NP-MRD: Showing NP-Card for Hygrophylline (NP0140342)

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Record Information

Version

2.0

Created at

2022-06-29 21:27:04 UTC

Updated at

2022-06-29 21:27:04 UTC

NP-MRD ID

NP0140342

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hygrophylline

Description

Hygrophylline belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Hygrophylline was first documented in 1965 (PMID: 5891855). Based on a literature review very few articles have been published on Hygrophylline.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    1.9395    4.4485   -0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2703    3.0187   -0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3753    2.0681   -0.5321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0361    2.4031   -0.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3830    3.5404   -0.4620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5861    1.5650    0.7972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4539    0.5868    0.9899 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7570    1.1621    1.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7877    0.9670    0.5147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1703    0.3048   -0.6164 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0234   -0.7902   -0.9953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3087   -2.0741   -0.7313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3054   -1.6560    0.3490 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1553   -2.6329    0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1960   -2.3500    1.2226 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1652   -2.3644    1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8919   -3.0363    1.9153 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8812   -1.6034    0.0555 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2447   -2.2404   -0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2240   -1.6665   -1.1652 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0304   -0.1450    0.4224 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4608    0.0236    0.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8067    0.6720   -0.7963 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9892    0.6661   -1.5326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9296   -0.2724   -0.1370 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8743    5.0513   -0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3157    4.8744   -1.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4767    4.6106    0.4642 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2586    2.7699   -1.1614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0786   -0.1272    1.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6498    2.2759    1.7256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0093    0.7432    2.5425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6292    0.3649    0.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2498    1.9049    0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3517   -0.6966   -2.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9783   -0.8059   -0.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0021   -2.8550   -0.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7834   -2.3743   -1.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8026   -1.6592    1.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8236   -2.6900   -0.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5792   -3.6500    0.4971 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8619   -2.2519    0.7602 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8141   -1.7601   -0.9597 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0950   -3.3064   -0.4399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6244   -2.2886   -1.8057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3884    0.1331    1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4945    1.1015    1.2949 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2099   -0.1225    0.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5808   -0.5668    1.8661 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0460    0.2100   -1.4945 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8446    0.9242   -2.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2062   -0.4042   -0.9652 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3 23  1  0
 23 24  1  0
 23 21  1  0
 21 22  1  0
 21 18  1  0
 18 19  1  0
 18 20  1  6
 18 16  1  0
 16 17  2  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  4  1  0
  4  5  2  0
  7 25  1  0
  4  3  1  0
 25 13  1  0
 25 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
 23 50  1  6
 24 51  1  0
 21 46  1  1
 22 47  1  0
 22 48  1  0
 22 49  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 14 40  1  0
 14 41  1  0
 13 39  1  1
 12 37  1  0
 12 38  1  0
 11 35  1  0
 11 36  1  0
  9 33  1  0
  9 34  1  0
  8 31  1  0
  8 32  1  0
  7 30  1  1
 25 52  1  6
M  END


  Mrv1652306292223272D          

 25 27  0  0  0  0            999 V2000
    5.3780    3.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9824    2.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7982    2.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4026    1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2184    0.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8228    0.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6386   -0.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2430   -1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8501   -0.9135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2458   -0.3520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4572   -0.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9619   -1.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1814   -0.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1943   -0.1622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8529   -0.0330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370    0.7712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2152    1.1725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7199    0.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8255    1.0138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0097    1.8180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4053    2.3796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4051    0.7177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6329   -0.0227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4299    0.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1911    1.7416    0.0000 O   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  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
  7  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
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 14 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  2  0  0  0  0
  6 22  1  0  0  0  0
  6 23  1  0  0  0  0
  5 24  1  0  0  0  0
  4 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140342

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C1\C(O)C(C)C(C)(O)C(=O)OCC2CCN3CCC(OC1=O)C23

> <INCHI_IDENTIFIER>
InChI=1S/C18H27NO6/c1-4-12-15(20)10(2)18(3,23)17(22)24-9-11-5-7-19-8-6-13(14(11)19)25-16(12)21/h4,10-11,13-15,20,23H,5-9H2,1-3H3/b12-4-

> <INCHI_KEY>
FAFYHPIEFKLDSP-QCDXTXTGSA-N

> <FORMULA>
C18H27NO6

> <MOLECULAR_WEIGHT>
353.415

> <EXACT_MASS>
353.183837593

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
36.74392303860646

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4Z)-4-ethylidene-5,7-dihydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadecane-3,8-dione

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
0.5119758336666675

> <ALOGPS_LOGS>
-1.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.07207253180555

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.281710062712714

> <JCHEM_PKA_STRONGEST_BASIC>
8.99148492669832

> <JCHEM_POLAR_SURFACE_AREA>
96.3

> <JCHEM_REFRACTIVITY>
90.25949999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.73e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4Z)-4-ethylidene-5,7-dihydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.0^{14,17}]heptadecane-3,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0      10.039   6.396   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.167   5.348   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.823   3.846   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.951   2.798   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.608   1.297   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.736   0.249   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.392  -1.252   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      13.520  -2.301   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      10.920  -1.705   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       9.792  -0.657   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.320  -1.110   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.396  -2.341   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.939  -1.843   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       5.963  -0.303   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       7.192  -0.062   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.536   1.440   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.002   2.189   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.077   0.957   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.008   1.892   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.351   3.394   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.223   4.442   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      13.823   1.340   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.248  -0.042   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.136   0.844   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      13.423   3.251   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   25                                                  
CONECT    5    4    6   24                                                  
CONECT    6    5    7   22   23                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   11   16                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17   14                                                       
CONECT   19   16   20                                                       
CONECT   20   19    3   21                                                  
CONECT   21   20                                                            
CONECT   22    6                                                            
CONECT   23    6                                                            
CONECT   24    5                                                            
CONECT   25    4                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₇NO₆

Average Mass

353.4150 Da

Monoisotopic Mass

353.18384 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C1\C(O)C(C)C(C)(O)C(=O)OCC2CCN3CCC(OC1=O)C23

InChI Identifier

InChI=1S/C18H27NO6/c1-4-12-15(20)10(2)18(3,23)17(22)24-9-11-5-7-19-8-6-13(14(11)19)25-16(12)21/h4,10-11,13-15,20,23H,5-9H2,1-3H3/b12-4-

InChI Key

FAFYHPIEFKLDSP-QCDXTXTGSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Pyrrolizidine
Dicarboxylic acid or derivatives
N-alkylpyrrolidine
Pyrrolidine
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Lactone
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid derivative
Oxacycle
Azacycle
Organoheterocyclic compound
Alcohol
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
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

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

28504553

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6449975

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Schlosser FD, Warren FL: The Senecio alkaloids. 18. The structure of hygrophylline, the alkaloid from Senecio hygrophylus Dyer and Sm. J Chem Soc Perkin 1. 1965 Oct:5707-10. doi: 10.1039/jr9650005707. [PubMed:5891855 ]

Showing NP-Card for Hygrophylline (NP0140342)

MOL for NP0140342 (Hygrophylline)

3D MOL for NP0140342 (Hygrophylline)

3D SDF for NP0140342 (Hygrophylline)

3D-SDF for NP0140342 (Hygrophylline)

PDB for NP0140342 (Hygrophylline)

3D PDB for NP0140342 (Hygrophylline)

SMILES for NP0140342 (Hygrophylline)

INCHI for NP0140342 (Hygrophylline)

Structure for NP0140342 (Hygrophylline)

3D Structure for NP0140342 (Hygrophylline)