NP-MRD: Showing NP-Card for Pyrrolysine (NP0004186)

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Record Information

Version

2.0

Created at

2020-12-09 01:40:41 UTC

Updated at

2021-07-15 16:48:29 UTC

NP-MRD ID

NP0004186

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pyrrolysine

Provided By

NPAtlas

Description

Pyrrolysine belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Pyrrolysine is found in Unknown-fungus sp. Pyrrolysine was first documented in 2002 (PMID: 12029132). Based on a literature review a small amount of articles have been published on pyrrolysine (PMID: 34335502) (PMID: 34168131) (PMID: 34149676).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118043D          

 39 39  0  0  0  0            999 V2000
    4.7905    1.0098   -0.8854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8804   -0.0194   -0.2958 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4592   -0.7031    0.9180 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0792    0.1827    2.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0959    0.8990    1.7036 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6592    0.6392    0.3741 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5113   -0.3273    0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0585   -0.7969    1.4426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9362   -0.7119   -0.8619 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620   -1.6278   -0.9137 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3826   -1.0786   -0.1714 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7464    0.2000   -0.8386 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9046    0.9431   -0.2841 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2193    0.2165   -0.2932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1927   -1.0056    0.4822 N   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2260    1.1172    0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4163    2.2419   -0.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9302    0.7330    1.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3861    2.0376   -0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8013    0.9717   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8317    0.9436   -0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635   -0.7438   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5570   -0.8407    0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362   -1.6841    1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917    0.2110    3.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4097    1.5865   -0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496   -0.2961   -1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1048   -2.6214   -0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4209   -1.8152   -1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1756   -1.8654   -0.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432   -0.9989    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8749    0.0262   -1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8424    0.8716   -0.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6938    1.2784    0.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705    1.9129   -0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5381   -0.0420   -1.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6483   -0.8911    1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1622   -1.2746    0.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3522    1.3221    2.1056 H   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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  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
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  6  2  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  2 22  1  6  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  4 25  1  0  0  0  0
  6 26  1  6  0  0  0
  9 27  1  0  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 13 34  1  0  0  0  0
 13 35  1  0  0  0  0
 14 36  1  6  0  0  0
 15 37  1  0  0  0  0
 15 38  1  0  0  0  0
 18 39  1  0  0  0  0
M  END

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    4.7905    1.0098   -0.8854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8804   -0.0194   -0.2958 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4592   -0.7031    0.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792    0.1827    2.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0959    0.8990    1.7036 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6592    0.6392    0.3741 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5113   -0.3273    0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0585   -0.7969    1.4426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9362   -0.7119   -0.8619 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620   -1.6278   -0.9137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3826   -1.0786   -0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7464    0.2000   -0.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9046    0.9431   -0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2193    0.2165   -0.2932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1927   -1.0056    0.4822 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2260    1.1172    0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4163    2.2419   -0.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9302    0.7330    1.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3861    2.0376   -0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8013    0.9717   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8317    0.9436   -0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635   -0.7438   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5570   -0.8407    0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362   -1.6841    1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917    0.2110    3.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4097    1.5865   -0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496   -0.2961   -1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1048   -2.6214   -0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4209   -1.8152   -1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1756   -1.8654   -0.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432   -0.9989    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8749    0.0262   -1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8424    0.8716   -0.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6938    1.2784    0.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705    1.9129   -0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5381   -0.0420   -1.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6483   -0.8911    1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1622   -1.2746    0.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3522    1.3221    2.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
  6  2  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  6
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  6
 15 37  1  0
 15 38  1  0
 18 39  1  0
M  END


