NP-MRD: Showing NP-Card for Trilobine (NP0051033)

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Record Information

Version

2.0

Created at

2022-04-27 22:28:56 UTC

Updated at

2022-04-27 22:28:56 UTC

NP-MRD ID

NP0051033

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Trilobine

Description

Trilobine, also known as trilobine sulfate, belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed. Trilobine is found in Anisocycla cymosa, Anisocycla grandidieri, Anisocycla jollyana, Cocculus hirsutus, Cocculus laurifolius, Cocculus pendulus, Cocculus sarmentosus, Cocculus trilobus , Cryptomeria japonica, Cryptomeria japonica D.DON., Pachygone ovata, Stepania japonica, Stephania cepharantha , Stephania japonica and Stephania pierrei. Trilobine was first documented in 2021 (PMID: 33166629). Based on a literature review very few articles have been published on Trilobine (PMID: 34194523).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200282D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304282200282D          

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    6.0647   -2.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8405   -2.0817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5760   -3.6435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7835   -4.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0391   -4.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3030   -4.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1935   -3.1931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9798   -2.9138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7160   -3.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3674   -2.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7508   -1.6727    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9065   -1.4099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2624   -1.9735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4622   -2.7893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3094   -3.7497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1356   -3.9545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4528    1.6242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  4 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 10 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  1  0  0  0
 14 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  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
 22 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 29 34  1  0  0  0  0
 32 35  1  0  0  0  0
 35 36  1  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
  2 39  1  0  0  0  0
 25 40  1  0  0  0  0
 40 41  1  0  0  0  0
 19 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051033

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C[C@@H]3N(C)CCC4=CC5=C(OC6=C7[C@H](CC8=CC=C(OC1=C2)C=C8)NCCC7=CC(OC)=C6O5)C=C34

> <INCHI_IDENTIFIER>
InChI=1S/C35H34N2O5/c1-37-13-11-22-17-30-31-19-25(22)27(37)15-21-6-9-28(38-2)29(16-21)40-24-7-4-20(5-8-24)14-26-33-23(10-12-36-26)18-32(39-3)34(41-30)35(33)42-31/h4-9,16-19,26-27,36H,10-15H2,1-3H3/t26-,27-/m0/s1

> <INCHI_KEY>
XZAXGQMTBGFTFE-SVBPBHIXSA-N

> <FORMULA>
C35H34N2O5

> <MOLECULAR_WEIGHT>
562.666

> <EXACT_MASS>
562.246772203

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
62.387978094163486

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8S,21S)-13,27-dimethoxy-7-methyl-15,29,31-trioxa-7,22-diazaoctacyclo[19.9.3.2^{16,19}.1^{4,30}.1^{10,14}.0^{3,8}.0^{25,33}.0^{28,32}]heptatriaconta-1(30),2,4(34),10,12,14(37),16,18,25,27,32,35-dodecaene

> <ALOGPS_LOGP>
4.71

> <JCHEM_LOGP>
5.937598595666666

> <ALOGPS_LOGS>
-5.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.557086173407983

> <JCHEM_POLAR_SURFACE_AREA>
61.42

> <JCHEM_REFRACTIVITY>
162.07629999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.94e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8S,21S)-13,27-dimethoxy-7-methyl-15,29,31-trioxa-7,22-diazaoctacyclo[19.9.3.2^{16,19}.1^{4,30}.1^{10,14}.0^{3,8}.0^{25,33}.0^{28,32}]heptatriaconta-1(30),2,4(34),10,12,14(37),16,18,25,27,32,35-dodecaene

> <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       3.423  -6.746   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.385  -5.629   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.209  -4.359   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.674  -3.545   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.634  -4.731   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.887  -6.319   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.361  -7.923   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       5.569  -9.675   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       7.136  -4.186   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.781  -2.826   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.862  -1.618   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.288  -2.006   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.713  -0.268   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.318  -0.202   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.224  -1.473   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.340  -2.795   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.979  -1.152   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.613   0.283   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      11.666   1.480   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0      10.212   1.003   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.020  -0.607   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.701  -2.459   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.263  -2.926   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.854  -4.376   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.864  -5.563   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.321  -5.423   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.902  -3.886   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.408  -6.801   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       8.929  -7.565   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.540  -8.368   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.166  -7.591   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.961  -5.960   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.429  -5.439   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.803  -6.057   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.419  -4.739   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.268  -3.122   0.000  0.00  0.00           C+0
HETATM   37  N   UNK     0       1.692  -2.632   0.000  0.00  0.00           N+0
HETATM   38  C   UNK     0       0.490  -3.684   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.863  -5.207   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      13.644  -6.999   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      15.187  -7.382   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      12.045   3.032   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   39                                                  
CONECT    3    2    4   36                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    5   10                                                       
CONECT   10    9   11   16                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11    4                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15   20                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   10                                                       
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   42                                                  
CONECT   20   19   14   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   40                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   32   36                                                       
CONECT   36   35    3   37                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38    2                                                       
CONECT   40   25   41                                                       
CONECT   41   40                                                            
CONECT   42   19                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   98    0
END

