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Showing NP-Card for Norloline (NP0066259)

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Record Information
Version2.0
Created at2022-04-28 10:29:43 UTC
Updated at2022-04-28 10:29:43 UTC
NP-MRD IDNP0066259
Secondary Accession NumbersNone
Natural Product Identification
Common NameNorloline
Description(1R,3S,7S,8S)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]Nonan-8-amine 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. Norloline is found in Lolium cuneatum. Based on a literature review very few articles have been published on (1R,3S,7S,8S)-2-oxa-6-azatricyclo[4.2.1.0³,⁷]Nonan-8-amine.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0066259 (Norloline)


  Mrv1652304282212302D          

 10 12  0  0  1  0            999 V2000
    1.0743   -1.8602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4096   -1.3351    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9256   -0.7530    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8416   -0.0226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6977   -0.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358   -1.2797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9081   -0.7115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5602   -0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0462   -0.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3027   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  6  0  0  0
  6  7  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  6  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
M  END
Download

3D MOL for NP0066259 (Norloline)

     RDKit          3D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -2.4731   -0.4849    0.7983 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3949    0.4228    0.6796 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0277   -0.2238    0.9143 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0543   -1.0923   -0.3181 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5320   -1.0746   -0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0268    0.1564    0.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8484    0.8624    0.5780 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1930    1.5651   -0.5294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0749    0.7763   -0.7829 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7028   -0.4560   -1.2951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4995   -0.8805    1.7396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5610   -1.1721    0.0219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5452    1.3202    1.2782 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0988   -0.6956    1.8513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3316   -2.1117   -0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9608   -1.9966   -0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7718   -1.1126   -1.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6433   -0.1175    0.9648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6428    0.8083   -0.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8347    1.6555   -1.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1390    2.5633   -0.1296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8570    1.2877   -1.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4 10  1  0
  4  3  1  0
  3  2  1  0
 10  9  1  0
  3  7  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  1
  9 22  1  6
  8 20  1  0
  8 21  1  0
  6 18  1  0
  6 19  1  0
  5 16  1  0
  5 17  1  0
  4 15  1  1
  3 14  1  1
M  END
Download

3D SDF for NP0066259 (Norloline)


  Mrv1652304282212302D          

 10 12  0  0  1  0            999 V2000
    1.0743   -1.8602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4096   -1.3351    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9256   -0.7530    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8416   -0.0226    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6977   -0.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7358   -1.2797    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9081   -0.7115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5602   -0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0462   -0.0142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3027   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  1  1  6  0  0  0
  6  7  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  1  6  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0066259

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C7H12N2O/c8-6-5-3-9-2-1-4(10-5)7(6)9/h4-7H,1-3,8H2/t4-,5+,6+,7+/m0/s1

> <INCHI_KEY>
SOFXQTNEGHNRMN-BDVNFPICSA-N

> <FORMULA>
C7H12N2O

> <MOLECULAR_WEIGHT>
140.186

> <EXACT_MASS>
140.094963014

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
14.789402587285782

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.00

> <JCHEM_LOGP>
-0.8693366623333336

> <ALOGPS_LOGS>
0.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
8.912983295520558

> <JCHEM_POLAR_SURFACE_AREA>
38.489999999999995

> <JCHEM_REFRACTIVITY>
36.6206

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e+03 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0066259 (Norloline)

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PDB for NP0066259 (Norloline)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  O   UNK     0       2.005  -3.472   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.765  -2.492   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.728  -1.406   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.571  -0.042   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.169  -0.338   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.240  -2.389   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.562  -1.328   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       4.779  -0.385   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.086  -0.027   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.565  -1.536   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    3    8                                                  
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9    2                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   24    0
END

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3D PDB for NP0066259 (Norloline)
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SMILES for NP0066259 (Norloline)
N[C@@H]1[C@H]2CN3CC[C@H](O2)[C@H]13
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INCHI for NP0066259 (Norloline)
InChI=1S/C7H12N2O/c8-6-5-3-9-2-1-4(10-5)7(6)9/h4-7H,1-3,8H2/t4-,5+,6+,7+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC7H12N2O
Average Mass140.1860 Da
Monoisotopic Mass140.09496 Da
IUPAC Name(1R,3S,7S)-2-oxa-6-azatricyclo[4.2.1.0^{3,7}]nonan-8-amine
Traditional Name(1R,3S,7S)-2-oxa-6-azatricyclo[4.2.1.0^{3,7}]nonan-8-amine
CAS Registry NumberNot Available
SMILES
N[C@@H]1[C@H]2CN3CC[C@H](O2)[C@H]13
InChI Identifier
InChI=1S/C7H12N2O/c8-6-5-3-9-2-1-4(10-5)7(6)9/h4-7H,1-3,8H2/t4-,5+,6+,7+/m0/s1
InChI KeySOFXQTNEGHNRMN-BDVNFPICSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Lolium cuneatumPlant
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
    • 

  • N-alkylpyrrolidine
    • 

  • Oxazinane
    • 

  • Morpholine
    • 

  • Tetrahydrofuran
    • 

  • Pyrrolidine
    • 

  • Tertiary aliphatic amine
    • 

  • Tertiary amine
    • 

  • Oxacycle
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary amine
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Primary aliphatic amine
    • 

  • Amine
    • 

  • 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-1ALOGPS
logP-0.87ChemAxon
logS0.86ALOGPS
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.49 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity36.62 m³·mol⁻¹ChemAxon
Polarizability14.79 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID113608390  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound906359  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References