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Showing NP-Card for n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]carboximidic acid (NP0326689)

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Record Information
Version2.0
Created at2022-09-12 08:30:36 UTC
Updated at2022-09-12 08:30:36 UTC
NP-MRD IDNP0326689
Secondary Accession NumbersNone
Natural Product Identification
Common Namen-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]carboximidic acid
DescriptionN-Formylnorloline belongs to the class of organic compounds known as loline alkaloids and derivatives. These are alkaloids with a structure characterized by a saturated pyrrolizidine ring, a primary amine at the C-1 carbon, and an internal ether bridge joining two distant ring (C-2 and C-7) carbons. Different substituents at the C-1 amine, such as methyl, formyl, and acetyl groups, yield various loline species. n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]carboximidic acid is found in Epichloe coenophiala and Lolium temulentum. n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]carboximidic acid was first documented in 1991 (PMID: 1893500). Based on a literature review very few articles have been published on N-Formylnorloline.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0326689 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]carboximidic acid)


  Mrv1652309122210302D          

 12 14  0  0  1  0            999 V2000
   -1.8496   -0.1041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1824   -0.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4286   -0.2544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386   -0.7398    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2313   -0.7631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3256   -0.0329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2047   -0.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800   -0.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7608   -1.3386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1104   -1.8574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4343   -1.2995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4483   -0.2078    0.0000 O   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
  4  3  1  6  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  1  0  0  0  0
  5  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  1  0  0  0
  6 12  1  1  0  0  0
M  END
Download

3D MOL for NP0326689 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]carboximidic acid)

     RDKit          3D

 24 26  0  0  0  0  0  0  0  0999 V2000
    3.5932    0.5722    0.4711 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9278   -0.4528    1.1020 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8038   -0.9393    0.7332 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1308   -0.4225   -0.4187 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1816    0.7099    0.0034 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7303    0.7214   -1.1955 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0992    0.8845   -0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8513    0.8326    0.9386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6118    0.0425    0.9921 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8601   -1.2904    0.4121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0228   -1.3495   -0.8441 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6477   -0.5433   -1.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6374    0.6628   -0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3816   -0.9042    1.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667   -0.1442   -1.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6564    1.6174    0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5067    1.5377   -1.9040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8208    0.1261   -0.8878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4996    1.8975   -0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5695    1.8461    1.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6538    0.3731    1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9392   -1.3754    0.1840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5535   -2.0895    1.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2870   -2.3127   -1.1686 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4 11  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6 12  1  0
  6  5  1  0
  5  4  1  0
 12 11  1  0
  5  9  1  0
  1 13  1  0
  2 14  1  0
  4 15  1  6
 11 24  1  6
 10 22  1  0
 10 23  1  0
  8 20  1  0
  8 21  1  0
  7 18  1  0
  7 19  1  0
  6 17  1  6
  5 16  1  1
M  END
Download

3D SDF for NP0326689 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]carboximidic acid)


  Mrv1652309122210302D          

 12 14  0  0  1  0            999 V2000
   -1.8496   -0.1041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1824   -0.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4286   -0.2544    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2386   -0.7398    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2313   -0.7631    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3256   -0.0329    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2047   -0.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800   -0.8525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7608   -1.3386    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1104   -1.8574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4343   -1.2995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4483   -0.2078    0.0000 O   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
  4  3  1  6  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  1  0  0  0  0
  5  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
 11 12  1  1  0  0  0
  6 12  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0326689

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC=N[C@H]1[C@H]2CN3CC[C@H](O2)[C@H]13

> <INCHI_IDENTIFIER>
InChI=1S/C8H12N2O2/c11-4-9-7-6-3-10-2-1-5(12-6)8(7)10/h4-8H,1-3H2,(H,9,11)/t5-,6+,7-,8+/m0/s1

> <INCHI_KEY>
XKEMMYSNKGUOCT-FKSUSPILSA-N

> <FORMULA>
C8H12N2O2

> <MOLECULAR_WEIGHT>
168.196

> <EXACT_MASS>
168.089877634

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
16.90410043710846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(1R,3S,7S,8R)-2-oxa-6-azatricyclo[4.2.1.0^{3,7}]nonan-8-yl]carboximidic acid