  Mrv1652306242118043D          

 39 39  0  0  0  0            999 V2000
    4.7905    1.0098   -0.8854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8804   -0.0194   -0.2958 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4592   -0.7031    0.9180 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0792    0.1827    2.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0959    0.8990    1.7036 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6592    0.6392    0.3741 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5113   -0.3273    0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0585   -0.7969    1.4426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9362   -0.7119   -0.8619 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620   -1.6278   -0.9137 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3826   -1.0786   -0.1714 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7464    0.2000   -0.8386 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9046    0.9431   -0.2841 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2193    0.2165   -0.2932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1927   -1.0056    0.4822 N   0  0  1  0  0  0  0  0  0  0  0  0
   -5.2260    1.1172    0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4163    2.2419   -0.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9302    0.7330    1.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3861    2.0376   -0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8013    0.9717   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8317    0.9436   -0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635   -0.7438   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5570   -0.8407    0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362   -1.6841    1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917    0.2110    3.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4097    1.5865   -0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496   -0.2961   -1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1048   -2.6214   -0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4209   -1.8152   -1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1756   -1.8654   -0.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432   -0.9989    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8749    0.0262   -1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8424    0.8716   -0.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6938    1.2784    0.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705    1.9129   -0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5381   -0.0420   -1.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6483   -0.8911    1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1622   -1.2746    0.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3522    1.3221    2.1056 H   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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  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
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  6  2  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  2 22  1  6  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  4 25  1  0  0  0  0
  6 26  1  6  0  0  0
  9 27  1  0  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
 11 30  1  0  0  0  0
 11 31  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
 13 34  1  0  0  0  0
 13 35  1  0  0  0  0
 14 36  1  6  0  0  0
 15 37  1  0  0  0  0
 15 38  1  0  0  0  0
 18 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0004186

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@]([H])(N([H])[H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])N([H])C(=O)[C@@]1([H])N=C([H])C([H])([H])[C@]1([H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C12H21N3O3/c1-8-5-7-14-10(8)11(16)15-6-3-2-4-9(13)12(17)18/h7-10H,2-6,13H2,1H3,(H,15,16)(H,17,18)/t8-,9+,10-/m0/s1

> <INCHI_KEY>
ZFOMKMMPBOQKMC-UHFFFAOYSA-N

> <FORMULA>
C12H21N3O3

> <MOLECULAR_WEIGHT>
255.318

> <EXACT_MASS>
255.158291548

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.236878845805524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-6-{[(2S,3S)-3-methyl-3,4-dihydro-2H-pyrrol-2-yl]formamido}hexanoic acid

