NP-MRD: Showing NP-Card for Eugeniinaline D (NP0332335)

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Record Information

Version

1.0

Created at

2024-01-04 12:09:34 UTC

Updated at

2024-05-05 00:33:28 UTC

NP-MRD ID

NP0332335

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eugeniinaline D

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01042412092D          

 30 34  0  0  1  0            999 V2000
    3.2301    0.8737    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5023    0.0949    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7744   -0.6840    0.0000 N   0  3  1  0  0  0  0  0  0  0  0  0
    4.0465   -1.4628    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.2360   -1.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4254   -1.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407    0.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8512    0.5662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5791    1.3450    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1234   -0.2126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9339   -0.3663    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2061   -1.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4723    0.2588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2002    1.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3896    1.1913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1175    1.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6559    2.5952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3837    3.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3069    2.1239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3955   -0.9914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5850   -0.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917    0.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1533   -0.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924   -0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6463   -0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0316    0.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0365    0.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7826    1.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4606    0.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636    0.9538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  7  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 10 20  1  1  0  0  0
 10 21  1  0  0  0  0
  3 21  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  2  0  0  0  0
  6 23  1  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
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 22 30  1  0  0  0  0
M  CHG  2   3   1   4  -1
M  END


  Mrv2104 01042412092D          

 30 34  0  0  1  0            999 V2000
    3.2301    0.8737    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5023    0.0949    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7744   -0.6840    0.0000 N   0  3  1  0  0  0  0  0  0  0  0  0
    4.0465   -1.4628    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.2360   -1.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4254   -1.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0407    0.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8512    0.5662    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.5791    1.3450    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1234   -0.2126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9339   -0.3663    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2061   -1.1451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4723    0.2588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2002    1.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3896    1.1913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1175    1.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6559    2.5952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3837    3.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3069    2.1239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3955   -0.9914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5850   -0.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917    0.2486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1533   -0.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3924   -0.0576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6463   -0.4097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0316    0.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0365    0.8826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7826    1.2347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4606    0.7646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2636    0.9538    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  7  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 10 20  1  1  0  0  0
 10 21  1  0  0  0  0
  3 21  1  0  0  0  0
  2 22  1  0  0  0  0
 22 23  2  0  0  0  0
  6 23  1  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
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 22 30  1  0  0  0  0
M  CHG  2   3   1   4  -1
M  END
> <DATABASE_ID>
NP0332335

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@@]3([H])C4=C(CC[N@@+]3([O-])C[C@@]1(O)[C@@H](C)OC[C@@H]2C(=O)OC)C1=CC=CC=C1N4

> <INCHI_IDENTIFIER>
InChI=1S/C21H26N2O5/c1-12-21(25)11-23(26)8-7-14-13-5-3-4-6-17(13)22-19(14)18(23)9-16(21)15(10-28-12)20(24)27-2/h3-6,12,15-16,18,22,25H,7-11H2,1-2H3/t12-,15+,16-,18+,21-,23-/m1/s1

> <INCHI_KEY>
FBPORFHPJQCSDR-QCOMDWLSSA-N

> <FORMULA>
C21H26N2O5

> <MOLECULAR_WEIGHT>
386.448

> <EXACT_MASS>
386.184171945

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.17051111322033

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,13R,15R,16R,19R,20R)-15-hydroxy-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraen-13-ium-13-olate

