NP-MRD: Showing NP-Card for Acroamine A3 (NP0333649)

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Record Information

Version

2.0

Created at

2024-07-31 21:16:03 UTC

Updated at

2024-11-01 00:35:20 UTC

NP-MRD ID

NP0333649

Natural Product DOI

https://doi.org/10.57994/3128

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Acroamine A3

Description

Acroamine A3 belongs to the class of organic compounds known as imidazopyrimidines. These are organic polycyclic compounds containing an imidazole ring fused to a pyrimidine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions. Based on a literature review very few articles have been published on Acroamine A3.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 04142323492D          

 22 24  0  0  0  0            999 V2000
    4.0668    2.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2089   -1.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226   -2.5975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3157   -2.7691    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0199   -3.5227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0968   -2.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4552   -1.4415    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    0.2837   -0.6345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
  4 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 15 19  1  0  0  0  0
 19 20  1  0  0  0  0
 16 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  CHG  1  13   1
M  END
> <DATABASE_ID>
NP0333649

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C=C(CCNC2=NC(=N)N(C)C3=C2N(C)C=N3)[N+](C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H21N8/c1-19-7-10(21(3)9-19)5-6-16-12-11-13(17-8-20(11)2)22(4)14(15)18-12/h7-9H,5-6H2,1-4H3,(H2,15,16,18)/q+1

> <INCHI_KEY>
OAJQHEIWFOKQBJ-UHFFFAOYSA-N

> <FORMULA>
C14H21N8

> <MOLECULAR_WEIGHT>
301.377

> <EXACT_MASS>
301.188369128

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.42129642908813

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{2-[(2-imino-3,7-dimethyl-3,7-dihydro-2H-purin-6-yl)amino]ethyl}-1,3-dimethyl-1H-imidazol-3-ium

> <JCHEM_LOGP>
-4.503506289471746

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.2295080838378

> <JCHEM_PKA_STRONGEST_BASIC>
8.41054080089763

> <JCHEM_POLAR_SURFACE_AREA>
78.11

> <JCHEM_REFRACTIVITY>
97.3132

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
5-{2-[(2-imino-3,7-dimethylpurin-6-yl)amino]ethyl}-1,3-dimethylimidazol-1-ium

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-APR-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-APR-23         0                                  
HETATM    1  N   UNK     0       7.591   4.383   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       6.258   2.073   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       4.924  -0.237   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       3.590  -1.007   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590  -2.547   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.257  -3.317   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.096  -4.849   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       0.589  -5.169   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      -0.037  -6.576   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.181  -3.835   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       0.850  -2.691   0.000  0.00  0.00           N+1
HETATM   14  C   UNK     0       0.530  -1.184   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       4.924   4.383   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       4.924   5.923   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    8   14                                                  
CONECT   14   13                                                            
CONECT   15    4   16   19                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   15   20                                                  
CONECT   20   19                                                            
CONECT   21   16    2   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₂₁N₈

Average Mass

301.3770 Da

Monoisotopic Mass

301.18837 Da

IUPAC Name

4-{2-[(2-imino-3,7-dimethyl-3,7-dihydro-2H-purin-6-yl)amino]ethyl}-1,3-dimethyl-1H-imidazol-3-ium

Traditional Name

5-{2-[(2-imino-3,7-dimethylpurin-6-yl)amino]ethyl}-1,3-dimethylimidazol-1-ium

CAS Registry Number

Not Available

SMILES

CN1C=C(CCNC2=NC(=N)N(C)C3=C2N(C)C=N3)[N+](C)=C1

InChI Identifier

InChI=1S/C14H21N8/c1-19-7-10(21(3)9-19)5-6-16-12-11-13(17-8-20(11)2)22(4)14(15)18-12/h7-9H,5-6H2,1-4H3,(H2,15,16,18)/q+1

InChI Key

OAJQHEIWFOKQBJ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	dayani.sarathparakumge@nih.gov	National Cancer Institute	Dayani Sarath Parakumge	2024-07-31	View Spectrum
HMBC NMR	[¹H, ¹⁵N] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	dayani.sarathparakumge@nih.gov	National Cancer Institute	Dayani Sarath Parakumge	2024-07-31	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	dayani.sarathparakumge@nih.gov	National Cancer Institute	Dayani Sarath Parakumge	2024-07-31	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	dayani.sarathparakumge@nih.gov	National Cancer Institute	Dayani Sarath Parakumge	2024-07-31	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	dayani.sarathparakumge@nih.gov	National Cancer Institute	Dayani Sarath Parakumge	2024-07-31	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	dayani.sarathparakumge@nih.gov	National Cancer Institute	Dayani Sarath Parakumge	2024-07-31	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	dayani.sarathparakumge@nih.gov	National Cancer Institute	Dayani Sarath Parakumge	2024-07-31	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	dayani.sarathparakumge@nih.gov	National Cancer Institute	Dayani Sarath Parakumge	2024-07-31	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.314502325, CD₃OD, simulated)	dayani.sarathparakumge@nih.gov	National Cancer Institute	Dayani Sarath Parakumge	2024-07-31	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as imidazopyrimidines. These are organic polycyclic compounds containing an imidazole ring fused to a pyrimidine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Not Available

Direct Parent

Imidazopyrimidines

Alternative Parents

Substituents

Imidazopyrimidine
Secondary aliphatic/aromatic amine
Imidolactam
Pyrimidine
N-substituted imidazole
1,2-dihydropyrimidine
Hydropyrimidine
Heteroaromatic compound
Azole
Formamidine
Azacycle
Carboximidamide
Secondary amine
Amidine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Imine
Amine
Organic cation
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	-4.5	ChemAxon
pKa (Strongest Acidic)	19.23	ChemAxon
pKa (Strongest Basic)	8.41	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	78.11 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.31 m³·mol⁻¹	ChemAxon
Polarizability	33.42 Å³	ChemAxon
Number of Rings	3	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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Acroamine A3 (NP0333649)

MOL for NP0333649 (Acroamine A3)

3D MOL for NP0333649 (Acroamine A3)

3D SDF for NP0333649 (Acroamine A3)

3D-SDF for NP0333649 (Acroamine A3)

PDB for NP0333649 (Acroamine A3)

3D PDB for NP0333649 (Acroamine A3)

SMILES for NP0333649 (Acroamine A3)

INCHI for NP0333649 (Acroamine A3)

Structure for NP0333649 (Acroamine A3)

3D Structure for NP0333649 (Acroamine A3)