> <ALOGPS_LOGP>
-2.82

> <JCHEM_LOGP>
-2.798077338479738

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.429015454324205

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8657093366095405

> <JCHEM_PKA_STRONGEST_BASIC>
9.526535758386729

> <JCHEM_POLAR_SURFACE_AREA>
104.78000000000002

> <JCHEM_REFRACTIVITY>
66.47850000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.57e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-amino-6-{[(2S,3S)-3-methyl-3,4-dihydro-2H-pyrrol-2-yl]formamido}hexanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    4.7905    1.0098   -0.8854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8804   -0.0194   -0.2958 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4592   -0.7031    0.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792    0.1827    2.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0959    0.8990    1.7036 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6592    0.6392    0.3741 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5113   -0.3273    0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0585   -0.7969    1.4426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9362   -0.7119   -0.8619 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620   -1.6278   -0.9137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3826   -1.0786   -0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7464    0.2000   -0.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9046    0.9431   -0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2193    0.2165   -0.2932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1927   -1.0056    0.4822 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2260    1.1172    0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4163    2.2419   -0.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9302    0.7330    1.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3861    2.0376   -0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8013    0.9717   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8317    0.9436   -0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635   -0.7438   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5570   -0.8407    0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362   -1.6841    1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917    0.2110    3.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4097    1.5865   -0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496   -0.2961   -1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1048   -2.6214   -0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4209   -1.8152   -1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1756   -1.8654   -0.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432   -0.9989    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8749    0.0262   -1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8424    0.8716   -0.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6938    1.2784    0.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705    1.9129   -0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5381   -0.0420   -1.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6483   -0.8911    1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1622   -1.2746    0.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3522    1.3221    2.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
  6  2  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  6
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  6
 15 37  1  0
 15 38  1  0
 18 39  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.790   1.010  -0.885  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.880  -0.019  -0.296  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.459  -0.703   0.918  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.079   0.183   2.034  0.00  0.00           C+0
HETATM    5  N   UNK     0       3.096   0.899   1.704  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.659   0.639   0.374  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.511  -0.327   0.364  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.059  -0.797   1.443  0.00  0.00           O+0
HETATM    9  N   UNK     0       0.936  -0.712  -0.862  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.162  -1.628  -0.914  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.383  -1.079  -0.171  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.746   0.200  -0.839  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.905   0.943  -0.284  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.219   0.217  -0.293  0.00  0.00           C+0
HETATM   15  N   UNK     0      -4.193  -1.006   0.482  0.00  0.00           N+0
HETATM   16  C   UNK     0      -5.226   1.117   0.319  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.416   2.242  -0.196  0.00  0.00           O+0
HETATM   18  O   UNK     0      -5.930   0.733   1.417  0.00  0.00           O+0
HETATM   19  H   UNK     0       4.386   2.038  -0.653  0.00  0.00           H+0
HETATM   20  H   UNK     0       4.801   0.972  -2.012  0.00  0.00           H+0
HETATM   21  H   UNK     0       5.832   0.944  -0.570  0.00  0.00           H+0
HETATM   22  H   UNK     0       3.563  -0.744  -1.063  0.00  0.00           H+0
HETATM   23  H   UNK     0       5.557  -0.841   0.836  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.936  -1.684   1.068  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.592   0.211   3.025  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.410   1.587  -0.101  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.350  -0.296  -1.738  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.105  -2.621  -0.499  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.421  -1.815  -1.986  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.176  -1.865  -0.284  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.143  -0.999   0.882  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.875   0.026  -1.929  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.842   0.872  -0.742  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.694   1.278   0.766  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.970   1.913  -0.853  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.538  -0.042  -1.339  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.648  -0.891   1.367  0.00  0.00           H+0
HETATM   38  H   UNK     0      -5.162  -1.275   0.769  0.00  0.00           H+0
HETATM   39  H   UNK     0      -6.352   1.322   2.106  0.00  0.00           H+0
CONECT    1    2   19   20   21                                             
CONECT    2    1    3    6   22                                             
CONECT    3    2    4   23   24                                             
CONECT    4    3    5   25                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    2   26                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   27                                                  
CONECT   10    9   11   28   29                                             
CONECT   11   10   12   30   31                                             
CONECT   12   11   13   32   33                                             
CONECT   13   12   14   34   35                                             
CONECT   14   13   15   16   36                                             
CONECT   15   14   37   38                                                  
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   39                                                       
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    2                                                            
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    4                                                            
CONECT   26    6                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   11                                                            
CONECT   32   12                                                            
CONECT   33   12                                                            
CONECT   34   13                                                            
CONECT   35   13                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   15                                                            
CONECT   39   18                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   78    0
END

RDKit          3D

39 39  0  0  0  0  0  0  0  0999 V2000
    4.7905    1.0098   -0.8854 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8804   -0.0194   -0.2958 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4592   -0.7031    0.9180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792    0.1827    2.0337 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0959    0.8990    1.7036 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6592    0.6392    0.3741 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5113   -0.3273    0.3636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0585   -0.7969    1.4426 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9362   -0.7119   -0.8619 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620   -1.6278   -0.9137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3826   -1.0786   -0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7464    0.2000   -0.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9046    0.9431   -0.2841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2193    0.2165   -0.2932 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1927   -1.0056    0.4822 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2260    1.1172    0.3187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4163    2.2419   -0.1964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9302    0.7330    1.4168 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3861    2.0376   -0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8013    0.9717   -2.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8317    0.9436   -0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5635   -0.7438   -1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5570   -0.8407    0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9362   -1.6841    1.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917    0.2110    3.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4097    1.5865   -0.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3496   -0.2961   -1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1048   -2.6214   -0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4209   -1.8152   -1.9864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1756   -1.8654   -0.2842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1432   -0.9989    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8749    0.0262   -1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8424    0.8716   -0.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6938    1.2784    0.7663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9705    1.9129   -0.8530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5381   -0.0420   -1.3386 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6483   -0.8911    1.3667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1622   -1.2746    0.7693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3522    1.3221    2.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
  6  2  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  6
  3 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  6
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  6
 15 37  1  0
 15 38  1  0
 18 39  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₂H₂₁N₃O₃

