NP-MRD: Showing NP-Card for (2r,5r)-2-[(1s,2r)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2s)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid (NP0310986)

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Record Information

Version

2.0

Created at

2022-09-11 06:40:43 UTC

Updated at

2022-09-11 06:40:43 UTC

NP-MRD ID

NP0310986

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,5r)-2-[(1s,2r)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2s)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid

Description

Kaitocephalin belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine. Due to the small amounts of kaitocephalin available, its absolute structure was not determined through chemical degradation. Kaitocephalin is a very strong basic compound (based on its pKa). Glutamate is the most abundant neurotransmitter in the vertebrate nervous system and is involved in learning, memory, and neuroplasticity. (2r,5r)-2-[(1s,2r)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2s)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid is found in Penicillium miczynskii. To form kaitocephalin's pyrrolidine core, a stereoconvergent cyclization reaction was discovered.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05031419202D          

 36 37  0  0  1  0            999 V2000
    1.1270   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022   -8.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4582   -7.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -5.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -7.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -4.9820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7871   -9.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9431   -8.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -6.4032    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0735   -3.2709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6076   -8.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -3.0994    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1528   -6.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9731   -6.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6255   -2.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -3.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4515   -9.8266    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7636   -8.1468    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3284   -4.0556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -7.0706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -4.1974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0925   -9.6541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0116   -2.3148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -6.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3086   -7.2431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4580   -5.8220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3706   -1.8732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4325   -2.8294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6445   -3.2709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174   -2.3148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9053   -5.5447    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8366   -5.9418    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8185   -2.4863    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214   -3.8840    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  1  1  0  0  0  0
  7  5  1  6  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
 10  5  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 18  2  1  0  0  0  0
 18 13  1  1  0  0  0
 18 17  1  6  0  0  0
 19  8  1  0  0  0  0
 20  9  1  0  0  0  0
 11 21  1  1  0  0  0
 10 22  1  6  0  0  0
 22 14  2  0  0  0  0
 23  7  1  0  0  0  0
 23 18  1  0  0  0  0
 24 12  1  0  0  0  0
 13 25  1  6  0  0  0
 14 26  1  4  0  0  0
 27 15  2  0  0  0  0
 28 15  1  0  0  0  0
 29 16  2  0  0  0  0
 30 16  1  0  0  0  0
 31 17  2  0  0  0  0
 32 17  1  0  0  0  0
  7 33  1  1  0  0  0
 10 34  1  6  0  0  0
 11 35  1  1  0  0  0
 13 36  1  6  0  0  0
M  END

     RDKit          3D

 53 54  0  0  0  0  0  0  0  0999 V2000
    3.4371    0.3984   -2.0881 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5366   -0.0930   -1.3090 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6921    0.8262   -1.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8159    0.6575   -1.0015 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5992    1.9284   -2.4036 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2796   -0.1308    0.1769 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4677   -0.6311    0.8000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1334   -0.9638    0.6090 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3683   -2.4258    0.3419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5400   -3.1771   -0.2074 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5808   -2.9445    0.7374 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0796   -0.8750    2.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5699   -1.0510    2.3687 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0996   -0.1019    1.2339 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3768   -0.1080    1.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0662    0.7343    0.1701 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5136    0.4959    0.3813 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4034    1.0853   -0.2902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0514    1.9927   -1.2670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8083    0.8225   -0.0505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2370   -0.0795    0.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5557   -0.3351    1.1569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0763   -1.4746    2.3918 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -7.5410    0.3014    0.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8855    0.0294    0.6788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1452    1.1953   -0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3800    2.0083   -1.4709 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.8099    1.4506   -0.7720 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7274    0.4922   -1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4145    0.7546   -1.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6317   -0.0296   -2.1704 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8337   -0.5999    0.1290 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6092    0.2598   -3.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1440    1.3627   -1.8318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7866   -1.1120   -1.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0936    2.7556   -2.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1752    0.9014    0.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0070    0.0919    1.1603 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6115   -3.3237    1.6965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6643   -1.6585    2.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3290    0.1265    2.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2778   -2.0642    2.0689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2418   -0.7132    3.3467 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5327    0.8829    1.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7569   -1.1750    1.1180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7425    0.2246    2.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9393    1.8199    0.4489 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5239    2.8884   -1.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4616   -0.5870    1.5050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1234   -0.6370    1.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5020    2.1624   -1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0553   -0.9418   -2.0905 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3935   -1.4159   -0.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
  2  6  1  0
  6  7  1  0
  6  8  1  0
  8 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  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 26 28  2  0
 16 29  1  0
 29 31  1  0
 29 30  2  0
 14 32  1  0
  8  9  1  1
  9 11  1  0
  9 10  2  0
 32  8  1  0
 28 20  1  0
  2 35  1  6
  1 33  1  0
  1 34  1  0
  5 36  1  0
  6 37  1  1
  7 38  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  1
 15 45  1  0
 15 46  1  0
 16 47  1  1
 19 48  1  0
 21 49  1  0
 25 50  1  0
 28 51  1  0
 31 52  1  0
 32 53  1  0
 11 39  1  0
M  END


