NP-MRD: Showing NP-Card for 2-(2-amino-2-carboxy-1-hydroxyethyl)-5-(2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl)pyrrolidine-2-carboxylic acid (NP0325688)

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Record Information

Version

2.0

Created at

2022-09-12 06:37:48 UTC

Updated at

2022-09-12 06:37:49 UTC

NP-MRD ID

NP0325688

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Alpha-Amino-alpha'-(3,5-dichloro-4-hydroxybenzoylamino)-beta-hydroxy-2-carboxy-2,5-pyrrolidinedipropionic acid 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. 2-(2-amino-2-carboxy-1-hydroxyethyl)-5-(2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl)pyrrolidine-2-carboxylic acid is found in Penicillium miczynskii. Based on a literature review very few articles have been published on alpha-Amino-alpha'-(3,5-dichloro-4-hydroxybenzoylamino)-beta-hydroxy-2-carboxy-2,5-pyrrolidinedipropionic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122208382D          

 32 33  0  0  0  0            999 V2000
    0.8995   -4.0556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6445   -3.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1966   -2.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9416   -1.8732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0035   -2.8294    0.0000 O   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
   -0.4174   -2.3148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2665   -3.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0735   -3.2709    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
   -0.0470   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6119   -5.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4324   -5.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9173   -6.2307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7378   -6.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0733   -5.3908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2227   -6.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8871   -7.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3721   -8.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0365   -8.9867    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925   -8.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6775   -8.8142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5281   -7.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3486   -7.3069    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0432   -6.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7679   -4.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5884   -4.7233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2830   -4.1421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819   -4.1974    0.0000 N   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  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 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
 17 16  1  4  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 20 28  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 14 32  1  0  0  0  0
  8 32  1  0  0  0  0
M  END

     RDKit          3D

 53 54  0  0  0  0  0  0  0  0999 V2000
   -5.2783   -0.0460   -0.6370 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6823    1.2525   -0.5643 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7279    2.1340    0.0929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4228    3.3294    0.2631 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9531    1.6520    0.4853 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4151    1.2949    0.2298 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6302    0.9147    1.5636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2879    0.4568   -0.3697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0730    0.7476   -1.8024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9157    1.1759   -2.1396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9964    0.5999   -2.8089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6574   -1.0142   -0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3318   -1.6127    0.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9610   -0.4789    1.2071 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2578   -0.6641    1.9976 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5554   -0.8712    1.2470 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9086    0.1704    0.4067 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8009    0.7276   -0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4029    1.8948   -0.9620 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2143    0.4172   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8299   -0.6382    0.2707 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1768   -0.8750    0.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8815   -2.2448    0.9257 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.9895   -0.0836   -0.6639 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3557   -0.3467   -0.8110 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3947    0.9830   -1.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3918    2.0204   -2.2851 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0501    1.2220   -1.1291 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5899   -2.2002    0.5776 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9400   -2.3545   -0.6120 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2181   -3.3259    1.2990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0622    0.6637    0.3932 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1568   -0.5346   -1.5450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2438   -0.1104   -0.2624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5088    1.6821   -1.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7885    2.2069    0.4788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0608    2.3436    0.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5422    0.5619    1.7105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871   -0.3291   -3.1902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8967   -1.4439   -1.2283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3972   -1.2070    0.5357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7140   -1.7077   -0.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4968   -2.5652    0.7909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8095   -0.4422    1.9587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1336   -1.5240    2.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4075    0.2282    2.6397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3152   -0.9618    2.0876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2397    2.7545   -0.4679 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2545   -1.3140    0.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7308   -1.1430   -0.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6555    2.0740   -1.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7941   -4.1561    1.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2916    0.6873   -0.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  6
  9 11  1  0
  9 10  2  0
  2  3  1  0
  3  5  1  0
  3  4  2  0
 32  8  1  0
 28 20  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  6
  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
  5 36  1  0
M  END


  Mrv1652309122208382D          

 32 33  0  0  0  0            999 V2000
    0.8995   -4.0556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6445   -3.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1966   -2.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9416   -1.8732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0035   -2.8294    0.0000 O   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
   -0.4174   -2.3148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2665   -3.0994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0735   -3.2709    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
   -0.0470   -4.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -4.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6119   -5.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4324   -5.5632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9173   -6.2307    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7378   -6.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0733   -5.3908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2227   -6.8119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8871   -7.5656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3721   -8.2330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0365   -8.9867    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925   -8.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6775   -8.8142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5281   -7.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3486   -7.3069    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -5.0432   -6.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7679   -4.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5884   -4.7233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2830   -4.1421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819   -4.1974    0.0000 N   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  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  8 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
 17 16  1  4  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 20 28  1  0  0  0  0
 16 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 14 32  1  0  0  0  0
  8 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0325688

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(C(O)C1(CCC(CC(N=C(O)C2=CC(Cl)=C(O)C(Cl)=C2)C(O)=O)N1)C(O)=O)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)