Average Mass

255.3180 Da

Monoisotopic Mass

255.15829 Da

IUPAC Name

(2R)-2-amino-6-{[(2S,3S)-3-methyl-3,4-dihydro-2H-pyrrol-2-yl]formamido}hexanoic acid

Traditional Name

(2R)-2-amino-6-{[(2S,3S)-3-methyl-3,4-dihydro-2H-pyrrol-2-yl]formamido}hexanoic acid

CAS Registry Number

Not Available

SMILES

CC1CC=NC1C(=O)NCCCCC(N)C(O)=O

InChI Identifier

InChI=1S/C12H21N3O3/c1-8-5-7-14-10(8)11(16)15-6-3-2-4-9(13)12(17)18/h7-10H,2-6,13H2,1H3,(H,15,16)(H,17,18)

InChI Key

ZFOMKMMPBOQKMC-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Unknown-fungus sp.	NPAtlas	12029132

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids

Alternative Parents

Substituents

Alpha-amino acid
Pyrroline carboxylic acid or derivatives
Medium-chain fatty acid
Amino fatty acid
Heterocyclic fatty acid
Fatty acid
Fatty acyl
Pyrroline
Carboxamide group
Secondary carboxylic acid amide
Amino acid
Propargyl-type 1,3-dipolar organic compound
Organoheterocyclic compound
Azacycle
Organic 1,3-dipolar compound
Carboxylic acid
Monocarboxylic acid or derivatives
Amine
Organooxygen compound
Organonitrogen compound
Primary amine
Primary aliphatic amine
Imine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-2.8	ALOGPS
logP	-2.8	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	9.53	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.78 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	66.48 m³·mol⁻¹	ChemAxon
Polarizability	27.24 Å³	ChemAxon
Number of Rings	1	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

NPAtlas ID

NPA014850

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10619226

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pyrrolysine

METLIN ID

Not Available

PubChem Compound

21873141

PDB ID

Not Available

ChEBI ID

91273

Good Scents ID

Not Available

References

General References

Hao B, Gong W, Ferguson TK, James CM, Krzycki JA, Chan MK: A new UAG-encoded residue in the structure of a methanogen methyltransferase. Science. 2002 May 24;296(5572):1462-6. doi: 10.1126/science.1069556. [PubMed:12029132 ]
Kivenson V, Paul BG, Valentine DL: An Ecological Basis for Dual Genetic Code Expansion in Marine Deltaproteobacteria. Front Microbiol. 2021 Jul 14;12:680620. doi: 10.3389/fmicb.2021.680620. eCollection 2021. [PubMed:34335502 ]
Ho JML, Miller CA, Smith KA, Mattia JR, Bennett MR: Improved pyrrolysine biosynthesis through phage assisted non-continuous directed evolution of the complete pathway. Nat Commun. 2021 Jun 24;12(1):3914. doi: 10.1038/s41467-021-24183-9. [PubMed:34168131 ]
De Lise F, Strazzulli A, Iacono R, Curci N, Di Fenza M, Maurelli L, Moracci M, Cobucci-Ponzano B: Programmed Deviations of Ribosomes From Standard Decoding in Archaea. Front Microbiol. 2021 Jun 4;12:688061. doi: 10.3389/fmicb.2021.688061. eCollection 2021. [PubMed:34149676 ]

Showing NP-Card for Pyrrolysine (NP0004186)

MOL for NP0004186 (Pyrrolysine)

3D MOL for NP0004186 (Pyrrolysine)

3D SDF for NP0004186 (Pyrrolysine)

3D-SDF for NP0004186 (Pyrrolysine)

PDB for NP0004186 (Pyrrolysine)

3D PDB for NP0004186 (Pyrrolysine)

SMILES for NP0004186 (Pyrrolysine)

INCHI for NP0004186 (Pyrrolysine)

Structure for NP0004186 (Pyrrolysine)

3D Structure for NP0004186 (Pyrrolysine)