NP-MRD: Showing NP-Card for 5-[(3s,4s,5s)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid (NP0166398)

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Record Information

Version

2.0

Created at

2022-09-03 01:46:33 UTC

Updated at

2022-09-03 01:46:33 UTC

NP-MRD ID

NP0166398

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-[(3s,4s,5s)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid

Description

Acromelic acid A, also known as acromelate a, belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Acromelic acid A is a very strong basic compound (based on its pKa). Acromelic acid A is a potentially toxic compound. 5-[(3s,4s,5s)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid is found in Apis cerana and Clitocybe acromelalga. 5-[(3s,4s,5s)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid was first documented in 1992 (PMID: 1341901). A pyrrolidinecarboxylic acid that is siolated from the poisonous mushroom Clitocybe amoenolens (PMID: 12882485) (PMID: 1359719) (PMID: 1375859) (PMID: 15560485).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 08291401292D          

 25 26  0  0  1  0            999 V2000
   -0.6078    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1298    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6548    1.8053    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3222    2.2902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3222    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    1.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    1.0206    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0367    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4248    0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347    1.0206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    4.3527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275    1.7631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5714    0.7012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    3.1152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    6.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    6.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3957    0.4394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7604   -0.4005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5257    2.6201    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0573    2.6647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0949    1.1497    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  6  0  0  0
  7  4  1  0  0  0  0
  7  5  1  6  0  0  0
  7  6  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  6  1  0  0  0  0
 11  5  2  0  0  0  0
 12  8  1  0  0  0  0
 10 13  1  1  0  0  0
 14  4  1  0  0  0  0
 14 10  1  0  0  0  0
 15  8  2  0  0  0  0
 15 11  1  0  0  0  0
 16  9  2  0  0  0  0
 17  9  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 12  2  0  0  0  0
 21 13  2  0  0  0  0
 22 13  1  0  0  0  0
  6 23  1  1  0  0  0
  7 24  1  1  0  0  0
 10 25  1  6  0  0  0
M  END

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
   -0.5709   -2.5145   -2.4423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4530   -2.2038   -1.5653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832   -3.2107   -0.9415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7099   -0.8029   -1.2065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5430   -0.4921    0.2026 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8455    0.9755    0.5133 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3188    1.2489    0.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0134    1.5041    1.3941 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9217    1.2279   -0.8635 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4824    1.1022    1.8771 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6868    0.0027    2.2750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3067   -0.7617    0.9583 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9438   -0.1789    0.4936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2854    1.1487    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4518    1.7121    0.2340 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3445    0.9561   -0.5233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5907    1.5005   -1.0229 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9026    2.6895   -0.8780 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4606    0.6406   -1.6876 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9927   -0.3293   -0.7348 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8475   -0.8798   -0.2529 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6561   -2.2109   -0.5644 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3026   -3.3260    0.0468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8297   -0.6698   -1.4349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2144   -0.0985   -1.9202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3748   -1.0406    0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3425    1.6576   -0.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7602    1.7696   -1.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3376    1.1886    2.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2614    0.2821    2.7976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1883   -0.7565    2.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2404   -1.8404    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6580    1.8211    1.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7395    2.7534    0.4004 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0332   -0.0270   -1.1417 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4582   -2.8379   -0.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 21  2  0
 21 22  1  0
 21 20  1  0
 20 16  2  0
 16 15  1  0
 15 14  2  0
 16 17  1  0
 17 19  1  0
 17 18  2  0
 12  5  1  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  6  7  1  0
  7  9  1  0
  7  8  2  0
  5  6  1  0
 14 13  1  0
  6 27  1  6
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  1
 22 36  1  0
 15 34  1  0
 14 33  1  0
 19 35  1  0
  5 26  1  1
  4 24  1  0
  4 25  1  0
  3 23  1  0
  9 28  1  0
M  END


