NP-MRD: Showing NP-Card for Eugeniifoline (NP0333146)

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Record Information

Version

1.0

Created at

2024-05-11 12:27:38 UTC

Updated at

2024-05-13 01:14:19 UTC

NP-MRD ID

NP0333146

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Eugeniifoline

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01232315042D          

 29 33  0  0  1  0            999 V2000
    3.2715    0.3580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3813   -0.4597    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4911   -1.2774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8379   -1.7813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0749   -1.4676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0345    0.0442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0970    0.8669    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4683    1.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8987    1.0616    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2125    1.8246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3317    0.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1443   -0.7734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7975   -0.2695    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5891   -0.5017    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9073   -1.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6704   -1.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7802   -2.2185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5432   -2.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3236   -0.8969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2541   -1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183   -0.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9651   -0.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2839   -0.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4822   -0.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0872    0.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1450    1.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9467    1.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5162    0.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3408    0.6310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  2  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
  6 12  1  1  0  0  0
  6 13  1  0  0  0  0
 13 11  1  0  0  0  0
 13 14  1  1  0  0  0
 13 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
 16 19  2  0  0  0  0
 15 20  2  0  0  0  0
  3 20  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  2  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 21 29  1  0  0  0  0
M  END


  Mrv2104 01232315042D          

 29 33  0  0  1  0            999 V2000
    3.2715    0.3580    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3813   -0.4597    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4911   -1.2774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8379   -1.7813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0749   -1.4676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0345    0.0442    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0970    0.8669    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4683    1.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8987    1.0616    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2125    1.8246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3317    0.3593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1443   -0.7734    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7975   -0.2695    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5891   -0.5017    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9073   -1.0871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6704   -1.4008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7802   -2.2185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5432   -2.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3236   -0.8969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2541   -1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6183   -0.1460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9651   -0.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2839   -0.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4822   -0.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0872    0.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1450    1.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9467    1.2041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5162    0.6072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3408    0.6310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  2  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
  6 12  1  1  0  0  0
  6 13  1  0  0  0  0
 13 11  1  0  0  0  0
 13 14  1  1  0  0  0
 13 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
 16 19  2  0  0  0  0
 15 20  2  0  0  0  0
  3 20  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  2  0  0  0  0
  5 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 23 28  1  0  0  0  0
 28 29  1  0  0  0  0
 21 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0333146

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12C[C@H](O)[C@H](C)[C@@]1([H])[C@@]1([H])N(CCC3=C1NC1=CC=CC=C31)C=C2C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C21H24N2O3/c1-11-17(24)9-14-15(21(25)26-2)10-23-8-7-13-12-5-3-4-6-16(12)22-19(13)20(23)18(11)14/h3-6,10-11,14,17-18,20,22,24H,7-9H2,1-2H3/t11-,14+,17-,18+,20+/m0/s1

> <INCHI_KEY>
LTBTXKAHUWWXQG-QWXPXUONSA-N

> <FORMULA>
C21H24N2O3

> <MOLECULAR_WEIGHT>
352.434

> <EXACT_MASS>
352.178692641

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
39.8568276227067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2R,3S,4R,5S,7S)-5-hydroxy-4-methyl-10,20-diazapentacyclo[11.7.0.0^{2,10}.0^{3,7}.0^{14,19}]icosa-1(13),8,14,16,18-pentaene-8-carboxylate

> <JCHEM_LOGP>
2.320776696999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.372813220475937

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.909397479876176

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3532853440197634

> <JCHEM_POLAR_SURFACE_AREA>
65.56

> <JCHEM_REFRACTIVITY>
99.50800000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R,3S,4R,5S,7S)-5-hydroxy-4-methyl-10,20-diazapentacyclo[11.7.0.0^{2,10}.0^{3,7}.0^{14,19}]icosa-1(13),8,14,16,18-pentaene-8-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JAN-23         0                                  
HETATM    1  H   UNK     0       6.107   0.668   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       6.312  -0.858   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       6.517  -2.384   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.297  -3.325   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.873  -2.740   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.531   0.083   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.648   1.618   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.474   2.615   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.144   1.982   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.730   3.406   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.952   0.671   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       7.736  -1.444   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       8.955  -0.503   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      10.433  -0.937   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       9.160  -2.029   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.585  -2.615   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.790  -4.141   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      12.214  -4.727   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.804  -1.674   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.941  -2.970   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.887  -0.273   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.668  -1.213   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.397  -0.344   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.900  -0.708   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.163   0.407   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.271   1.884   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.767   2.248   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.830   1.133   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       4.370   1.178   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    6   21                                             
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4   22                                                       
CONECT    6    2    7   12   13                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   13                                                       
CONECT   12    6                                                            
CONECT   13    6   11   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16   20                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16                                                            
CONECT   20   15    3                                                       
CONECT   21    2   22   29                                                  
CONECT   22   21    5   23                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23   29                                                  
CONECT   29   28   21                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄N₂O₃

Average Mass

352.4340 Da

Monoisotopic Mass

352.17869 Da

IUPAC Name

methyl (2R,3S,4R,5S,7S)-5-hydroxy-4-methyl-10,20-diazapentacyclo[11.7.0.0^{2,10}.0^{3,7}.0^{14,19}]icosa-1(13),8,14,16,18-pentaene-8-carboxylate

Traditional Name

methyl (2R,3S,4R,5S,7S)-5-hydroxy-4-methyl-10,20-diazapentacyclo[11.7.0.0^{2,10}.0^{3,7}.0^{14,19}]icosa-1(13),8,14,16,18-pentaene-8-carboxylate

CAS Registry Number

Not Available

SMILES

[H][C@]12C[C@H](O)[C@H](C)[C@@]1([H])[C@@]1([H])N(CCC3=C1NC1=CC=CC=C31)C=C2C(=O)OC

InChI Identifier

InChI=1S/C21H24N2O3/c1-11-17(24)9-14-15(21(25)26-2)10-23-8-7-13-12-5-3-4-6-16(12)22-19(13)20(23)18(11)14/h3-6,10-11,14,17-18,20,22,24H,7-9H2,1-2H3/t11-,14+,17-,18+,20+/m0/s1

InChI Key

LTBTXKAHUWWXQG-QWXPXUONSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-05-11	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-05-11	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-05-11	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-05-11	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)	yylow@um.edu.my	Not Available	Not Available	2024-05-11	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

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	2.32	ChemAxon
pKa (Strongest Acidic)	14.91	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.56 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	99.51 m³·mol⁻¹	ChemAxon
Polarizability	39.86 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, Wong SK, Yong KT, Lim KH, Lim SH, Low YY: Eugeniifoline, a Pentacyclic Indole Alkaloid from Leuconotis eugeniifolia, and Configurational Revision of Synthetic Eugeniifoline Isolated from a Diversity-Enhanced Extract. J Nat Prod. 2023 Jan 27;86(1):232-236. doi: 10.1021/acs.jnatprod.2c00731. Epub 2023 Jan 18. [PubMed:36651825 ]

Showing NP-Card for Eugeniifoline (NP0333146)

MOL for NP0333146 (Eugeniifoline)

3D MOL for NP0333146 (Eugeniifoline)

3D SDF for NP0333146 (Eugeniifoline)

3D-SDF for NP0333146 (Eugeniifoline)

PDB for NP0333146 (Eugeniifoline)

3D PDB for NP0333146 (Eugeniifoline)

SMILES for NP0333146 (Eugeniifoline)

INCHI for NP0333146 (Eugeniifoline)

Structure for NP0333146 (Eugeniifoline)

3D Structure for NP0333146 (Eugeniifoline)