> <JCHEM_LOGP>
-2.9146654893633803

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.36085211999753

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.75873442929225

> <JCHEM_PKA_STRONGEST_BASIC>
7.701297033747358

> <JCHEM_POLAR_SURFACE_AREA>
45.06

> <JCHEM_REFRACTIVITY>
42.09560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1R,3S,7S,8R)-2-oxa-6-azatricyclo[4.2.1.0^{3,7}]nonan-8-yl]carboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0326689 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]carboximidic acid)

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PDB for NP0326689 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]carboximidic acid)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0      -3.453  -0.194   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -2.207  -1.100   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      -0.800  -0.475   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.445  -1.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.298  -1.424   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.475  -0.061   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.115  -0.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.629  -1.591   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.287  -2.499   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.073  -3.467   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.811  -2.426   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.837  -0.388   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10    4   12                                                  
CONECT   12   11    6                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   28    0
END

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3D PDB for NP0326689 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]carboximidic acid)
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SMILES for NP0326689 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]carboximidic acid)
OC=N[C@H]1[C@H]2CN3CC[C@H](O2)[C@H]13
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INCHI for NP0326689 (n-[(1r,3s,7s,8r)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl]carboximidic acid)
InChI=1S/C8H12N2O2/c11-4-9-7-6-3-10-2-1-5(12-6)8(7)10/h4-8H,1-3H2,(H,9,11)/t5-,6+,7-,8+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC8H12N2O2
Average Mass168.1960 Da
Monoisotopic Mass168.08988 Da
IUPAC NameN-[(1R,3S,7S,8R)-2-oxa-6-azatricyclo[4.2.1.0^{3,7}]nonan-8-yl]carboximidic acid
Traditional NameN-[(1R,3S,7S,8R)-2-oxa-6-azatricyclo[4.2.1.0^{3,7}]nonan-8-yl]carboximidic acid
CAS Registry NumberNot Available
SMILES
OC=N[C@H]1[C@H]2CN3CC[C@H](O2)[C@H]13
InChI Identifier
InChI=1S/C8H12N2O2/c11-4-9-7-6-3-10-2-1-5(12-6)8(7)10/h4-8H,1-3H2,(H,9,11)/t5-,6+,7-,8+/m0/s1
InChI KeyXKEMMYSNKGUOCT-FKSUSPILSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acremonium coenophialumLOTUS Database
Lolium temulentumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as loline alkaloids and derivatives. These are alkaloids with a structure characterized by  a saturated pyrrolizidine ring, a primary amine at the C-1 carbon, and an internal ether bridge joining two distant ring (C-2 and C-7) carbons. Different substituents at the C-1 amine, such as methyl, formyl, and acetyl groups, yield various loline species.
KingdomOrganic compounds  
Super ClassAlkaloids and derivatives  
ClassLoline alkaloids and derivatives  
Sub ClassNot Available
Direct ParentLoline alkaloids and derivatives  
Alternative Parents
Substituents
  • Loline
    • 

  • Pyrrolizidine
    • 

  • Para-oxazepine
    • 

  • Morpholine
    • 

  • Oxazinane
    • 

  • N-alkylpyrrolidine
    • 

  • Oxolane
    • 

  • Pyrrolidine
    • 

  • Amino acid or derivatives
    • 

  • Carboxamide group
    • 

  • Tertiary aliphatic amine
    • 

  • Tertiary amine
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxylic acid derivative
    • 

  • Dialkyl ether
    • 

  • Ether
    • 

  • Oxacycle
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Amine
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic 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
logP-2.9ChemAxon
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)7.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area45.06 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity42.1 m³·mol⁻¹ChemAxon
Polarizability16.9 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00023614  
Chemspider ID68025754  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound78358525  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Takeda A, Suzuki E, Kamei K, Nakata H: Detection and identification of loline and its analogues in horse urine. Chem Pharm Bull (Tokyo). 1991 Apr;39(4):964-8. doi: 10.1248/cpb.39.964. [PubMed:1893500  ] 
  2. LOTUS database [Link]