  Mrv0541 08291401292D          

 25 26  0  0  1  0            999 V2000
   -0.6078    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    4.3527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1298    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    3.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6548    1.8053    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3222    2.2902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3222    4.7652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    1.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    1.0206    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0367    3.5277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    5.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4248    0.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347    1.0206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    4.3527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275    1.7631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5714    0.7012    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7512    3.1152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0367    6.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6078    6.0027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3957    0.4394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7604   -0.4005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5257    2.6201    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0573    2.6647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0949    1.1497    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  5  1  1  0  0  0  0
  6  3  1  6  0  0  0
  7  4  1  0  0  0  0
  7  5  1  6  0  0  0
  7  6  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  6  1  0  0  0  0
 11  5  2  0  0  0  0
 12  8  1  0  0  0  0
 10 13  1  1  0  0  0
 14  4  1  0  0  0  0
 14 10  1  0  0  0  0
 15  8  2  0  0  0  0
 15 11  1  0  0  0  0
 16  9  2  0  0  0  0
 17  9  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 12  2  0  0  0  0
 21 13  2  0  0  0  0
 22 13  1  0  0  0  0
  6 23  1  1  0  0  0
  7 24  1  1  0  0  0
 10 25  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0166398

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2O7/c16-9(17)3-6-7(4-14-10(6)13(21)22)5-1-2-8(12(19)20)15-11(5)18/h1-2,6-7,10,14H,3-4H2,(H,15,18)(H,16,17)(H,19,20)(H,21,22)/t6-,7+,10-/m0/s1

> <INCHI_KEY>
CWXNEBSQRIECMV-PJKMHFRUSA-N

> <FORMULA>
C13H14N2O7

> <MOLECULAR_WEIGHT>
310.2595

> <EXACT_MASS>
310.080100812

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.390645511404678

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-[(3S,4S,5S)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid

> <ALOGPS_LOGP>
-1.25

> <JCHEM_LOGP>
-2.5135879905554646

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.1296827541572023

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.7132616380723609

> <JCHEM_PKA_STRONGEST_BASIC>
11.926437185303916

> <JCHEM_POLAR_SURFACE_AREA>
157.04999999999998

> <JCHEM_REFRACTIVITY>
70.39059999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(3S,4S,5S)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-AUG-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-AUG-14         0                                  
HETATM    1  C   UNK     0      -1.134   6.585   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.134   8.125   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.242   3.846   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.714   3.370   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.468   5.815   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.222   3.370   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.468   4.275   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.468   8.895   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.387   2.815   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.698   1.905   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.802   6.585   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.468  10.435   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.793   0.659   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -3.238   1.905   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      -3.802   8.125   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       2.851   3.291   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.067   1.309   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -5.136   5.815   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.802  11.205   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.134  11.205   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.739   0.820   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.419  -0.748   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0      -0.981   4.891   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -3.840   4.974   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.177   2.146   0.000  0.00  0.00           H+0
CONECT    1    2    5                                                       
CONECT    2    1    8                                                       
CONECT    3    6    9                                                       
CONECT    4    7   14                                                       
CONECT    5    1    7   11                                                  
CONECT    6    3    7   10   23                                             
CONECT    7    4    5    6   24                                             
CONECT    8    2   12   15                                                  
CONECT    9    3   16   17                                                  
CONECT   10    6   13   14   25                                             
CONECT   11    5   15   18                                                  
CONECT   12    8   19   20                                                  
CONECT   13   10   21   22                                                  
CONECT   14    4   10                                                       
CONECT   15    8   11                                                       
CONECT   16    9                                                            
CONECT   17    9                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22   13                                                            
CONECT   23    6                                                            
CONECT   24    7                                                            
CONECT   25   10                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol

Synonyms

Value	Source
Acromelate a	Generator

Chemical Formula

C₁₃H₁₄N₂O₇

Average Mass

310.2595 Da

Monoisotopic Mass

310.08010 Da

IUPAC Name

5-[(3S,4S,5S)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid

Traditional Name

5-[(3S,4S,5S)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H14N2O7/c16-9(17)3-6-7(4-14-10(6)13(21)22)5-1-2-8(12(19)20)15-11(5)18/h1-2,6-7,10,14H,3-4H2,(H,15,18)(H,16,17)(H,19,20)(H,21,22)/t6-,7+,10-/m0/s1

InChI Key

CWXNEBSQRIECMV-PJKMHFRUSA-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
Apis cerana	LOTUS Database	35616633
Clitocybe acromelalga	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

Macrolide
Benzylether
2-bromophenol
2-halophenol
4-halophenol
4-bromophenol
1-hydroxy-2-unsubstituted benzenoid
Ketal
Bromobenzene
Halobenzene
Phenol
Oxane
Dicarboxylic acid or derivatives
Benzenoid
Monocyclic benzene moiety
Aryl halide
Aryl bromide
Carboxylic acid ester
Secondary alcohol
Hemiacetal
Lactone
Ether
Dialkyl ether
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organobromide
Organohalogen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

macrolide (CHEBI:80717 )
Aplysiatoxins (C16770 )

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	-1.2	ALOGPS
logP	-2.5	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	0.71	ChemAxon
pKa (Strongest Basic)	11.93	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	157.05 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	70.39 m³·mol⁻¹	ChemAxon
Polarizability	28.39 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C19949

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

108086

PDB ID

Not Available

ChEBI ID

134690

Good Scents ID

Not Available

References

General References

Saviuc P, Dematteis M, Mezin P, Danel V, Mallaret M: Toxicity of the Clitocybe amoenolens mushroom in the rat. Vet Hum Toxicol. 2003 Aug;45(4):180-2. [PubMed:12882485 ]
Kwak S, Aizawa H, Ishida M, Shinozaki H: New, potent kainate derivatives: comparison of their affinity for [3H]kainate and [3H]AMPA binding sites. Neurosci Lett. 1992 May 11;139(1):114-7. doi: 10.1016/0304-3940(92)90870-d. [PubMed:1341901 ]
Shinozaki H: [Pharmacology of excitatory amino acid receptors]. Yakubutsu Seishin Kodo. 1992 Apr;12(2):55-65. [PubMed:1359719 ]
Smith AL, McIlhinney RA: Effects of acromelic acid A on the binding of [3H]-kainic acid and [3H]-AMPA to rat brain synaptic plasma membranes. Br J Pharmacol. 1992 Jan;105(1):83-6. doi: 10.1111/j.1476-5381.1992.tb14214.x. [PubMed:1375859 ]
Bessard J, Saviuc P, Chane-Yene Y, Monnet S, Bessard G: Mass spectrometric determination of acromelic acid A from a new poisonous mushroom: Clitocybe amoenolens. J Chromatogr A. 2004 Nov 5;1055(1-2):99-107. doi: 10.1016/j.chroma.2004.08.133. [PubMed:15560485 ]
LOTUS database [Link]

Showing NP-Card for 5-[(3s,4s,5s)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid (NP0166398)

MOL for NP0166398 (5-[(3s,4s,5s)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid)

3D MOL for NP0166398 (5-[(3s,4s,5s)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid)

3D SDF for NP0166398 (5-[(3s,4s,5s)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid)

3D-SDF for NP0166398 (5-[(3s,4s,5s)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid)

PDB for NP0166398 (5-[(3s,4s,5s)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid)

3D PDB for NP0166398 (5-[(3s,4s,5s)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid)

SMILES for NP0166398 (5-[(3s,4s,5s)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid)

INCHI for NP0166398 (5-[(3s,4s,5s)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid)

Structure for NP0166398 (5-[(3s,4s,5s)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid)

3D Structure for NP0166398 (5-[(3s,4s,5s)-5-carboxy-4-(carboxymethyl)pyrrolidin-3-yl]-6-hydroxypyridine-2-carboxylic acid)