View in JSmol

Synonyms

Value	Source
Trilobine sulfate	MeSH

Chemical Formula

C₃₅H₃₄N₂O₅

Average Mass

562.6660 Da

Monoisotopic Mass

562.24677 Da

IUPAC Name

(8S,21S)-13,27-dimethoxy-7-methyl-15,29,31-trioxa-7,22-diazaoctacyclo[19.9.3.2^{16,19}.1^{4,30}.1^{10,14}.0^{3,8}.0^{25,33}.0^{28,32}]heptatriaconta-1(30),2,4(34),10,12,14(37),16,18,25,27,32,35-dodecaene

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C[C@@H]3N(C)CCC4=CC5=C(OC6=C7[C@H](CC8=CC=C(OC1=C2)C=C8)NCCC7=CC(OC)=C6O5)C=C34

InChI Identifier

InChI=1S/C35H34N2O5/c1-37-13-11-22-17-30-31-19-25(22)27(37)15-21-6-9-28(38-2)29(16-21)40-24-7-4-20(5-8-24)14-26-33-23(10-12-36-26)18-32(39-3)34(41-30)35(33)42-31/h4-9,16-19,26-27,36H,10-15H2,1-3H3/t26-,27-/m0/s1

InChI Key

XZAXGQMTBGFTFE-SVBPBHIXSA-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
Anisocycla cymosa	Plant	KNApSAcK
Anisocycla grandidieri	Plant	KNApSAcK
Anisocycla jollyana	Plant	KNApSAcK
Cocculus hirsutus	LOTUS Database	35616633
Cocculus laurifolius	Plant	KNApSAcK
Cocculus pendulus	LOTUS Database	35616633
Cocculus sarmentosus	Plant	KNApSAcK
Cocculus trilobus	Plant	KNApSAcK
Cryptomeria japonica	LOTUS Database	35616633
Cryptomeria japonica D.DON.	Plant	KNApSAcK
Pachygone ovata	LOTUS Database	35616633
Stepania japonica	-	KNApSAcK
Stephania cephalantha	Plant	KNApSAcK
Stephania japonica	LOTUS Database	35616633
Stephania pierrei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Oxyneolignan skeleton
Dibenzo-p-dioxin
Diaryl ether
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Tertiary amine
Tertiary aliphatic amine
Azacycle
Secondary amine
Oxacycle
Ether
Secondary aliphatic amine
Organoheterocyclic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinolines (CHEBI:9723 )

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	4.71	ALOGPS
logP	5.94	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	8.56	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	61.42 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	162.08 m³·mol⁻¹	ChemAxon
Polarizability	62.39 Å³	ChemAxon
Number of Rings	8	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001926

Chemspider ID

147818

KEGG Compound ID

C09669

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

169007

PDB ID

Not Available

ChEBI ID

9723

Good Scents ID

Not Available

References

General References

Zhang H, Wang X, Guo Y, Liu X, Zhao X, Teka T, Lv C, Han L, Huang Y, Pan G: Thirteen bisbenzylisoquinoline alkaloids in five Chinese medicinal plants: Botany, traditional uses, phytochemistry, pharmacokinetic and toxicity studies. J Ethnopharmacol. 2021 Mar 25;268:113566. doi: 10.1016/j.jep.2020.113566. Epub 2020 Nov 7. [PubMed:33166629 ]
Ahmad JB, Ajani EO, Sabiu S: Chemical Group Profiling, In Vitro and In Silico Evaluation of Aristolochia ringens on alpha-Amylase and alpha-Glucosidase Activity. Evid Based Complement Alternat Med. 2021 Jun 4;2021:6679185. doi: 10.1155/2021/6679185. eCollection 2021. [PubMed:34194523 ]

Showing NP-Card for Trilobine (NP0051033)

MOL for NP0051033 (Trilobine)

3D MOL for NP0051033 (Trilobine)

3D SDF for NP0051033 (Trilobine)

3D-SDF for NP0051033 (Trilobine)

PDB for NP0051033 (Trilobine)

3D PDB for NP0051033 (Trilobine)

SMILES for NP0051033 (Trilobine)

INCHI for NP0051033 (Trilobine)

Structure for NP0051033 (Trilobine)

3D Structure for NP0051033 (Trilobine)