  Mrv0541 05031419202D          

 36 37  0  0  1  0            999 V2000
    1.1270   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3022   -8.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4582   -7.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1830   -5.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6377   -7.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -4.9820    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7871   -9.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9431   -8.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1526   -6.4032    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0735   -3.2709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6076   -8.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -3.0994    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1528   -6.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9731   -6.4894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6255   -2.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -3.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4515   -9.8266    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7636   -8.1468    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3284   -4.0556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -7.0706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -4.1974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0925   -9.6541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0116   -2.3148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884   -6.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3086   -7.2431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4580   -5.8220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3706   -1.8732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4325   -2.8294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6445   -3.2709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4174   -2.3148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9053   -5.5447    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8366   -5.9418    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8185   -2.4863    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214   -3.8840    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  3  2  0  0  0  0
  6  4  1  0  0  0  0
  7  1  1  0  0  0  0
  7  5  1  6  0  0  0
  8  3  1  0  0  0  0
  9  4  2  0  0  0  0
 10  5  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 18  2  1  0  0  0  0
 18 13  1  1  0  0  0
 18 17  1  6  0  0  0
 19  8  1  0  0  0  0
 20  9  1  0  0  0  0
 11 21  1  1  0  0  0
 10 22  1  6  0  0  0
 22 14  2  0  0  0  0
 23  7  1  0  0  0  0
 23 18  1  0  0  0  0
 24 12  1  0  0  0  0
 13 25  1  6  0  0  0
 14 26  1  4  0  0  0
 27 15  2  0  0  0  0
 28 15  1  0  0  0  0
 29 16  2  0  0  0  0
 30 16  1  0  0  0  0
 31 17  2  0  0  0  0
 32 17  1  0  0  0  0
  7 33  1  1  0  0  0
 10 34  1  6  0  0  0
 11 35  1  1  0  0  0
 13 36  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0310986

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](N)(C(O)=O)[C@]([H])(O)[C@]1(CC[C@]([H])(C[C@]([H])(N=C(O)C2=CC(Cl)=C(O)C(Cl)=C2)C(O)=O)N1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H21Cl2N3O9/c19-8-3-6(4-9(20)12(8)24)14(26)22-10(15(27)28)5-7-1-2-18(23-7,17(31)32)13(25)11(21)16(29)30/h3-4,7,10-11,13,23-25H,1-2,5,21H2,(H,22,26)(H,27,28)(H,29,30)(H,31,32)/t7-,10+,11-,13+,18-/m1/s1

> <INCHI_KEY>
AJQRDRIPQOAJCM-BWOKQULHSA-N

> <FORMULA>
C18H21Cl2N3O9

> <MOLECULAR_WEIGHT>
494.28

> <EXACT_MASS>
493.065484699

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
44.53239203267617

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5R)-2-[(1S,2R)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2S)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid

> <ALOGPS_LOGP>
-0.89

> <JCHEM_LOGP>
-4.182561972129911

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
1.7580417604582994

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8940377768463144

> <JCHEM_PKA_STRONGEST_BASIC>
11.353543235774486

> <JCHEM_POLAR_SURFACE_AREA>
222.99999999999997

> <JCHEM_REFRACTIVITY>
108.31299999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5R)-2-[(1S,2R)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2S)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   20 Cl   UNK     0       0.000   0.000   0.000  0.00  0.00          Cl+0
HETATM   21  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   22  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    2    7                                                       
CONECT    2    1   18                                                       
CONECT    3    6    8                                                       
CONECT    4    6    9                                                       
CONECT    5    7   10                                                       
CONECT    6    3    4   14                                                  
CONECT    7    1    5   23   33                                             
CONECT    8    3   12   19                                                  
CONECT    9    4   12   20                                                  
CONECT   10    5   15   22   34                                             
CONECT   11   13   16   21   35                                             
CONECT   12    8    9   24                                                  
CONECT   13   11   18   25   36                                             
CONECT   14    6   22   26                                                  
CONECT   15   10   27   28                                                  
CONECT   16   11   29   30                                                  
CONECT   17   18   31   32                                                  
CONECT   18    2   13   17   23                                             
CONECT   19    8                                                            
CONECT   20    9                                                            
CONECT   21   11                                                            
CONECT   22   10   14                                                       
CONECT   23    7   18                                                       
CONECT   24   12                                                            
CONECT   25   13                                                            
CONECT   26   14                                                            
CONECT   27   15                                                            
CONECT   28   15                                                            
CONECT   29   16                                                            
CONECT   30   16                                                            
CONECT   31   17                                                            
CONECT   32   17                                                            
CONECT   33    7                                                            
CONECT   34   10                                                            
CONECT   35   11                                                            
CONECT   36   13                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   74    0
END

