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Showing NP-Card for N-Norgramine (NP0336070)

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Record Information
Version2.0
Created at2024-09-11 04:36:07 UTC
Updated at2024-09-11 04:36:07 UTC
NP-MRD IDNP0336070
Secondary Accession NumbersNone
Natural Product Identification
Common NameN-Norgramine
DescriptionN-Norgramine, also known as NMAMI, belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. An aminoalkylindole that is indole carrying a methylaminomethyl substituent at postion 3. N-Norgramine is a very strong basic compound (based on its pKa). Outside of the human body, N-Norgramine has been detected, but not quantified in, barley and cereals and cereal products. N-Norgramine was first documented in 1982 (PMID: 7141562). This could make N-norgramine a potential biomarker for the consumption of these foods (PMID: 16662926) (PMID: 16664431) (PMID: 16930646).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336070 (N-Norgramine)


  Mrv0541 05061310282D          

 12 13  0  0  0  0            999 V2000
   -0.1781   -0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   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
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   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
    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 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
    0.0768   -0.1006    0.0000 N   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
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  8  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  4  2  0  0  0  0
  9  8  1  0  0  0  0
 10  5  2  0  0  0  0
 10  9  1  0  0  0  0
 11  1  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
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3D MOL for NP0336070 (N-Norgramine)

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3D SDF for NP0336070 (N-Norgramine)

  Mrv0541 05061310282D          

 12 13  0  0  0  0            999 V2000
   -0.1781   -0.8853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   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
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   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
    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 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
    0.0768   -0.1006    0.0000 N   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
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  8  6  1  0  0  0  0
  8  7  2  0  0  0  0
  9  4  2  0  0  0  0
  9  8  1  0  0  0  0
 10  5  2  0  0  0  0
 10  9  1  0  0  0  0
 11  1  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336070

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNCC1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2/c1-11-6-8-7-12-10-5-3-2-4-9(8)10/h2-5,7,11-12H,6H2,1H3

> <INCHI_KEY>
BIFJNBXQXNWYOL-UHFFFAOYSA-N

> <FORMULA>
C10H12N2

> <MOLECULAR_WEIGHT>
160.2157

> <EXACT_MASS>
160.100048394

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
18.43543237196538

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1H-indol-3-ylmethyl)(methyl)amine

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
1.6303566386666666

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.976088744410646

> <JCHEM_PKA_STRONGEST_BASIC>
9.864928489298677

> <JCHEM_POLAR_SURFACE_AREA>
27.82

> <JCHEM_REFRACTIVITY>
50.39249999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1H-indol-3-ylmethyl)(methyl)amine

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0336070 (N-Norgramine)
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PDB for NP0336070 (N-Norgramine)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -0.332  -1.653   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.143  -0.188   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
CONECT    1   11                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    9                                                       
CONECT    5    3   10                                                       
CONECT    6    8   11                                                       
CONECT    7    8   12                                                       
CONECT    8    6    7    9                                                  
CONECT    9    4    8   10                                                  
CONECT   10    5    9   12                                                  
CONECT   11    1    6                                                       
CONECT   12    7   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0336070 (N-Norgramine)
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SMILES for NP0336070 (N-Norgramine)
CNCC1=CNC2=CC=CC=C12
Download
INCHI for NP0336070 (N-Norgramine)
InChI=1S/C10H12N2/c1-11-6-8-7-12-10-5-3-2-4-9(8)10/h2-5,7,11-12H,6H2,1H3
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Synonyms
ValueSource
(1H-indol-3-yl)-N-MethylmethanamineChEBI
(indol-3-yl)-N-MethylmethanamineChEBI
N-Methyl-3-aminomethylindoleChEBI
N-Methyl-N-(indol-3-ylmethyl)amineChEBI
NMAMIChEBI
3-(Methylaminomethyl)indoleHMDB
N-NorgramineChEBI
Chemical FormulaC10H12N2
Average Mass160.2157 Da
Monoisotopic Mass160.10005 Da
IUPAC Name(1H-indol-3-ylmethyl)(methyl)amine
Traditional Name(1H-indol-3-ylmethyl)(methyl)amine
CAS Registry NumberNot Available
SMILES
CNCC1=CNC2=CC=CC=C12
InChI Identifier
InChI=1S/C10H12N2/c1-11-6-8-7-12-10-5-3-2-4-9(8)10/h2-5,7,11-12H,6H2,1H3
InChI KeyBIFJNBXQXNWYOL-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndoles  
Direct Parent3-alkylindoles  
Alternative Parents
Substituents
  • 3-alkylindole
    • 

  • Aralkylamine
    • 

  • Benzenoid
    • 

  • Substituted pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Pyrrole
    • 

  • Azacycle
    • 

  • Secondary amine
    • 

  • Secondary aliphatic amine
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.55ALOGPS
logP1.63ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)15.98ChemAxon
pKa (Strongest Basic)9.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area27.82 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.39 m³·mol⁻¹ChemAxon
Polarizability18.44 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0038456  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB017815  
KNApSAcK IDNot Available
Chemspider ID87011  
KEGG Compound IDNot Available
BioCyc IDCPD-8914  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound96388  
PDB IDNot Available
ChEBI ID137310  
Good Scents IDNot Available
References
General References
  1. Hanson AD, Ditz KM, Singletary GW, Leland TJ: Gramine Accumulation in Leaves of Barley Grown under High-Temperature Stress. Plant Physiol. 1983 Apr;71(4):896-904. doi: 10.1104/pp.71.4.896. [PubMed:16662926  ] 
  2. Leland TJ, Hanson AD: Induction of a Specific N-Methyltransferase Enzyme by Long-Term Heat Stress during Barley Leaf Growth. Plant Physiol. 1985 Oct;79(2):451-7. doi: 10.1104/pp.79.2.451. [PubMed:16664431  ] 
  3. Larsson KA, Zetterlund I, Delp G, Jonsson LM: N-Methyltransferase involved in gramine biosynthesis in barley: cloning and characterization. Phytochemistry. 2006 Sep;67(18):2002-8. doi: 10.1016/j.phytochem.2006.06.036.  Epub 2006 Aug 22. [PubMed:16930646  ] 
  4. Mangino MM, Libbey LM, Scanlan RA: Nitrosation of N-methyltyramine and N-methyl-3-aminomethylindole, two barley malt alkaloids. IARC Sci Publ. 1982;(41):57-69. [PubMed:7141562  ]