NP-MRD: Showing NP-Card for Aniquinazoline B (NP0011961)

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Record Information

Version

1.0

Created at

2021-01-05 21:29:09 UTC

Updated at

2021-07-15 17:10:27 UTC

NP-MRD ID

NP0011961

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Aniquinazoline B

Provided By

NPAtlas

Description

(2R,5S)-2-{2-hydroxy-1-[(1R,4R)-3-hydroxy-1-methyl-6-oxo-1H,4H,6H-pyrazino[2,1-b]quinazolin-4-yl]propan-2-yl}-3-phenyl-5-(propan-2-yl)imidazolidin-4-one belongs to the class of organic compounds known as phenylimidazolidines. These are polycyclic compounds containing an imidazoline substituted by a phenyl group. Aniquinazoline B is found in Aspergillus. It was first documented in 2013 (PMID: 23880937). Based on a literature review a significant number of articles have been published on (2R,5S)-2-{2-hydroxy-1-[(1R,4R)-3-hydroxy-1-methyl-6-oxo-1H,4H,6H-pyrazino[2,1-b]quinazolin-4-yl]propan-2-yl}-3-phenyl-5-(propan-2-yl)imidazolidin-4-one (PMID: 34424657) (PMID: 34424656) (PMID: 34424655) (PMID: 34424654) (PMID: 34424653) (PMID: 34424652).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117003D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242117003D          

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M  END
> <DATABASE_ID>
NP0011961

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@](C([H])([H])[H])(C([H])([H])[C@@]1([H])N2C(=O)C3=C([H])C([H])=C([H])C([H])=C3N=C2[C@]([H])(N([H])C1=O)C([H])([H])[H])[C@]1([H])N([H])[C@]([H])(C(=O)N1C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H31N5O4/c1-15(2)21-25(35)31(17-10-6-5-7-11-17)26(30-21)27(4,36)14-20-23(33)28-16(3)22-29-19-13-9-8-12-18(19)24(34)32(20)22/h5-13,15-16,20-21,26,30,36H,14H2,1-4H3,(H,28,33)/t16-,20-,21+,26-,27-/m1/s1

> <INCHI_KEY>
PZCYVUJYVOAEFM-MJKJVAEFSA-N

> <FORMULA>
C27H31N5O4

> <MOLECULAR_WEIGHT>
489.576

> <EXACT_MASS>
489.237604498

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.06374727066401

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,4R)-4-[(2R)-2-hydroxy-2-[(2R,4S)-5-oxo-1-phenyl-4-(propan-2-yl)imidazolidin-2-yl]propyl]-1-methyl-1H,2H,3H,4H,6H-pyrazino[2,1-b]quinazoline-3,6-dione

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
2.1066447956666665

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.995069057336675

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.424533013108253

> <JCHEM_PKA_STRONGEST_BASIC>
5.4161182977977305

> <JCHEM_POLAR_SURFACE_AREA>
114.33999999999997

> <JCHEM_REFRACTIVITY>
134.69660000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4R)-4-[(2R)-2-hydroxy-2-[(2R,4S)-4-isopropyl-5-oxo-1-phenylimidazolidin-2-yl]propyl]-1-methyl-1H,2H,4H-pyrazino[2,1-b]quinazoline-3,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

