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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:32:23 UTC

Update Date

2023-02-21 17:19:13 UTC

HMDB ID

HMDB0029748

Secondary Accession Numbers

HMDB29748

Metabolite Identification

Common Name

2-Aminodipyrido[1,2-a:3',2'-d]imidazole

Description

2-Aminodipyrido[1,2-a:3',2'-d]imidazole, also known as glu-p-2 or imidazo[1,2-a:5,4-b']dipyridin-2-amine, belongs to the class of organic compounds known as imidazopyridines. These are organic polycyclic compounds containing an imidazole ring fused to a pyridine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center. 2-Aminodipyrido[1,2-a:3',2'-d]imidazole is a strong basic compound (based on its pKa). 2-Aminodipyrido[1,2-a:3',2'-d]imidazole is a potentially toxic compound. Parent compound of a group of potent mutagens found in cooked food.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241215332D          

 14 16  0  0  0  0            999 V2000
   -0.7009   -0.3708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009   -1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3609   -1.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1034   -1.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1034   -0.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3609    0.0416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958    0.8659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7834    0.1241    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3708    0.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233    1.6084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9484    1.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2784    0.7834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1034    0.7009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  0  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  2  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029748

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC2=C(C=C1)N=C1C=CC=CN21

> <INCHI_IDENTIFIER>
InChI=1S/C10H8N4/c11-8-5-4-7-10(13-8)14-6-2-1-3-9(14)12-7/h1-6H,(H2,11,13)

> <INCHI_KEY>
BUXVIXBGMQXWGT-UHFFFAOYSA-N

> <FORMULA>
C10H8N4

> <MOLECULAR_WEIGHT>
184.1973

> <EXACT_MASS>
184.074896276

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
19.236790111769295

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,8-triazatricyclo[7.4.0.0²,⁷]trideca-2(7),3,5,8,10,12-hexaen-4-amine

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
1.079598834333333

> <ALOGPS_LOGS>
-2.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.5032466122636206

> <JCHEM_POLAR_SURFACE_AREA>
56.21

> <JCHEM_REFRACTIVITY>
54.7017

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.36e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,8-triazatricyclo[7.4.0.0²,⁷]trideca-2(7),3,5,8,10,12-hexaen-4-amine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0      -1.308  -0.692   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.308  -2.232   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.540  -3.002   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.926  -2.232   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.926  -0.692   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.540   0.078   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -2.232   1.616   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       1.462   0.232   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.078   0.384   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.692   1.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.230   3.002   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.770   2.848   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.386   1.462   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.926   1.308   0.000  0.00  0.00           N+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6   10                                                       
CONECT    8    9   13                                                       
CONECT    9    1    8   10                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13    8   12   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Amino-dipyrido(1,2-a:3',2'-D)-imidazole	HMDB
2-Amino-dipyrido(1,2-a:3',2'-D)imidazole	HMDB
2-Aminodipyrido(1,2-a:3',2'-D)imidazole	HMDB
2-Aminodipyridol(1,2-a:3',2'-D)imidazole	HMDB
Dipyrido(1,2-a:3',2'-D)imidazol-2-amine	HMDB
Dipyrido[1,2-a:3',2'-D]imidazol-2-amine	HMDB
Dipyrido[1,2-a:3',2'-D]imidazol-2-amine, 9ci	HMDB
Glu-p-2	HMDB
Imidazo[1,2-a:5,4-b']dipyridin-2-amine	HMDB
Pyrido[3',2':4,5]imidazo[1,2-a]pyridin-2-amine	HMDB
Glu-p-2, monohydrobromide	HMDB
2-Aminodipyrido(1,2-a-3',2'-D)imidazole	HMDB
Glu p-2	HMDB
2-Aminodipyridoimidazole	HMDB
2-Aminodipyrido[1,2-a:3',2'-D]imidazole	KEGG

