NP-MRD: Showing NP-Card for n-{7-chloro-2-[({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-ylmethyl}-c-hydroxycarbonimidoyl)oxy]-hexahydro-1h-pyrrolizin-1-yl}ethanimidic acid (NP0270189)

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Record Information

Version

2.0

Created at

2022-09-08 15:56:45 UTC

Updated at

2022-09-08 15:56:45 UTC

NP-MRD ID

NP0270189

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Lolidine belongs to the class of organic compounds known as pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom. n-{7-chloro-2-[({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-ylmethyl}-c-hydroxycarbonimidoyl)oxy]-hexahydro-1h-pyrrolizin-1-yl}ethanimidic acid is found in Lolium temulentum. Based on a literature review very few articles have been published on Lolidine.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082217562D          

 27 31  0  0  0  0            999 V2000
   -1.1651    3.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8328    3.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863    3.3775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7471    2.2209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4149    1.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4154    0.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7483    0.4261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9944    0.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9076    1.5816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273    0.2758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4266    0.6108    0.0000 C   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
   -3.2002    0.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6847    1.3248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4692    1.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4686    2.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6838    2.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4284    3.4441    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1993    1.9919    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
  2  4  2  0  0  0  0
  4  5  1  4  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
  8 10  2  0  0  0  0
 10 11  1  4  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 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
 13 19  1  0  0  0  0
 18 20  1  0  0  0  0
 12 20  1  0  0  0  0
 15 20  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  5 27  1  0  0  0  0
 22 27  1  0  0  0  0
M  END

     RDKit          3D

 54 58  0  0  0  0  0  0  0  0999 V2000
   -4.6601    2.2497   -1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6240    2.3492    0.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3323    3.3812    0.8226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9794    1.5388    0.9686 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2374    0.4621    0.3925 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6653   -0.8888    0.9175 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.6794   -1.4782   -0.0168 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3561   -2.9637    0.6685 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.8785   -1.7933   -1.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4623   -1.8518   -0.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4965   -1.7074    0.6512 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3385   -0.8745    0.9996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7524    0.5343    0.7475 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0981    1.1587   -0.3111 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2615    1.4200   -0.3828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7739    1.7691   -1.6238 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9394    1.3202    0.6940 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3590    1.5494    0.8297 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0848    0.7619   -0.2019 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7971   -0.7412   -0.0299 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8448   -1.2798   -0.9784 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9680   -0.3403   -0.8782 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0597   -1.1029   -0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6035   -1.2361    1.1845 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4613   -0.2563    1.3547 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2192   -0.9227    1.2811 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5758    0.6006    0.1446 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6278    2.2193   -1.6972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1484    3.1254   -1.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1347    1.2925   -1.5872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0228    3.8773    1.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3935    0.4573   -0.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9409   -0.8956    1.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4536   -0.7493   -0.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1436   -2.7796   -1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0031   -0.9991   -2.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9332   -2.7887   -1.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8844   -1.0254   -1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0590   -1.0104    2.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5096   -1.2356    0.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6111    1.1402    1.6709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4188    1.3652   -2.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6738    1.1865    1.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6037    2.6221    0.7062 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9705    1.0905   -1.2325 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7909   -1.0112   -0.2457 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1377   -2.3076   -0.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4070   -1.1568   -2.0118 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1098   -2.1006   -0.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0272   -0.6143   -0.3569 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4321   -0.9173    1.8370 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2092   -2.2382    1.4232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5812    0.2882    2.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1161    1.5070    0.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  4  5  1  0
  5 13  1  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  1  0
  7  6  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 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
  6  5  1  0
 27 19  1  0
  6 11  1  0
 26 20  1  0
 27 22  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  5 32  1  6
 13 41  1  1
 12 39  1  0
 12 40  1  0
 10 37  1  0
 10 38  1  0
  9 35  1  0
  9 36  1  0
  7 34  1  6
  6 33  1  1
 16 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  6
 20 46  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  1
M  END


  Mrv1652309082217562D          

 27 31  0  0  0  0            999 V2000
   -1.1651    3.5260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8328    3.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863    3.3775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7471    2.2209    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4149    1.7365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4154    0.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7483    0.4261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9944    0.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9076    1.5816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273    0.2758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4266    0.6108    0.0000 C   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
   -3.2002    0.6570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6847    1.3248    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4692    1.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4686    2.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6838    2.6597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4284    3.4441    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.1993    1.9919    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
  2  4  2  0  0  0  0
  4  5  1  4  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
  8 10  2  0  0  0  0
 10 11  1  4  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 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
 13 19  1  0  0  0  0
 18 20  1  0  0  0  0
 12 20  1  0  0  0  0
 15 20  1  0  0  0  0
  6 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
  5 27  1  0  0  0  0
 22 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0270189

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)=NC1C(CN2CCC(Cl)C12)OC(O)=NCC1C2CN3CCC(O2)C13

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

> <INCHI_KEY>
MEQYZLVMLXTKEV-UHFFFAOYSA-N

> <FORMULA>
C18H27ClN4O4

> <MOLECULAR_WEIGHT>
398.89

> <EXACT_MASS>
398.1720831

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
40.836131530569055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(7-chloro-2-{[({2-oxa-6-azatricyclo[4.2.1.0^{3,7}]nonan-8-yl}methyl)-C-hydroxycarbonimidoyl]oxy}-hexahydro-1H-pyrrolizin-1-yl)ethanimidic acid

