NP-MRD: Showing NP-Card for Makaluvamine E (NP0076828)

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Record Information

Version

2.0

Created at

2022-04-28 22:01:03 UTC

Updated at

2022-04-28 22:01:03 UTC

NP-MRD ID

NP0076828

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Makaluvamine E

Description

Makaluvamine E belongs to the class of organic compounds known as pyrrolo[4,3,2-de]quinolines. These are organic heterocyclic compounds with a structure based on the Pyrrolo[4,3,2-de]quinoline skeleton. Makaluvamine E is found in Zyzzya fuliginosa and Zyzzya sp.. Based on a literature review very few articles have been published on Makaluvamine E.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 44  0  0  0  0  0  0  0  0999 V2000
   -4.8436   -2.8662   -0.6986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4114   -1.5263   -0.3957 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2282   -0.4888   -0.0817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4456    0.6635    0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1706    0.2314   -0.0450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1390   -1.0955   -0.3767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8024   -1.6541   -0.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7181   -2.8684   -0.9154 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6094   -0.8201   -0.4833 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6689   -1.3661   -0.7075 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8540   -0.8502   -0.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0066   -0.7820   -0.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2348   -0.2714   -0.1469 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3956   -0.2371   -0.8892 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5804    0.2545   -0.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6068    0.7124    0.9603 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7779    1.2120    1.5467 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4559    0.6829    1.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2782    0.1889    1.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6898    0.4835   -0.1538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0097    1.0963    0.0898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2025    2.3217    0.4076 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4927    2.9013    0.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7027    2.0533    0.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2256   -2.8794   -1.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6713   -3.1936   -0.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0474   -3.6055   -0.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3034   -0.4661   -0.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8055   -2.1830   -1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7678   -0.5223    0.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9699   -1.1517   -1.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4541   -0.5784   -1.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4879    0.2844   -0.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9991    2.1926    1.4799 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4687    1.0447    2.7390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4276    0.2020    1.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1726    1.1101   -0.0578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4800    3.3017    1.7150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5765    3.8441    0.0182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2678    2.1094    1.5008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3747    2.5158   -0.2818 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 24  1  0
 24 23  1  0
 23 22  1  0
 22 21  2  0
 21 20  1  0
 20  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
  9  7  1  0
  7  8  2  0
  7  6  1  0
  6  5  2  0
  6  2  1  0
  5  4  1  0
  5 21  1  0
 19 13  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
 24 40  1  0
 24 41  1  0
 23 38  1  0
 23 39  1  0
 20 37  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 19 36  1  0
M  END


  Mrv1652304292200012D          

 24 27  0  0  0  0            999 V2000
   -0.5821   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4959   -1.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2578   -1.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9252   -1.1425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8390   -0.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0853    0.0135    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7651    0.0135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326   -0.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3463   -1.2919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0138   -1.7768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5926   -1.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3377   -2.4121    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5127   -2.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8226   -3.0795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1862   -0.1359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8537   -0.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6073   -0.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2748   -0.7701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0285   -0.4346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6959   -0.9195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6097   -1.7400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8560   -2.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1885   -1.5906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2771   -2.2249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  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
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  4 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 13  2  0  0  0  0
 12 14  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 21 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0076828

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=C2CCN=C3C=C(N\C=C\C4=CC=C(O)C=C4)C(=O)C1=C23

> <INCHI_IDENTIFIER>
InChI=1S/C19H17N3O2/c1-22-11-13-7-9-20-15-10-16(19(24)18(22)17(13)15)21-8-6-12-2-4-14(23)5-3-12/h2-6,8,10-11,21,23H,7,9H2,1H3/b8-6+

> <INCHI_KEY>
SRIGKAHCWXJXIV-SOFGYWHQSA-N

> <FORMULA>
C19H17N3O2

> <MOLECULAR_WEIGHT>
319.364

> <EXACT_MASS>
319.132076799

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
35.295580955501016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-{[(E)-2-(4-hydroxyphenyl)ethenyl]amino}-2-methyl-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,7,9-tetraen-11-one