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 34 67  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -5.349  -2.676  -0.314  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.787  -1.308  -0.632  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.045  -0.374   0.507  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.328  -1.396  -1.031  0.00  0.00           C+0
HETATM    5  N   UNK     0      -2.503  -1.951  -0.017  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.712  -0.913   0.584  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.208  -1.240   0.459  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.001  -2.471   1.265  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.493  -0.189   1.071  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.151  -1.285  -0.973  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.551  -1.571  -1.351  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.986  -2.898  -0.884  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.398  -3.908  -1.366  0.00  0.00           O+0
HETATM   14  N   UNK     0       3.004  -3.111   0.054  0.00  0.00           N+0
HETATM   15  C   UNK     0       3.950  -2.067   0.307  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.347  -1.968   1.759  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.570  -0.763  -0.280  0.00  0.00           C+0
HETATM   18  N   UNK     0       4.416   0.263  -0.010  0.00  0.00           N+0
HETATM   19  C   UNK     0       4.237   1.511  -0.467  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.090   2.563  -0.194  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.839   3.824  -0.695  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.736   4.096  -1.487  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.894   3.035  -1.752  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.138   1.771  -1.253  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.290   0.696  -1.511  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.292   0.995  -2.244  0.00  0.00           O+0
HETATM   27  N   UNK     0       2.504  -0.535  -1.034  0.00  0.00           N+0
HETATM   28  N   UNK     0      -2.078   0.301  -0.065  0.00  0.00           N+0
HETATM   29  C   UNK     0      -1.876   1.647   0.314  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.121   2.038   1.611  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.934   3.365   2.010  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.498   4.308   1.107  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.250   3.928  -0.193  0.00  0.00           C+0
HETATM   34  C   UNK     0      -1.441   2.612  -0.568  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.741  -0.058  -1.269  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.808   0.645  -2.332  0.00  0.00           O+0
HETATM   37  H   UNK     0      -4.673  -3.459  -0.726  0.00  0.00           H+0
HETATM   38  H   UNK     0      -6.398  -2.777  -0.702  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.437  -2.773   0.791  0.00  0.00           H+0
HETATM   40  H   UNK     0      -5.395  -0.939  -1.509  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.475   0.586   0.133  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.852  -0.824   1.142  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.166  -0.204   1.158  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.300  -1.936  -1.994  0.00  0.00           H+0
HETATM   45  H   UNK     0      -3.141  -2.318   0.745  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.885  -0.792   1.677  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.968  -2.491   1.810  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.241  -3.422   0.748  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.757  -2.448   2.115  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.358   0.673   0.648  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.303  -0.397  -1.464  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.457  -2.146  -1.423  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.564  -1.638  -2.482  0.00  0.00           H+0
HETATM   54  H   UNK     0       3.106  -4.003   0.582  0.00  0.00           H+0
HETATM   55  H   UNK     0       4.893  -2.372  -0.240  0.00  0.00           H+0
HETATM   56  H   UNK     0       3.849  -1.146   2.286  0.00  0.00           H+0
HETATM   57  H   UNK     0       5.446  -1.813   1.881  0.00  0.00           H+0
HETATM   58  H   UNK     0       4.135  -2.963   2.237  0.00  0.00           H+0
HETATM   59  H   UNK     0       5.944   2.339   0.423  0.00  0.00           H+0
HETATM   60  H   UNK     0       5.516   4.651  -0.476  0.00  0.00           H+0
HETATM   61  H   UNK     0       3.583   5.097  -1.855  0.00  0.00           H+0
HETATM   62  H   UNK     0       2.010   3.216  -2.376  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.464   1.338   2.357  0.00  0.00           H+0
HETATM   64  H   UNK     0      -2.118   3.701   3.021  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.354   5.351   1.433  0.00  0.00           H+0
HETATM   66  H   UNK     0      -0.911   4.688  -0.879  0.00  0.00           H+0
HETATM   67  H   UNK     0      -1.250   2.304  -1.591  0.00  0.00           H+0
CONECT    1    2   37   38   39                                             
CONECT    2    1    3    4   40                                             
CONECT    3    2   41   42   43                                             
CONECT    4    2    5   35   44                                             
CONECT    5    4    6   45                                                  
CONECT    6    5    7   28   46                                             
CONECT    7    6    8    9   10                                             
CONECT    8    7   47   48   49                                             
CONECT    9    7   50                                                       
CONECT   10    7   11   51   52                                             
CONECT   11   10   12   27   53                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   54                                                  
CONECT   15   14   16   17   55                                             
CONECT   16   15   56   57   58                                             
CONECT   17   15   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21   59                                                  
CONECT   21   20   22   60                                                  
CONECT   22   21   23   61                                                  
CONECT   23   22   24   62                                                  
CONECT   24   23   25   19                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   11   17                                                  
CONECT   28    6   29   35                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31   63                                                  
CONECT   31   30   32   64                                                  
CONECT   32   31   33   65                                                  
CONECT   33   32   34   66                                                  
CONECT   34   33   29   67                                                  
CONECT   35   28   36    4                                                  
CONECT   36   35                                                            
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    2                                                            
CONECT   41    3                                                            
CONECT   42    3                                                            
CONECT   43    3                                                            
CONECT   44    4                                                            
CONECT   45    5                                                            
CONECT   46    6                                                            
CONECT   47    8                                                            
CONECT   48    8                                                            
CONECT   49    8                                                            
CONECT   50    9                                                            
CONECT   51   10                                                            
CONECT   52   10                                                            
CONECT   53   11                                                            
CONECT   54   14                                                            
CONECT   55   15                                                            
CONECT   56   16                                                            
CONECT   57   16                                                            
CONECT   58   16                                                            
CONECT   59   20                                                            
CONECT   60   21                                                            
CONECT   61   22                                                            
CONECT   62   23                                                            
CONECT   63   30                                                            
CONECT   64   31                                                            
CONECT   65   32                                                            
CONECT   66   33                                                            
CONECT   67   34                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  142    0
END