> <JCHEM_LOGP>
-3.9232067697032624

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
5.01118025233657

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.1528852741348734

> <JCHEM_PKA_STRONGEST_BASIC>
8.055920592636657

> <JCHEM_POLAR_SURFACE_AREA>
90.12

> <JCHEM_REFRACTIVITY>
98.25169999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
N-{7-chloro-2-[({2-oxa-6-azatricyclo[4.2.1.0^{3,7}]nonan-8-ylmethyl}-C-hydroxycarbonimidoyl)oxy]-hexahydro-1H-pyrrolizin-1-yl}ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.175   6.582   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.421   5.677   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.828   6.305   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      -3.261   4.146   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -4.508   3.241   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.509   1.701   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.264   0.795   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.856   1.421   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.694   2.952   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      -0.611   0.515   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.796   1.140   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.042   0.234   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.407  -0.811   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.433   1.227   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       4.071   1.554   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       5.712   1.510   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.226   0.024   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.883  -0.884   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.669  -1.852   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.895   0.191   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.974   1.226   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -6.878   2.473   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -8.342   2.950   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.341   4.490   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -6.876   4.965   0.000  0.00  0.00           C+0
HETATM   26 Cl   UNK     0      -6.400   6.429   0.000  0.00  0.00          Cl+0
HETATM   27  C   UNK     0      -5.972   3.718   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   27                                                  
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   13                                                       
CONECT   20   18   12   15                                                  
CONECT   21    6   22                                                       
CONECT   22   21   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    5   22                                                  
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₂₇ClN₄O₄

Average Mass

398.8900 Da

Monoisotopic Mass

398.17208 Da

IUPAC Name

N-(7-chloro-2-{[({2-oxa-6-azatricyclo[4.2.1.0^{3,7}]nonan-8-yl}methyl)-C-hydroxycarbonimidoyl]oxy}-hexahydro-1H-pyrrolizin-1-yl)ethanimidic acid

Traditional Name

N-{7-chloro-2-[({2-oxa-6-azatricyclo[4.2.1.0^{3,7}]nonan-8-ylmethyl}-C-hydroxycarbonimidoyl)oxy]-hexahydro-1H-pyrrolizin-1-yl}ethanimidic acid

CAS Registry Number

Not Available

SMILES

CC(O)=NC1C(CN2CCC(Cl)C12)OC(O)=NCC1C2CN3CCC(O2)C13

InChI Identifier

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

InChI Key

MEQYZLVMLXTKEV-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 pyrrolizidines. Pyrrolizidines are compounds containing a pyrrolizidine, which is a bicyclic ring system made up of two fused pyrrolidine ring sharing a nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrrolizidines

Sub Class

Not Available

Direct Parent

Pyrrolizidines

Alternative Parents

Substituents

Pyrrolizidine
Para-oxazepine
Morpholine
Oxazinane
N-alkylpyrrolidine
Acetamide
Carbamic acid ester
Pyrrolidine
Oxolane
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Azacycle
Oxacycle
Carboxylic acid derivative
Dialkyl ether
Ether
Organic oxide
Organohalogen compound
Organic nitrogen compound
Organochloride
Organonitrogen compound
Organooxygen compound
Carbonyl group
Organic oxygen compound
Amine
Alkyl halide
Alkyl chloride
Hydrocarbon derivative
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	-3.9	ChemAxon
pKa (Strongest Acidic)	0.15	ChemAxon
pKa (Strongest Basic)	8.06	ChemAxon
Physiological Charge	2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	90.12 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.25 m³·mol⁻¹	ChemAxon
Polarizability	40.84 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

C00025808

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

101316803

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-[({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-ylmethyl}-c-hydroxycarbonimidoyl)oxy]-hexahydro-1h-pyrrolizin-1-yl}ethanimidic acid (NP0270189)

MOL for NP0270189 (n-{7-chloro-2-[({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-ylmethyl}-c-hydroxycarbonimidoyl)oxy]-hexahydro-1h-pyrrolizin-1-yl}ethanimidic acid)

3D MOL for NP0270189 (n-{7-chloro-2-[({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-ylmethyl}-c-hydroxycarbonimidoyl)oxy]-hexahydro-1h-pyrrolizin-1-yl}ethanimidic acid)

3D SDF for NP0270189 (n-{7-chloro-2-[({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-ylmethyl}-c-hydroxycarbonimidoyl)oxy]-hexahydro-1h-pyrrolizin-1-yl}ethanimidic acid)

3D-SDF for NP0270189 (n-{7-chloro-2-[({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-ylmethyl}-c-hydroxycarbonimidoyl)oxy]-hexahydro-1h-pyrrolizin-1-yl}ethanimidic acid)

PDB for NP0270189 (n-{7-chloro-2-[({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-ylmethyl}-c-hydroxycarbonimidoyl)oxy]-hexahydro-1h-pyrrolizin-1-yl}ethanimidic acid)

3D PDB for NP0270189 (n-{7-chloro-2-[({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-ylmethyl}-c-hydroxycarbonimidoyl)oxy]-hexahydro-1h-pyrrolizin-1-yl}ethanimidic acid)

SMILES for NP0270189 (n-{7-chloro-2-[({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-ylmethyl}-c-hydroxycarbonimidoyl)oxy]-hexahydro-1h-pyrrolizin-1-yl}ethanimidic acid)

INCHI for NP0270189 (n-{7-chloro-2-[({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-ylmethyl}-c-hydroxycarbonimidoyl)oxy]-hexahydro-1h-pyrrolizin-1-yl}ethanimidic acid)

Structure for NP0270189 (n-{7-chloro-2-[({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-ylmethyl}-c-hydroxycarbonimidoyl)oxy]-hexahydro-1h-pyrrolizin-1-yl}ethanimidic acid)

3D Structure for NP0270189 (n-{7-chloro-2-[({2-oxa-6-azatricyclo[4.2.1.0³,⁷]nonan-8-ylmethyl}-c-hydroxycarbonimidoyl)oxy]-hexahydro-1h-pyrrolizin-1-yl}ethanimidic acid)