NP-MRD: Showing NP-Card for n-(7-chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl})carbamoyl]oxy}-hexahydro-1h-pyrrolizin-1-yl)ethanimidic acid (NP0281484)

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Record Information

Version

2.0

Created at

2022-09-09 07:51:25 UTC

Updated at

2022-09-09 07:51:25 UTC

NP-MRD ID

NP0281484

Secondary Accession Numbers

None

Natural Product Identification

Common Name

n-(7-chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl})carbamoyl]oxy}-hexahydro-1h-pyrrolizin-1-yl)ethanimidic acid

Description

N-(7-chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]Nonan-8-yl})carbamoyl]oxy}-hexahydro-1H-pyrrolizin-1-yl)ethanimidic acid 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-(7-chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl})carbamoyl]oxy}-hexahydro-1h-pyrrolizin-1-yl)ethanimidic acid is found in Lolium temulentum. N-(7-chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]Nonan-8-yl})carbamoyl]oxy}-hexahydro-1H-pyrrolizin-1-yl)ethanimidic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171520322D          

 27 31  0  0  0  0            999 V2000
   -0.3273    0.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4266    0.6108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0937    0.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2894   -0.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3035    0.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1808    0.8323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0598    0.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3351    0.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6160   -0.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9655   -0.9921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0865    0.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5134    1.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2673    1.7663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1537    1.9166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0670    2.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6797    3.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3436    4.0429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5146    4.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2001    5.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8129    4.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6199    4.8806    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4768    3.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478    3.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4012    2.8130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0690    3.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9833    4.1180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8225    2.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  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  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
  3 11  1  0  0  0  0
  6 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
   -2.8458    4.3522    1.7767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825    3.9715    0.4273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7685    4.9146   -0.1917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3573    2.6436   -0.0343 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4113    1.3934   -0.5009 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7380    0.3477    0.4246 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6822   -0.3280   -0.2181 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6009   -0.3351    0.2571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7937    0.3199    1.3361 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -1.0323   -0.4064 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3299   -1.7023   -1.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9450   -0.9918    0.2187 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0515   -0.3096   -0.5783 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3167   -1.3366   -1.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0868   -2.6263   -0.9962 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4019   -3.2450   -0.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0297   -2.6720    0.3887 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9901   -1.7243    0.9001 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1039   -0.4531    0.3501 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6756   -2.2996    0.3430 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7877   -0.6464    0.7550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0197   -0.2398    0.1954 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0129    0.2140    1.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8049    1.3136    0.4255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9219    1.7387   -0.7375 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.9426    1.6274   -2.2140 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7859    0.7849   -0.7714 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9431    4.2839    1.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4043    5.2855    2.1577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4827    3.5809    2.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6704    3.0640   -1.1221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8827    1.1738   -1.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904    0.8363    1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3080   -1.0059   -2.4790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8734   -2.6486   -1.8169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2506   -2.0431   -1.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9206   -0.4173    1.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8535    0.6880   -0.8795 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3764   -1.2640   -2.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6804   -1.2657   -2.5201 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0140   -2.9381   -1.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3622   -4.3293   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9804   -2.1454    0.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2332   -3.4827    1.1450 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9594   -1.6942    2.0103 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2358   -3.0470    0.9484 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8967   -0.6411    1.8798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130   -1.6997    0.5171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6350    0.5070    2.1097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7308   -0.6245    1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9268    2.1200    1.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8091    0.9670    0.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6808    2.7931   -0.6207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8258    0.2677   -1.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  6  1  0
  6 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 20 12  1  0
  5  6  1  0
 19 13  1  0
 27 22  1  0
 20 15  1  0
 11 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  1
 13 38  1  6
 14 39  1  0
 14 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  1
 20 46  1  1
  6 33  1  1
 21 47  1  0
 21 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 25 53  1  1
 27 54  1  6
  5 32  1  6
  4 31  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END


  Mrv1533004171520322D          

 27 31  0  0  0  0            999 V2000
   -0.3273    0.2758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4266    0.6108    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0937    0.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2894   -0.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3035    0.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1808    0.8323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0598    0.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3351    0.0128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6160   -0.4733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9655   -0.9921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0865    0.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5134    1.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2673    1.7663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1537    1.9166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0670    2.7371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6797    3.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3436    4.0429    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5146    4.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2001    5.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8129    4.7096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6199    4.8806    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4768    3.9562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6478    3.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4012    2.8130    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0690    3.2975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9833    4.1180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8225    2.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  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  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
  3 11  1  0  0  0  0
  6 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0281484

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C1C2CN3CCC(O2)C13)C(=O)OC1CN2CCC(Cl)C2C1NC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H27ClN4O4/c1-9(24)20-14-12(7-22-5-3-10(19)15(14)22)27-18(25)21(2)16-13-8-23-6-4-11(26-13)17(16)23/h10-17H,3-8H2,1-2H3,(H,20,24)

> <INCHI_KEY>
CPFZPQRTCRBNRM-UHFFFAOYSA-N

> <FORMULA>
C18H27ClN4O4

> <MOLECULAR_WEIGHT>
398.89

> <EXACT_MASS>
398.1720831

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.22389417182185

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7-chloro-1-acetamido-hexahydro-1H-pyrrolizin-2-yl N-methyl-N-{2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl}carbamate

