2.5467   -0.7488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5084    1.5000   -0.6890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9010    0.2833   -0.9990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0297   -0.8923   -0.9793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5328   -2.0420   -1.3113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8605   -3.2404   -1.3508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9062   -4.2032   -0.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1579   -5.4921   -0.4250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6165   -3.9248    0.6603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6243   -0.6009   -0.5708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6909   -1.7092   -0.4989 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7177   -1.5204   -0.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3436   -0.4555    0.2760 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6727    0.8164    0.5391 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8405   -0.5207    0.5656 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5924    0.4467   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0449    0.4079   -0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7329    1.4574    0.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0183    2.7425    0.5962 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1907    1.3920    0.6098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5578    4.0602    1.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7610    4.8815    0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0241    3.5977   -0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4906    1.6988   -0.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9275    0.1661   -1.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6130   -2.0357   -1.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9113   -6.3053   -0.3852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4283   -5.6062    0.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6136   -5.5988   -1.3621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7118    0.0266    0.3218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2792    0.0759   -1.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0765   -2.3775    0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7130   -2.3811   -1.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4126   -2.4115   -0.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4689    1.5804    0.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1871    1.3084   -0.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0890    0.7256    1.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9235   -0.1837    1.6210 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2002   -1.5371    0.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3705    0.1894   -1.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2137    1.4712   -0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5748   -0.5142   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1296    2.6134    1.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6670    3.1716   -0.3429 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6981    3.4966    1.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6115    2.3663    0.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7098    0.9410   -0.2640 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3282    0.7223    1.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 23  1  0
 21 20  2  3
 20 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  1  0
 16 15  2  0
 15 14  1  0
 14 13  1  0
 13  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 22 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 23 51  1  0
 20 45  1  0
 19 43  1  0
 19 44  1  0
 18 41  1  0
 18 42  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
 15 37  1  0
 14 35  1  0
 14 36  1  0
 13 33  1  0
 13 34  1  0
  8 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
  6 28  1  0
  5 27  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
M  END


  Mrv1652304282205282D          

 23 22  0  0  0  0            999 V2000
   -0.1914    1.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059   -1.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059   -2.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -2.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -3.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349   -2.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    0.0809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    3.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    3.7934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    4.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    5.0309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    5.0309    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  2  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  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4 11  1  0  0  0  0
  1 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0058074

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(=C/OC(C)=O)\C=C\OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H28O4/c1-15(2)8-6-9-16(3)10-7-11-19(14-23-18(5)21)12-13-22-17(4)20/h8,10,12-14H,6-7,9,11H2,1-5H3/b13-12+,16-10+,19-14+

> <INCHI_KEY>
LGLHHRCOQKUINX-AUHCMFQASA-N

> <FORMULA>
C19H28O4

> <MOLECULAR_WEIGHT>
320.429

> <EXACT_MASS>
320.198759382

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.214508281947026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1E,5E)-2-[(E)-2-(acetyloxy)ethenyl]-6,10-dimethylundeca-1,5,9-trien-1-yl acetate

> <ALOGPS_LOGP>
4.98

> <JCHEM_LOGP>
3.837642061666666

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.8172799529354

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
94.43999999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1E,5E)-2-[(E)-2-(acetyloxy)ethenyl]-6,10-dimethylundeca-1,5,9-trien-1-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      -0.357   2.461   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.976   1.691   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.976   0.151   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.357  -0.619   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.357  -2.159   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.691  -2.929   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.691  -4.469   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.025  -5.239   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.025  -6.779   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.358  -4.469   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.691   0.151   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.357   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.976   4.771   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.310   4.001   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       3.644   4.771   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.644   6.311   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.977   4.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.691   4.771   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.691   6.311   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -3.025   7.081   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -3.025   8.621   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -4.358   9.391   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.691   9.391   0.000  0.00  0.00           C+0
CONECT    1    2   12                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    4                                                            
CONECT   12    1   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   12   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₈O₄

Average Mass

320.4290 Da

Monoisotopic Mass

320.19876 Da

IUPAC Name

(1E,5E)-2-[(E)-2-(acetyloxy)ethenyl]-6,10-dimethylundeca-1,5,9-trien-1-yl acetate

Traditional Name

(1E,5E)-2-[(E)-2-(acetyloxy)ethenyl]-6,10-dimethylundeca-1,5,9-trien-1-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC\C(=C/OC(C)=O)\C=C\OC(C)=O

InChI Identifier

InChI=1S/C19H28O4/c1-15(2)8-6-9-16(3)10-7-11-19(14-23-18(5)21)12-13-22-17(4)20/h8,10,12-14H,6-7,9,11H2,1-5H3/b13-12+,16-10+,19-14+

InChI Key

LGLHHRCOQKUINX-AUHCMFQASA-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
Caulerpa flexilis	Plant	KNApSAcK
Caulerpa trifaria	LOTUS Database	35616633
Udotea conglutinata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Farsesane sesquiterpenoid
Sesquiterpenoid
Dicarboxylic acid or derivatives
Enol ester
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	4.98	ALOGPS
logP	3.84	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	94.44 m³·mol⁻¹	ChemAxon
Polarizability	37.21 Å³	ChemAxon
Number of Rings	0	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

C00011386

Chemspider ID

10469916

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23424864

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Elefteriou F, Exposito JY, Garrone R, Lethias C: Characterization of the bovine tenascin-X. J Biol Chem. 1997 Sep 5;272(36):22866-74. doi: 10.1074/jbc.272.36.22866. [PubMed:9278449 ]
Lethias C, Descollonges Y, Boutillon MM, Garrone R: Flexilin: a new extracellular matrix glycoprotein localized on collagen fibrils. Matrix Biol. 1996 Apr;15(1):11-9. doi: 10.1016/s0945-053x(96)90122-5. [PubMed:8783183 ]

Showing NP-Card for Flexilin (NP0058074)

MOL for NP0058074 (Flexilin)

3D MOL for NP0058074 (Flexilin)

3D SDF for NP0058074 (Flexilin)

3D-SDF for NP0058074 (Flexilin)

PDB for NP0058074 (Flexilin)

3D PDB for NP0058074 (Flexilin)

SMILES for NP0058074 (Flexilin)

INCHI for NP0058074 (Flexilin)

Structure for NP0058074 (Flexilin)

3D Structure for NP0058074 (Flexilin)