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
1.6927096361750849

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.158114258298427

> <JCHEM_PKA_STRONGEST_BASIC>
8.380171337859657

> <JCHEM_POLAR_SURFACE_AREA>
66.62

> <JCHEM_REFRACTIVITY>
95.8207

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-{[(E)-2-(4-hydroxyphenyl)ethenyl]amino}-2-methyl-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,7,9-tetraen-11-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  C   UNK     0      -1.087  -0.880   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.926  -2.412   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.481  -3.038   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.727  -2.133   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.566  -0.601   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.159   0.025   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       3.295   0.025   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.541  -0.880   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.380  -2.412   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.626  -3.317   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.973  -3.038   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.497  -4.503   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.957  -4.503   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.402  -5.748   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       5.948  -0.254   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       7.194  -1.159   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.600  -0.532   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.846  -1.438   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.253  -0.811   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.499  -1.716   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.338  -3.248   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.931  -3.874   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.685  -2.969   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.584  -4.153   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    4   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12    3                                                       
CONECT   14   12                                                            
CONECT   15    8   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   21                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₇N₃O₂

Average Mass

319.3640 Da

Monoisotopic Mass

319.13208 Da

IUPAC Name

10-{[(E)-2-(4-hydroxyphenyl)ethenyl]amino}-2-methyl-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,7,9-tetraen-11-one

Traditional Name

10-{[(E)-2-(4-hydroxyphenyl)ethenyl]amino}-2-methyl-2,7-diazatricyclo[6.3.1.0^{4,12}]dodeca-1(12),3,7,9-tetraen-11-one

CAS Registry Number

Not Available

SMILES

CN1C=C2CCN=C3C=C(N\C=C\C4=CC=C(O)C=C4)C(=O)C1=C23

InChI Identifier

InChI=1S/C19H17N3O2/c1-22-11-13-7-9-20-15-10-16(19(24)18(22)17(13)15)21-8-6-12-2-4-14(23)5-3-12/h2-6,8,10-11,21,23H,7,9H2,1H3/b8-6+

InChI Key

SRIGKAHCWXJXIV-SOFGYWHQSA-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
Zyzzya fuliginosa	-	KNApSAcK
Zyzzya sp.	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrrolo[4,3,2-de]quinolines. These are organic heterocyclic compounds with a structure based on the Pyrrolo[4,3,2-de]quinoline skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Pyrroloquinolines

Direct Parent

Pyrrolo[4,3,2-de]quinolines

Alternative Parents

Substituents

Pyrrolo[4,3,2-de]quinoline
Indole or derivatives
Aryl ketone
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
N-methylpyrrole
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Ketimine
Ketone
Azacycle
Enamine
Secondary aliphatic amine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Amine
Organic oxygen compound
Imine
Organic nitrogen 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	2.68	ALOGPS
logP	1.69	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.16	ChemAxon
pKa (Strongest Basic)	8.38	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.62 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.82 m³·mol⁻¹	ChemAxon
Polarizability	35.3 Å³	ChemAxon
Number of Rings	4	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

C00039713

Chemspider ID

8148823

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9973231

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Makaluvamine E (NP0076828)

MOL for NP0076828 (Makaluvamine E)

3D MOL for NP0076828 (Makaluvamine E)

3D SDF for NP0076828 (Makaluvamine E)

3D-SDF for NP0076828 (Makaluvamine E)

PDB for NP0076828 (Makaluvamine E)

3D PDB for NP0076828 (Makaluvamine E)

SMILES for NP0076828 (Makaluvamine E)

INCHI for NP0076828 (Makaluvamine E)

Structure for NP0076828 (Makaluvamine E)

3D Structure for NP0076828 (Makaluvamine E)