NP-MRD: Showing NP-Card for Hydroxylunidine (NP0083553)

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Record Information

Version

2.0

Created at

2022-04-29 04:33:44 UTC

Updated at

2022-04-29 04:33:44 UTC

NP-MRD ID

NP0083553

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Hydroxylunidine

Description

UNII-R46F0GPF77 belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group. Hydroxylunidine is found in Lunasia amara, Lunasia amara var. repanda and Ptelea trifoliata . Based on a literature review very few articles have been published on UNII-R46F0GPF77.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 45 47  0  0  0  0  0  0  0  0999 V2000
   -0.1758   -3.3680   -0.3077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0052   -2.3509    0.6224 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5621   -1.1201    0.4084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2269   -0.0566    0.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6430   -0.3191   -0.1619 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5561    0.8171   -0.3904 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5723    1.7549    0.6645 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9723    0.2804   -0.4871 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4667   -0.3333    0.7863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9443    1.3920   -0.8675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0630   -0.6678   -1.5163 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3970    1.1636   -0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3078    2.1288   -0.5465 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7164    1.3485   -0.0174 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3353    2.6515   -0.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4710    0.3122    0.3646 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8269    0.4839    0.5437 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6614   -0.5391    0.9343 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1132   -1.8033    1.1588 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7557   -1.9680    0.9783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9147   -0.9386    0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9449   -0.0420    1.0208 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9909    1.1417    0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6431    1.6040    0.3991 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5306   -3.3502   -1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2030   -3.3580   -0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1149   -4.3532    0.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0054   -0.8604    0.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855   -1.0432   -0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3869    1.3372   -1.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4348    1.2455    1.4912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2799    0.3912    1.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9801   -1.2935    1.0152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5590   -0.4911    0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9486    0.9381   -0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9300    2.2046   -0.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6553    1.7468   -1.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0261   -0.7958   -1.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7806    2.9809    0.7362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0828    2.5903   -1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5578    3.3995   -0.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7558   -2.6221    1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3508   -2.9490    1.1550 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1283    0.8403   -0.8061 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7233    1.8704    0.6067 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
  8 11  1  6
  4 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 24  1  0
 24 23  1  0
 23 22  1  0
 22 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21  3  1  0
 21 16  1  0
 18 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  6
  7 31  1  0
  9 32  1  0
  9 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 23 44  1  0
 23 45  1  0
 19 42  1  0
 20 43  1  0
M  END


  Mrv1652304292206332D          

 24 26  0  0  1  0            999 V2000
    0.5597    0.5775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9943   -0.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8189   -0.0980    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2089    0.6290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2535   -0.7992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0781   -0.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108   -0.1434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3745   -0.4553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3140   -1.2781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5127   -1.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228   -2.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2982   -2.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636   -1.5262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0390   -1.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6490   -2.2790    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1756   -2.3048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -0.8508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2203   -0.8765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6549   -0.1753    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2649    0.5517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4795   -0.2010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3041   -0.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5052    0.6236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4537   -1.0256    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  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  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
  6 10  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
 12 13  2  0  0  0  0
  5 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
 14 17  2  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0083553

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C[C@H](O)C(C)(C)O)C(=O)N(C)C2=C3OCOC3=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C17H21NO6/c1-17(2,21)12(19)7-10-14(22-4)9-5-6-11-15(24-8-23-11)13(9)18(3)16(10)20/h5-6,12,19,21H,7-8H2,1-4H3/t12-/m0/s1

> <INCHI_KEY>
DAWBKOMKNXDZAN-LBPRGKRZSA-N

> <FORMULA>
C17H21NO6

> <MOLECULAR_WEIGHT>
335.356

> <EXACT_MASS>
335.1368874

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.67459701256591

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-[(2S)-2,3-dihydroxy-3-methylbutyl]-6-methoxy-9-methyl-2H,8H,9H-[1,3]dioxolo[4,5-h]quinolin-8-one

> <ALOGPS_LOGP>
0.94

> <JCHEM_LOGP>
-0.0860203430000002

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.287560069971356

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.778696685068205

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8060373526023733

> <JCHEM_POLAR_SURFACE_AREA>
88.46000000000001

> <JCHEM_REFRACTIVITY>
86.71179999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-[(2S)-2,3-dihydroxy-3-methylbutyl]-6-methoxy-9-methyl-2H-[1,3]dioxolo[4,5-h]quinolin-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       1.045   1.078   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.856  -0.231   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       3.395  -0.183   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.123   1.174   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.207  -1.492   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.746  -1.444   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.740  -0.268   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.166  -0.850   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.053  -2.386   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.557  -2.753   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.829  -4.110   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.290  -4.158   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.479  -2.849   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.939  -2.897   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.211  -4.254   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.328  -4.302   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.128  -1.588   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.411  -1.636   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.222  -0.327   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.494   1.030   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.762  -0.375   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.301  -0.423   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.810   1.164   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -2.714  -1.915   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13                                                  
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    6    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5   14                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
CONECT   17   14    2   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23   24                                             
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   21                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₂₁NO₆

Average Mass

335.3560 Da

Monoisotopic Mass

335.13689 Da

IUPAC Name

7-[(2S)-2,3-dihydroxy-3-methylbutyl]-6-methoxy-9-methyl-2H,8H,9H-[1,3]dioxolo[4,5-h]quinolin-8-one

Traditional Name

7-[(2S)-2,3-dihydroxy-3-methylbutyl]-6-methoxy-9-methyl-2H-[1,3]dioxolo[4,5-h]quinolin-8-one

CAS Registry Number

Not Available

SMILES

COC1=C(C[C@H](O)C(C)(C)O)C(=O)N(C)C2=C3OCOC3=CC=C12

InChI Identifier

InChI=1S/C17H21NO6/c1-17(2,21)12(19)7-10-14(22-4)9-5-6-11-15(24-8-23-11)13(9)18(3)16(10)20/h5-6,12,19,21H,7-8H2,1-4H3/t12-/m0/s1

InChI Key

DAWBKOMKNXDZAN-LBPRGKRZSA-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
Lunasia amara	Plant	KNApSAcK
Lunasia amara var. repanda	Plant	KNApSAcK
Ptelea trifoliata	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroquinolones. Hydroquinolones are compounds containing a hydrogenated quinoline bearing a ketone group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Quinolones and derivatives

Direct Parent

Hydroquinolones

Alternative Parents

Substituents

Dihydroquinolone
Dihydroquinoline
Benzodioxole
Alkyl aryl ether
Pyridinone
Pyridine
Benzenoid
Heteroaromatic compound
Vinylogous ester
Tertiary alcohol
1,2-diol
Lactam
Secondary alcohol
Acetal
Ether
Oxacycle
Azacycle
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Alcohol
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
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	0.94	ALOGPS
logP	-0.086	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	13.78	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	88.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	86.71 m³·mol⁻¹	ChemAxon
Polarizability	34.67 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

C00052318

Chemspider ID

58828514

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101219830

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Hydroxylunidine (NP0083553)

MOL for NP0083553 (Hydroxylunidine)

3D MOL for NP0083553 (Hydroxylunidine)

3D SDF for NP0083553 (Hydroxylunidine)

3D-SDF for NP0083553 (Hydroxylunidine)

PDB for NP0083553 (Hydroxylunidine)

3D PDB for NP0083553 (Hydroxylunidine)

SMILES for NP0083553 (Hydroxylunidine)

INCHI for NP0083553 (Hydroxylunidine)

Structure for NP0083553 (Hydroxylunidine)

3D Structure for NP0083553 (Hydroxylunidine)