RDKit          3D

67 71  0  0  0  0  0  0  0  0999 V2000
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 34 67  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₇H₃₁N₅O₄

Average Mass

489.5760 Da

Monoisotopic Mass

489.23760 Da

IUPAC Name

(1R,4R)-4-[(2R)-2-hydroxy-2-[(2R,4S)-5-oxo-1-phenyl-4-(propan-2-yl)imidazolidin-2-yl]propyl]-1-methyl-1H,2H,3H,4H,6H-pyrazino[2,1-b]quinazoline-3,6-dione

Traditional Name

(1R,4R)-4-[(2R)-2-hydroxy-2-[(2R,4S)-4-isopropyl-5-oxo-1-phenylimidazolidin-2-yl]propyl]-1-methyl-1H,2H,4H-pyrazino[2,1-b]quinazoline-3,6-dione

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1N[C@H](N(C1=O)C1=CC=CC=C1)C(C)(O)C[C@H]1N2C(=O)C3=CC=CC=C3N=C2[C@@H](C)NC1=O

InChI Identifier

InChI=1S/C27H31N5O4/c1-15(2)21-25(35)31(17-10-6-5-7-11-17)26(30-21)27(4,36)14-20-23(33)28-16(3)22-29-19-13-9-8-12-18(19)24(34)32(20)22/h5-13,15-16,20-21,26,30,36H,14H2,1-4H3,(H,28,33)/t16-,20-,21+,26-,27?/m1/s1

InChI Key

PZCYVUJYVOAEFM-MJKJVAEFSA-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
Aspergillus	NPAtlas	23880937

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylimidazolidines. These are polycyclic compounds containing an imidazoline substituted by a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azolidines

Sub Class

Imidazolidines

Direct Parent

Phenylimidazolidines

Alternative Parents

Substituents

Phenylimidazolidine
Diazanaphthalene
Quinazoline
Alpha-amino acid or derivatives
Pyrimidone
Benzenoid
Pyrimidine
Imidazolidinone
Monocyclic benzene moiety
Heteroaromatic compound
Cyclic carboximidic acid
Tertiary carboxylic acid amide
Tertiary alcohol
Lactam
Carboxamide group
Amino acid or derivatives
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Secondary aliphatic amine
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
Alcohol
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	1.26	ALOGPS
logP	2.11	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.42	ChemAxon
pKa (Strongest Basic)	5.42	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.34 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	134.7 m³·mol⁻¹	ChemAxon
Polarizability	51.06 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA009504

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78441086

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139585730

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

An CY, Li XM, Li CS, Wang MH, Xu GM, Wang BG: Aniquinazolines A-D, four new quinazolinone alkaloids from marine-derived endophytic fungus Aspergillus nidulans. Mar Drugs. 2013 Jul 23;11(7):2682-94. doi: 10.3390/md11072682. [PubMed:23880937 ]
Puebla DL, Farrow RA: Ultrasound Guided Arthrocentesis. 2021 Jan. [PubMed:34424657 ]
Le DT, Shah S: Greater Trochanteric Bursitis Injection. 2021 Jan. [PubMed:34424656 ]
Gurnani B, Kaur K: Ocular Surface Squamous Neoplasia. 2021 Jan. [PubMed:34424655 ]
Regier BA, Rondeau B: Anesthetic Neurotoxicity. 2021 Jan. [PubMed:34424654 ]
Khalid N, Singh A: Cannabis Versus Opioids For Pain. 2021 Jan. [PubMed:34424653 ]
Ahmed FW, Majeed MS, Kirresh O: Non-diabetic Hypoglycemia. 2021 Jan. [PubMed:34424652 ]
Muranova A, Shanina E: Stiff Person Syndrome. 2021 Jan. [PubMed:34424651 ]
Ladd M, Jones EB: Texas Human Trafficking. 2021 Jan. [PubMed:34424650 ]

Showing NP-Card for Aniquinazoline B (NP0011961)

MOL for NP0011961 (Aniquinazoline B)

3D MOL for NP0011961 (Aniquinazoline B)

3D SDF for NP0011961 (Aniquinazoline B)

3D-SDF for NP0011961 (Aniquinazoline B)

PDB for NP0011961 (Aniquinazoline B)

3D PDB for NP0011961 (Aniquinazoline B)

SMILES for NP0011961 (Aniquinazoline B)

INCHI for NP0011961 (Aniquinazoline B)

Structure for NP0011961 (Aniquinazoline B)

3D Structure for NP0011961 (Aniquinazoline B)