NP-MRD: Showing NP-Card for n,n,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0²,⁶]trideca-1(13),2(6),4,7,9-pentaen-4-amine (NP0175347)

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Record Information

Version

2.0

Created at

2022-09-03 12:46:58 UTC

Updated at

2022-09-03 12:46:59 UTC

NP-MRD ID

NP0175347

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n,n,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0²,⁶]trideca-1(13),2(6),4,7,9-pentaen-4-amine

Description

Paragracine belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group. n,n,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0²,⁶]trideca-1(13),2(6),4,7,9-pentaen-4-amine is found in Antipathes dichotoma, Axinella damicornis and Hydrozoanthus gracilis. Based on a literature review very few articles have been published on Paragracine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -2.7982    3.7306    0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4737    2.4340    0.3909 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7767    1.3542    0.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4272    1.3378    0.1969 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9807    0.0742    0.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3478   -0.2648    0.0330 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3474    0.6277   -0.0242 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4760   -0.0907   -0.1537 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7547    0.4983   -0.2104 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1982    1.1841   -1.3868 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077    0.3877    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1738   -1.4240   -0.1771 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8446   -1.5603   -0.0598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1536   -2.7710   -0.0242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1662   -3.0081    0.3200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2169   -2.1172    0.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5851   -2.6898    0.3782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1807   -0.7405    0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2316    0.0867    0.4049 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3695    4.3274   -0.4429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7595    3.6094   -0.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7834    4.2495    1.2615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2874    1.6692    0.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3029    1.3604   -1.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7098    2.2013   -1.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8815    0.6704   -2.3212 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5696   -0.1149    0.7364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1123   -0.2112    1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8171    1.3694    1.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7022   -3.6455   -0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4619   -3.9970    0.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9627   -2.5334    1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6280   -3.7281    0.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2347   -2.0939   -0.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2498   -0.1819    0.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3 19  1  0
 19 18  1  0
 18 16  2  0
 16 17  1  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13  6  2  0
  6  7  1  0
  7  8  1  0
  8 12  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  5 18  1  0
 12 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 19 35  1  0
 17 32  1  0
 17 33  1  0
 17 34  1  0
 15 31  1  0
 14 30  1  0
  7 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
M  END


  Mrv1652309032214462D          

 19 21  0  0  0  0            999 V2000
   -0.7882   -0.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0202   -0.0242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6248   -0.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -0.3191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8746   -1.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6996   -1.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1541   -0.3191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9493   -0.5386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5944   -0.0242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4714    0.7916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3623   -0.3256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9864   -1.3627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2140   -1.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0304   -2.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2871   -2.8149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5438   -2.4569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8988   -2.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3602   -1.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5878   -1.3627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  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
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  8 12  2  0  0  0  0
 12 13  1  0  0  0  0
  6 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
  3 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0175347

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN=C1NC2=C(C)C=CC3=C(NC(=N3)N(C)C)C2=N1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N6/c1-7-5-6-8-10(18-13(15-8)19(3)4)11-9(7)16-12(14-2)17-11/h5-6H,1-4H3,(H,15,18)(H,14,16,17)

> <INCHI_KEY>
CXHKQUKWIWQJDW-UHFFFAOYSA-N

> <FORMULA>
C13H16N6

> <MOLECULAR_WEIGHT>
256.313

> <EXACT_MASS>
256.143644539

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.833477659798938

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N,N,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0^{2,6}]trideca-1(13),2(6),4,7,9-pentaen-4-amine

> <ALOGPS_LOGP>
1.34

> <JCHEM_LOGP>
1.109630724

> <ALOGPS_LOGS>
-2.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.485791823345668