> <INCHI_KEY>
AJQRDRIPQOAJCM-UHFFFAOYSA-N

> <FORMULA>
C18H21Cl2N3O9

> <MOLECULAR_WEIGHT>
494.28

> <EXACT_MASS>
493.0654847

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
44.846563465711554

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-4.177590543849413

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
1.758019174196467

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8940325094771473

> <JCHEM_PKA_STRONGEST_BASIC>
10.772436996176046

> <JCHEM_POLAR_SURFACE_AREA>
222.99999999999997

> <JCHEM_REFRACTIVITY>
108.31299999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  N   UNK     0       1.679  -7.570   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       1.203  -6.106   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.234  -4.961   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.758  -3.497   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.740  -5.281   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.303  -5.786   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.779  -4.321   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.364  -5.786   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.870  -6.106   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.888  -4.321   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.088  -7.835   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.564  -9.300   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.104  -9.300   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.009 -10.546   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.540 -10.385   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -5.446 -11.631   0.000  0.00  0.00           N+0
HETATM   18  C   UNK     0      -6.977 -11.470   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -7.604 -10.063   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -7.882 -12.716   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -7.256 -14.122   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.161 -15.368   0.000  0.00  0.00           C+0
HETATM   23 Cl   UNK     0      -7.535 -16.775   0.000  0.00  0.00          Cl+0
HETATM   24  C   UNK     0      -9.693 -15.207   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -10.598 -16.453   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -10.319 -13.800   0.000  0.00  0.00           C+0
HETATM   27 Cl   UNK     0     -11.851 -13.639   0.000  0.00  0.00          Cl+0
HETATM   28  C   UNK     0      -9.414 -12.555   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.167  -8.978   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -6.698  -8.817   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -4.262  -7.732   0.000  0.00  0.00           O+0
HETATM   32  N   UNK     0      -2.580  -7.835   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   12   32                                             
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   32                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   29                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   20                                                       
CONECT   29   16   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   14    8                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   66    0
END

View in JSmol

Synonyms

Value	Source
a-Amino-alpha'-(3,5-dichloro-4-hydroxybenzoylamino)-b-hydroxy-2-carboxy-2,5-pyrrolidinedipropionate	Generator
a-Amino-alpha'-(3,5-dichloro-4-hydroxybenzoylamino)-b-hydroxy-2-carboxy-2,5-pyrrolidinedipropionic acid	Generator
alpha-Amino-alpha'-(3,5-dichloro-4-hydroxybenzoylamino)-beta-hydroxy-2-carboxy-2,5-pyrrolidinedipropionate	Generator
Α-amino-alpha'-(3,5-dichloro-4-hydroxybenzoylamino)-β-hydroxy-2-carboxy-2,5-pyrrolidinedipropionate	Generator
Α-amino-alpha'-(3,5-dichloro-4-hydroxybenzoylamino)-β-hydroxy-2-carboxy-2,5-pyrrolidinedipropionic acid	Generator

Chemical Formula

C₁₈H₂₁Cl₂N₃O₉

Average Mass

494.2800 Da

Monoisotopic Mass

493.06548 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

NC(C(O)C1(CCC(CC(N=C(O)C2=CC(Cl)=C(O)C(Cl)=C2)C(O)=O)N1)C(O)=O)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)

InChI Key

AJQRDRIPQOAJCM-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
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
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Tricarboxylic acid or derivatives
2-chlorophenol
Benzoyl
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
2-halophenol
1,3-dichlorobenzene
Phenol
Halobenzene
Beta-hydroxy acid
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	-4.2	ChemAxon
pKa (Strongest Acidic)	0.89	ChemAxon
pKa (Strongest Basic)	10.77	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	44.85 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

7981524

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9805764

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(2-amino-2-carboxy-1-hydroxyethyl)-5-(2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl)pyrrolidine-2-carboxylic acid (NP0325688)

MOL for NP0325688 (2-(2-amino-2-carboxy-1-hydroxyethyl)-5-(2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl)pyrrolidine-2-carboxylic acid)

3D MOL for NP0325688 (2-(2-amino-2-carboxy-1-hydroxyethyl)-5-(2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl)pyrrolidine-2-carboxylic acid)

3D SDF for NP0325688 (2-(2-amino-2-carboxy-1-hydroxyethyl)-5-(2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl)pyrrolidine-2-carboxylic acid)

3D-SDF for NP0325688 (2-(2-amino-2-carboxy-1-hydroxyethyl)-5-(2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl)pyrrolidine-2-carboxylic acid)

PDB for NP0325688 (2-(2-amino-2-carboxy-1-hydroxyethyl)-5-(2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl)pyrrolidine-2-carboxylic acid)

3D PDB for NP0325688 (2-(2-amino-2-carboxy-1-hydroxyethyl)-5-(2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl)pyrrolidine-2-carboxylic acid)

SMILES for NP0325688 (2-(2-amino-2-carboxy-1-hydroxyethyl)-5-(2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl)pyrrolidine-2-carboxylic acid)

INCHI for NP0325688 (2-(2-amino-2-carboxy-1-hydroxyethyl)-5-(2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl)pyrrolidine-2-carboxylic acid)

Structure for NP0325688 (2-(2-amino-2-carboxy-1-hydroxyethyl)-5-(2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl)pyrrolidine-2-carboxylic acid)

3D Structure for NP0325688 (2-(2-amino-2-carboxy-1-hydroxyethyl)-5-(2-carboxy-2-{[(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylidene]amino}ethyl)pyrrolidine-2-carboxylic acid)