Chemical Formula

C₁₀H₈N₄

Average Molecular Weight

184.1973

Monoisotopic Molecular Weight

184.074896276

IUPAC Name

1,3,8-triazatricyclo[7.4.0.0²,⁷]trideca-2(7),3,5,8,10,12-hexaen-4-amine

Traditional Name

1,3,8-triazatricyclo[7.4.0.0²,⁷]trideca-2(7),3,5,8,10,12-hexaen-4-amine

CAS Registry Number

67730-10-3

SMILES

NC1=NC2=C(C=C1)N=C1C=CC=CN21

InChI Identifier

InChI=1S/C10H8N4/c11-8-5-4-7-10(13-8)14-6-2-1-3-9(14)12-7/h1-6H,(H2,11,13)

InChI Key

BUXVIXBGMQXWGT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as imidazopyridines. These are organic polycyclic compounds containing an imidazole ring fused to a pyridine ring. Imidazole is 5-membered ring consisting of three carbon atoms, and two nitrogen centers at the 1- and 3-positions. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyridines

Sub Class

Not Available

Direct Parent

Imidazopyridines

Alternative Parents

Substituents

Imidazopyridine
Imidazo[1,2-a]pyridine
Aminopyridine
N-substituted imidazole
Pyridine
Imidolactam
Azole
Imidazole
Heteroaromatic compound
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Amine
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

imidazopyridine (CHEBI:82331 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029748)
Cytoplasm (HMDB: HMDB0029748)

Source

Endogenous

Endogenous (HMDB: HMDB0029748)

Exogenous

Food

Food (HMDB: HMDB0029748)