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.44467751848998

> <JCHEM_PKA_STRONGEST_BASIC>
4.387415856443927

> <JCHEM_POLAR_SURFACE_AREA>
68.67

> <JCHEM_REFRACTIVITY>
77.56299999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N,N,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0^{2,6}]trideca-1(13),2(6),4,7,9-pentaen-4-amine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.471  -0.608   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.038  -0.045   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       1.166  -1.005   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       2.651  -0.596   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.499  -1.881   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.039  -1.881   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       5.888  -0.596   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.372  -1.005   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       8.576  -0.045   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       8.347   1.478   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.010  -0.608   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       7.441  -2.544   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.999  -3.085   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.657  -4.586   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.269  -5.254   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.882  -4.586   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.678  -5.546   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.539  -3.085   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       1.097  -2.544   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    5   19                                                  
CONECT   19   18    3                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
2-(Dimethylamino)-8-(methylamino)-6-methyl-1,3,7,9-tetraazacyclopent(e)azulene	MeSH

Chemical Formula

C₁₃H₁₆N₆

Average Mass

256.3130 Da

Monoisotopic Mass

256.14364 Da

IUPAC Name

N,N,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0^{2,6}]trideca-1(13),2(6),4,7,9-pentaen-4-amine

Traditional Name

N,N,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0^{2,6}]trideca-1(13),2(6),4,7,9-pentaen-4-amine

CAS Registry Number

Not Available

SMILES

CN=C1NC2=C(C)C=CC3=C(NC(=N3)N(C)C)C2=N1

InChI Identifier

InChI=1S/C13H16N6/c1-7-5-6-8-10(18-13(15-8)19(3)4)11-9(7)16-12(14-2)17-11/h5-6H,1-4H3,(H,15,18)(H,14,16,17)

InChI Key

CXHKQUKWIWQJDW-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Antipathes dichotoma	LOTUS Database	35616633
Axinella damicornis	LOTUS Database	35616633
Hydrozoanthus gracilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Dialkylarylamines

Alternative Parents

Substituents

Dialkylarylamine
Secondary aliphatic/aromatic amine
Aminoimidazole
Heteroaromatic compound
Imidazole
Azole
Azacycle
Organoheterocyclic compound
Secondary amine
Organopnictogen compound
Hydrocarbon derivative
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	1.34	ALOGPS
logP	1.11	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	11.44	ChemAxon
pKa (Strongest Basic)	4.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.67 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	77.56 m³·mol⁻¹	ChemAxon
Polarizability	28.83 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

Not Available

Chemspider ID

90647

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100309

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n,n,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0²,⁶]trideca-1(13),2(6),4,7,9-pentaen-4-amine (NP0175347)

MOL for NP0175347 (n,n,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0²,⁶]trideca-1(13),2(6),4,7,9-pentaen-4-amine)

3D MOL for NP0175347 (n,n,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0²,⁶]trideca-1(13),2(6),4,7,9-pentaen-4-amine)

3D SDF for NP0175347 (n,n,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0²,⁶]trideca-1(13),2(6),4,7,9-pentaen-4-amine)

3D-SDF for NP0175347 (n,n,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0²,⁶]trideca-1(13),2(6),4,7,9-pentaen-4-amine)

PDB for NP0175347 (n,n,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0²,⁶]trideca-1(13),2(6),4,7,9-pentaen-4-amine)

3D PDB for NP0175347 (n,n,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0²,⁶]trideca-1(13),2(6),4,7,9-pentaen-4-amine)

SMILES for NP0175347 (n,n,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0²,⁶]trideca-1(13),2(6),4,7,9-pentaen-4-amine)

INCHI for NP0175347 (n,n,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0²,⁶]trideca-1(13),2(6),4,7,9-pentaen-4-amine)

Structure for NP0175347 (n,n,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0²,⁶]trideca-1(13),2(6),4,7,9-pentaen-4-amine)

3D Structure for NP0175347 (n,n,9-trimethyl-12-(methylimino)-3,5,11,13-tetraazatricyclo[8.3.0.0²,⁶]trideca-1(13),2(6),4,7,9-pentaen-4-amine)