> <JCHEM_LOGP>
0.3935028199999995

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.941430879293188

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.976506672814033

> <JCHEM_PKA_STRONGEST_BASIC>
2.814799996694057

> <JCHEM_POLAR_SURFACE_AREA>
94.60999999999999

> <JCHEM_REFRACTIVITY>
103.03980000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,13R,15R,16R,19R,20R)-15-hydroxy-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraen-13-ium-13-olate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JAN-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JAN-24         0                                  
HETATM    1  H   UNK     0       6.030   1.631   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       6.538   0.177   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       7.046  -1.277   0.000  0.00  0.00           N+1
HETATM    4  O   UNK     0       7.554  -2.731   0.000  0.00  0.00           O-1
HETATM    5  C   UNK     0       6.041  -2.444   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.527  -2.157   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.543   1.344   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.056   1.057   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       8.548   2.511   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       9.564  -0.397   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.077  -0.684   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.585  -2.138   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      12.082   0.483   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.574   1.937   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.061   2.224   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.553   3.678   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.558   4.844   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      10.050   6.298   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.040   3.965   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      10.072  -1.851   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.559  -1.564   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.025   0.464   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.019  -0.703   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.599  -0.108   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.206  -0.765   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.059   0.113   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.068   1.648   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.461   2.305   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.726   1.427   0.000  0.00  0.00           C+0
HETATM   30  N   UNK     0       4.225   1.780   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    7   22                                             
CONECT    3    2    4    5   21                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5   23                                                       
CONECT    7    2    8                                                       
CONECT    8    7    9   10   15                                             
CONECT    9    8                                                            
CONECT   10    8   11   20   21                                             
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    8   16                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16                                                            
CONECT   20   10                                                            
CONECT   21   10    3                                                       
CONECT   22    2   23   30                                                  
CONECT   23   22    6   24                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24   30                                                  
CONECT   30   29   22                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   68    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₆N₂O₅

Average Mass

386.4480 Da

Monoisotopic Mass

386.18417 Da

IUPAC Name

(1S,13R,15R,16R,19R,20R)-15-hydroxy-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraen-13-ium-13-olate

Traditional Name

(1S,13R,15R,16R,19R,20R)-15-hydroxy-19-(methoxycarbonyl)-16-methyl-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraen-13-ium-13-olate

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@@]3([H])C4=C(CC[N@@+]3([O-])C[C@@]1(O)[C@@H](C)OC[C@@H]2C(=O)OC)C1=CC=CC=C1N4

InChI Identifier

InChI=1S/C21H26N2O5/c1-12-21(25)11-23(26)8-7-14-13-5-3-4-6-17(13)22-19(14)18(23)9-16(21)15(10-28-12)20(24)27-2/h3-6,12,15-16,18,22,25H,7-11H2,1-2H3/t12-,15+,16-,18+,21-,23-/m1/s1

InChI Key

FBPORFHPJQCSDR-QCOMDWLSSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-05-03	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-05-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-05-03	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-05-03	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-01-04	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-01-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-01-04	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-01-04	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-01-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-01-04	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-01-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.13300065 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.13300065 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.917898807 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.13300065 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.917898807 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.13300065, CDCl₃, simulated)	Yylow	Department of Chemistry, Faculty of Science, Universiti Malaya	Yun-Yee Low	2024-05-03	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
eugeniifolia		Not Available

Chemical Taxonomy

Classification

Not classified

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	0.39	ChemAxon
pKa (Strongest Acidic)	11.98	ChemAxon
pKa (Strongest Basic)	2.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	94.61 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	103.04 m³·mol⁻¹	ChemAxon
Polarizability	40.17 Å³	ChemAxon
Number of Rings	5	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

Not Available

References

General References

Tan YS, Ng MP, Tan CH, Tang WK, Sim KS, Yong KT, Krishnan P, Lim KH, Lim SH, Low YY: Quinoline, Indole, and Isogranatanine Alkaloids from Malayan Leuconotis eugeniifolia. J Nat Prod. 2024 Feb 23;87(2):286-296. doi: 10.1021/acs.jnatprod.3c00960. Epub 2024 Jan 29. [PubMed:38284153 ]

Showing NP-Card for Eugeniinaline D (NP0332335)

MOL for NP0332335 (Eugeniinaline D)

3D MOL for NP0332335 (Eugeniinaline D)

3D SDF for NP0332335 (Eugeniinaline D)

3D-SDF for NP0332335 (Eugeniinaline D)

PDB for NP0332335 (Eugeniinaline D)

3D PDB for NP0332335 (Eugeniinaline D)

SMILES for NP0332335 (Eugeniinaline D)

INCHI for NP0332335 (Eugeniinaline D)

Structure for NP0332335 (Eugeniinaline D)

3D Structure for NP0332335 (Eugeniinaline D)