View in JSmol

Synonyms

Value	Source
(2R,5R)-2-[(1S,2R)-2-Amino-2-carboxy-1-hydroxyethyl]-5-[(2S)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylate	Generator

Chemical Formula

C₁₈H₂₁Cl₂N₃O₉

Average Mass

494.2800 Da

Monoisotopic Mass

493.06548 Da

IUPAC Name

(2R,5R)-2-[(1S,2R)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2S)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid

Traditional Name

(2R,5R)-2-[(1S,2R)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2S)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@](N)(C(O)=O)[C@]([H])(O)[C@]1(CC[C@]([H])(C[C@]([H])(N=C(O)C2=CC(Cl)=C(O)C(Cl)=C2)C(O)=O)N1)C(O)=O

InChI Identifier

InChI=1S/C18H21Cl2N3O9/c19-8-3-6(4-9(20)12(8)24)14(26)22-10(15(27)28)5-7-1-2-18(23-7,17(31)32)13(25)11(21)16(29)30/h3-4,7,10-11,13,23-25H,1-2,5,21H2,(H,22,26)(H,27,28)(H,29,30)(H,31,32)/t7-,10+,11-,13+,18-/m1/s1

InChI Key

AJQRDRIPQOAJCM-BWOKQULHSA-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
Penicillium miczynskii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hippuric acids. Hippuric acids are compounds containing hippuric acid, which consists of a of a benzoyl group linked to the N-terminal of a glycine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Hippuric acids

Alternative Parents

Substituents

N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Hippuric acid
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
D-alpha-amino acid
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Tricarboxylic acid or derivatives
2-chlorophenol
1,3-dichlorobenzene
2-halophenol
Pyrrolidine carboxylic acid or derivatives
Pyrrolidine carboxylic acid
Benzoyl
Beta-hydroxy acid
Halobenzene
Phenol
Chlorobenzene
Hydroxy acid
Aryl halide
Aryl chloride
Pyrrolidine
Amino acid or derivatives
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Azacycle
Carboxylic acid derivative
Secondary amine
Carboxylic acid
Secondary aliphatic amine
Organoheterocyclic compound
Organohalogen compound
Amine
Alcohol
Organic oxygen compound
Carbonyl group
Primary amine
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Organooxygen compound
Primary aliphatic amine
Organonitrogen compound
Organochloride
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	-0.89	ALOGPS
logP	-4.2	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	0.89	ChemAxon
pKa (Strongest Basic)	11.35	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	223 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	108.31 m³·mol⁻¹	ChemAxon
Polarizability	44.53 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	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

Kaitocephalin

METLIN ID

Not Available

PubChem Compound

11329395

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,5r)-2-[(1s,2r)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2s)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid (NP0310986)

MOL for NP0310986 ((2r,5r)-2-[(1s,2r)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2s)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid)

3D MOL for NP0310986 ((2r,5r)-2-[(1s,2r)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2s)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid)

3D SDF for NP0310986 ((2r,5r)-2-[(1s,2r)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2s)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid)

3D-SDF for NP0310986 ((2r,5r)-2-[(1s,2r)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2s)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid)

PDB for NP0310986 ((2r,5r)-2-[(1s,2r)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2s)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid)

3D PDB for NP0310986 ((2r,5r)-2-[(1s,2r)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2s)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid)

SMILES for NP0310986 ((2r,5r)-2-[(1s,2r)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2s)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid)

INCHI for NP0310986 ((2r,5r)-2-[(1s,2r)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2s)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid)

Structure for NP0310986 ((2r,5r)-2-[(1s,2r)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2s)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid)

3D Structure for NP0310986 ((2r,5r)-2-[(1s,2r)-2-amino-2-carboxy-1-hydroxyethyl]-5-[(2s)-2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl]pyrrolidine-2-carboxylic acid)