> <ALOGPS_LOGP>
-0.12

> <JCHEM_LOGP>
-0.5465475646666658

> <ALOGPS_LOGS>
-1.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.635460740433466

> <JCHEM_PKA_STRONGEST_BASIC>
7.086272995813805

> <JCHEM_POLAR_SURFACE_AREA>
74.35000000000001

> <JCHEM_REFRACTIVITY>
96.94889999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.14e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-chloro-1-acetamido-hexahydro-1H-pyrrolizin-2-yl N-methyl-N-{2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl}carbamate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -0.611   0.515   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       0.796   1.140   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.042   0.234   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.407  -0.811   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.433   1.227   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       4.071   1.554   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.712   1.510   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.226   0.024   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.883  -0.884   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.669  -1.852   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.895   0.191   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.958   2.672   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.366   3.297   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.287   3.578   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.125   5.109   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.269   6.140   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -0.641   7.547   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -0.961   9.053   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.374   9.823   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.517   8.791   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0       3.024   9.110   0.000  0.00  0.00          Cl+0
HETATM   22  C   UNK     0       0.890   7.385   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.209   5.878   0.000  0.00  0.00           C+0
HETATM   24  N   UNK     0       2.616   5.251   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       3.862   6.155   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       3.702   7.687   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.269   5.528   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9    3    6                                                  
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   17   23                                                  
CONECT   23   22   15   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Value	Source
N-(7-Chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0,]nonan-8-yl})carbamoyl]oxy}-hexahydro-1H-pyrrolizin-1-yl)ethanimidate	Generator
N-(7-Chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl})carbamoyl]oxy}-hexahydro-1H-pyrrolizin-1-yl)ethanimidate	Generator

Chemical Formula

C₁₈H₂₇ClN₄O₄

Average Mass

398.8900 Da

Monoisotopic Mass

398.17208 Da

IUPAC Name

7-chloro-1-acetamido-hexahydro-1H-pyrrolizin-2-yl N-methyl-N-{2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl}carbamate

Traditional Name

7-chloro-1-acetamido-hexahydro-1H-pyrrolizin-2-yl N-methyl-N-{2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl}carbamate

CAS Registry Number

Not Available

SMILES

CN(C1C2CN3CCC(O2)C13)C(=O)OC1CN2CCC(Cl)C2C1NC(C)=O

InChI Identifier

InChI=1S/C18H27ClN4O4/c1-9(24)20-14-12(7-22-5-3-10(19)15(14)22)27-18(25)21(2)16-13-8-23-6-4-11(26-13)17(16)23/h10-17H,3-8H2,1-2H3,(H,20,24)

InChI Key

CPFZPQRTCRBNRM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Lolium temulentum	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Loline alkaloids and derivatives

Sub Class

Not Available

Direct Parent

Loline alkaloids and derivatives

Alternative Parents

Substituents

Loline
Pyrrolizidine
Para-oxazepine
Morpholine
Oxazinane
N-alkylpyrrolidine
Pyrrolidine
Tetrahydrofuran
Carbamic acid ester
Carbonic acid derivative
Tertiary amine
Tertiary aliphatic amine
Carboximidic acid
Carboximidic acid derivative
Dialkyl ether
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Alkyl halide
Organochloride
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Amine
Carbonyl group
Organic nitrogen compound
Alkyl chloride
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	-0.12	ALOGPS
logP	-0.55	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	13.64	ChemAxon
pKa (Strongest Basic)	7.09	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.35 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	96.95 m³·mol⁻¹	ChemAxon
Polarizability	40.22 Å³	ChemAxon
Number of Rings	5	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

75953658

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for n-(7-chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl})carbamoyl]oxy}-hexahydro-1h-pyrrolizin-1-yl)ethanimidic acid (NP0281484)

MOL for NP0281484 (n-(7-chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl})carbamoyl]oxy}-hexahydro-1h-pyrrolizin-1-yl)ethanimidic acid)

3D MOL for NP0281484 (n-(7-chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl})carbamoyl]oxy}-hexahydro-1h-pyrrolizin-1-yl)ethanimidic acid)

3D SDF for NP0281484 (n-(7-chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl})carbamoyl]oxy}-hexahydro-1h-pyrrolizin-1-yl)ethanimidic acid)

3D-SDF for NP0281484 (n-(7-chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl})carbamoyl]oxy}-hexahydro-1h-pyrrolizin-1-yl)ethanimidic acid)

PDB for NP0281484 (n-(7-chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl})carbamoyl]oxy}-hexahydro-1h-pyrrolizin-1-yl)ethanimidic acid)

3D PDB for NP0281484 (n-(7-chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl})carbamoyl]oxy}-hexahydro-1h-pyrrolizin-1-yl)ethanimidic acid)

SMILES for NP0281484 (n-(7-chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl})carbamoyl]oxy}-hexahydro-1h-pyrrolizin-1-yl)ethanimidic acid)

INCHI for NP0281484 (n-(7-chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl})carbamoyl]oxy}-hexahydro-1h-pyrrolizin-1-yl)ethanimidic acid)

Structure for NP0281484 (n-(7-chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl})carbamoyl]oxy}-hexahydro-1h-pyrrolizin-1-yl)ethanimidic acid)

3D Structure for NP0281484 (n-(7-chloro-2-{[methyl({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-yl})carbamoyl]oxy}-hexahydro-1h-pyrrolizin-1-yl)ethanimidic acid)