Environmental

Tobacco Smoke (HMDB: HMDB0029748)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	1.38	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.41 g/L	ALOGPS
logP	1.53	ALOGPS
logP	1.08	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Basic)	3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	56.21 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	54.7 m³·mol⁻¹	ChemAxon
Polarizability	19.24 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.663	31661259
DarkChem	[M-H]-	140.849	31661259
DeepCCS	[M-2H]-	172.433	30932474
DeepCCS	[M+Na]+	147.028	30932474
AllCCS	[M+H]+	140.0	32859911
AllCCS	[M+H-H2O]+	135.6	32859911
AllCCS	[M+NH4]+	144.2	32859911
AllCCS	[M+Na]+	145.4	32859911
AllCCS	[M-H]-	141.1	32859911
AllCCS	[M+Na-2H]-	140.9	32859911
AllCCS	[M+HCOO]-	140.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Aminodipyrido[1,2-a:3',2'-d]imidazole	NC1=NC2=C(C=C1)N=C1C=CC=CN21	2635.5	Standard polar	33892256
2-Aminodipyrido[1,2-a:3',2'-d]imidazole	NC1=NC2=C(C=C1)N=C1C=CC=CN21	2115.0	Standard non polar	33892256
2-Aminodipyrido[1,2-a:3',2'-d]imidazole	NC1=NC2=C(C=C1)N=C1C=CC=CN21	2152.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Aminodipyrido[1,2-a:3',2'-d]imidazole,1TMS,isomer #1	C[Si](C)(C)NC1=CC=C2N=C3C=CC=CN3C2=N1	2300.4	Semi standard non polar	33892256
2-Aminodipyrido[1,2-a:3',2'-d]imidazole,1TMS,isomer #1	C[Si](C)(C)NC1=CC=C2N=C3C=CC=CN3C2=N1	2151.5	Standard non polar	33892256
2-Aminodipyrido[1,2-a:3',2'-d]imidazole,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=C2N=C3C=CC=CN3C2=N1)[Si](C)(C)C	2251.1	Semi standard non polar	33892256
2-Aminodipyrido[1,2-a:3',2'-d]imidazole,2TMS,isomer #1	C[Si](C)(C)N(C1=CC=C2N=C3C=CC=CN3C2=N1)[Si](C)(C)C	2235.3	Standard non polar	33892256
2-Aminodipyrido[1,2-a:3',2'-d]imidazole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C2N=C3C=CC=CN3C2=N1	2518.1	Semi standard non polar	33892256
2-Aminodipyrido[1,2-a:3',2'-d]imidazole,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C2N=C3C=CC=CN3C2=N1	2308.2	Standard non polar	33892256
2-Aminodipyrido[1,2-a:3',2'-d]imidazole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C2N=C3C=CC=CN3C2=N1)[Si](C)(C)C(C)(C)C	2700.9	Semi standard non polar	33892256
2-Aminodipyrido[1,2-a:3',2'-d]imidazole,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C1=CC=C2N=C3C=CC=CN3C2=N1)[Si](C)(C)C(C)(C)C	2640.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Aminodipyrido[1,2-a:3',2'-d]imidazole EI-B (Non-derivatized)	splash10-0059-9600000000-bb30f5b16a7ca9fbca00	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Aminodipyrido[1,2-a:3',2'-d]imidazole EI-B (Non-derivatized)	splash10-0059-9600000000-bb30f5b16a7ca9fbca00	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Aminodipyrido[1,2-a:3',2'-d]imidazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-1900000000-b18251b60a89b93e82d7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Aminodipyrido[1,2-a:3',2'-d]imidazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminodipyrido[1,2-a:3',2'-d]imidazole 10V, Positive-QTOF	splash10-000i-0900000000-c4907fc928a46bff4a62	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminodipyrido[1,2-a:3',2'-d]imidazole 20V, Positive-QTOF	splash10-000i-0900000000-d0d25839c992c1f50175	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminodipyrido[1,2-a:3',2'-d]imidazole 40V, Positive-QTOF	splash10-0pvu-2900000000-ea9da0e23c68fca8e73a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminodipyrido[1,2-a:3',2'-d]imidazole 10V, Negative-QTOF	splash10-001i-0900000000-f823fb7f0b9063aba78a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminodipyrido[1,2-a:3',2'-d]imidazole 20V, Negative-QTOF	splash10-001i-0900000000-0406f803a83d865c01f7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminodipyrido[1,2-a:3',2'-d]imidazole 40V, Negative-QTOF	splash10-0a59-1900000000-716759de6d60d04be019	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminodipyrido[1,2-a:3',2'-d]imidazole 10V, Positive-QTOF	splash10-000i-0900000000-d7abbaaf04c9d58dc21b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminodipyrido[1,2-a:3',2'-d]imidazole 20V, Positive-QTOF	splash10-000i-0900000000-d7abbaaf04c9d58dc21b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminodipyrido[1,2-a:3',2'-d]imidazole 40V, Positive-QTOF	splash10-000i-0900000000-d17c24f8579337bd2d9f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminodipyrido[1,2-a:3',2'-d]imidazole 10V, Negative-QTOF	splash10-001i-0900000000-805e62e5c1dff1cef8f1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminodipyrido[1,2-a:3',2'-d]imidazole 20V, Negative-QTOF	splash10-001i-0900000000-805e62e5c1dff1cef8f1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Aminodipyrido[1,2-a:3',2'-d]imidazole 40V, Negative-QTOF	splash10-001i-0900000000-38e47564b12818115297	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000949

KNApSAcK ID

Not Available

Chemspider ID

45326

KEGG Compound ID

C19245

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

49970

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-Aminodipyrido[1,2-a:3',2'-d]imidazole (HMDB0029748)

MOL for HMDB0029748 (2-Aminodipyrido[1,2-a:3',2'-d]imidazole)

3D MOL for HMDB0029748 (2-Aminodipyrido[1,2-a:3',2'-d]imidazole)

3D SDF for HMDB0029748 (2-Aminodipyrido[1,2-a:3',2'-d]imidazole)

3D-SDF for HMDB0029748 (2-Aminodipyrido[1,2-a:3',2'-d]imidazole)

PDB for HMDB0029748 (2-Aminodipyrido[1,2-a:3',2'-d]imidazole)

3D PDB for HMDB0029748 (2-Aminodipyrido[1,2-a:3',2'-d]imidazole)

SMILES for HMDB0029748 (2-Aminodipyrido[1,2-a:3',2'-d]imidazole)

INCHI for HMDB0029748 (2-Aminodipyrido[1,2-a:3',2'-d]imidazole)

Structure for HMDB0029748 (2-Aminodipyrido[1,2-a:3',2'-d]imidazole)

3D Structure for HMDB0029748 (2-Aminodipyrido[1,2-a:3',2'-d]imidazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra