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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-15 18:04:04 UTC

Update Date

2021-09-14 15:46:06 UTC

HMDB ID

HMDB0060617

Secondary Accession Numbers

HMDB60617

Metabolite Identification

Common Name

Penicilloic acid

Description

Penicilloic acid, also known as penicilloate, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Penicilloic acid is any of several acids which are obtained from the penicillins by the hydrolytic opening of the lactam ring (as by the action of a beta-lactamase). Penicilloic acid is a very strong basic compound (based on its pKa). The major antigenic determinant of penicillin hypersensitivity is its metabolite, penicilloic acid, which reacts with proteins and serves as a hapten to cause an immune reaction. To determine whether treatment with a β-lactam is safe when an allergy is noted, patient history regarding severity of previous reaction is essential. Among patients with mononucleosis who are treated with ampicillin, the incidence of maculopapular rash approaches 100 percent. Cross-allergic reactions occur among the β-lactam antibiotics. Approximately five percent of patients have some kind of reaction, ranging from maculopapular rash (the most common rash seen with ampicillin hypersensitivity) to angioedema (marked swelling of the lips, tongue, and periorbital area) and anaphylaxis. Hypersensitivity is the most important adverse effect of the penicillins.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0060617
     RDKit          3D
Penicilloic acid
 44 45  0  0  0  0  0  0  0  0999 V2000
    3.9018    2.1088    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7482    1.3046   -0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4726    1.4210   -1.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787    1.8136    0.5215 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5462    0.5515    1.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2849   -0.1798    2.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3042   -0.8795    1.0781 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5854   -0.5261    0.6067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2182    0.4334    1.1650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1619   -1.2787   -0.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5112   -0.7865   -0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6457   -1.3192   -0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9204   -0.8830   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0858    0.1094   -1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9636    0.6663   -2.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7068    0.2127   -1.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5576   -1.0151    3.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2675   -2.2308    3.3160 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1279   -0.4923    4.4850 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6215   -0.2262    1.3641 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8036   -0.1424   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0730   -0.7819   -0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8081   -1.2979    0.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181   -0.8518   -1.7335 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8829    3.0952   -0.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7573    2.2801    1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8911    1.6643   -0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3215    2.4822   -2.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5155    0.8674   -2.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3164    1.0094   -2.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8531    1.1214    2.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4385    0.6121    2.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2077   -1.6594    0.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5143   -1.1699   -1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2627   -2.3410   -0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5555   -2.0996    0.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8100   -1.2982   -0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0841    0.4597   -1.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1244    1.4419   -2.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8490    0.6565   -2.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4998   -0.3071    5.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4972   -0.1991    1.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9988   -0.6640   -0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9907   -1.6822   -2.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
  5 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 21  2  1  0
 16 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 24 44  1  0
M  END


  Mrv0541 06151311042D          

 24 25  0  0  0  0            999 V2000
   -1.0934   -5.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7065   -5.2096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209   -4.7971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2494   -3.9902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0934   -4.6576    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0164   -1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -3.1895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2211   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914   -1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586   -1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836   -0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6961   -1.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836   -1.7605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1746   -5.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2609   -5.9532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8421   -4.6478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1914   -5.8771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 15 20  1  0  0  0  0
  3 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  2 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060617

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)SC(NC1C(O)=O)C(NC(=O)CC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O5S/c1-16(2)12(15(22)23)18-13(24-16)11(14(20)21)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-13,18H,8H2,1-2H3,(H,17,19)(H,20,21)(H,22,23)

> <INCHI_KEY>
HCYWNSXLUZRKJX-UHFFFAOYSA-N

> <FORMULA>
C16H20N2O5S

> <MOLECULAR_WEIGHT>
352.405

> <EXACT_MASS>
352.10929245

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
34.92844691970624

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[carboxy(2-phenylacetamido)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

> <ALOGPS_LOGP>
0.17

> <JCHEM_LOGP>
-1.217848462009146

> <ALOGPS_LOGS>
-3.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.5804124334346965

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.686780888299249

> <JCHEM_PKA_STRONGEST_BASIC>
6.637694328012496

> <JCHEM_POLAR_SURFACE_AREA>
115.73

> <JCHEM_REFRACTIVITY>
87.60560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.80e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[carboxy(2-phenylacetamido)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060617
     RDKit          3D
Penicilloic acid
 44 45  0  0  0  0  0  0  0  0999 V2000
    3.9018    2.1088    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7482    1.3046   -0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4726    1.4210   -1.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787    1.8136    0.5215 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5462    0.5515    1.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2849   -0.1798    2.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3042   -0.8795    1.0781 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5854   -0.5261    0.6067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2182    0.4334    1.1650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1619   -1.2787   -0.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5112   -0.7865   -0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6457   -1.3192   -0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9204   -0.8830   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0858    0.1094   -1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9636    0.6663   -2.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7068    0.2127   -1.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5576   -1.0151    3.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2675   -2.2308    3.3160 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1279   -0.4923    4.4850 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6215   -0.2262    1.3641 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8036   -0.1424   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0730   -0.7819   -0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8081   -1.2979    0.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181   -0.8518   -1.7335 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8829    3.0952   -0.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7573    2.2801    1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8911    1.6643   -0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3215    2.4822   -2.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5155    0.8674   -2.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3164    1.0094   -2.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8531    1.1214    2.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4385    0.6121    2.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2077   -1.6594    0.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5143   -1.1699   -1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2627   -2.3410   -0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5555   -2.0996    0.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8100   -1.2982   -0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0841    0.4597   -1.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1244    1.4419   -2.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8490    0.6565   -2.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4998   -0.3071    5.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4972   -0.1991    1.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9988   -0.6640   -0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9907   -1.6822   -2.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
  5 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 21  2  1  0
 16 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 24 44  1  0
M  END

HEADER    PROTEIN                                 15-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUN-13         0                                  
HETATM    1  C   UNK     0      -2.041 -10.755   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.185  -9.725   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.519  -8.955   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -4.199  -7.448   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -2.667  -7.287   0.000  0.00  0.00           C+0
HETATM    6  S   UNK     0      -2.041  -8.694   0.000  0.00  0.00           S+0
HETATM    7  C   UNK     0      -1.897  -5.954   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.207  -4.620   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.897  -3.286   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -0.357  -5.954   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       0.413  -4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.357  -3.286   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.953  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.723  -3.286   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.953  -1.953   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.723  -0.619   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.263  -0.619   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.033  -1.953   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.263  -3.286   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.926  -9.581   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -6.087 -11.113   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -7.172  -8.676   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.091 -10.971   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6   24                                             
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    2                                                       
CONECT    7    5    8   11                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    7   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   15                                                       
CONECT   21    3   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24    2                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0060617
HETATM    1  C1  UNL     1       3.902   2.109   0.021  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.748   1.305  -0.466  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.473   1.421  -1.923  1.00  0.00           C  
HETATM    4  S1  UNL     1       1.279   1.814   0.521  1.00  0.00           S  
HETATM    5  C4  UNL     1       1.546   0.552   1.825  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.285  -0.180   2.164  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.304  -0.880   1.078  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.585  -0.526   0.607  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.218   0.433   1.165  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.162  -1.279  -0.524  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.511  -0.787  -0.900  1.00  0.00           C  
HETATM   12  C9  UNL     1      -4.646  -1.319  -0.317  1.00  0.00           C  
HETATM   13  C10 UNL     1      -5.920  -0.883  -0.645  1.00  0.00           C  
HETATM   14  C11 UNL     1      -6.086   0.109  -1.576  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.964   0.666  -2.181  1.00  0.00           C  
HETATM   16  C13 UNL     1      -3.707   0.213  -1.836  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.558  -1.015   3.343  1.00  0.00           C  
HETATM   18  O2  UNL     1       0.268  -2.231   3.316  1.00  0.00           O  
HETATM   19  O3  UNL     1       1.128  -0.492   4.485  1.00  0.00           O  
HETATM   20  N2  UNL     1       2.621  -0.226   1.364  1.00  0.00           N  
HETATM   21  C15 UNL     1       2.804  -0.142  -0.027  1.00  0.00           C  
HETATM   22  C16 UNL     1       4.073  -0.782  -0.422  1.00  0.00           C  
HETATM   23  O4  UNL     1       4.808  -1.298   0.455  1.00  0.00           O  
HETATM   24  O5  UNL     1       4.518  -0.852  -1.733  1.00  0.00           O  
HETATM   25  H1  UNL     1       3.883   3.095  -0.485  1.00  0.00           H  
HETATM   26  H2  UNL     1       3.757   2.280   1.121  1.00  0.00           H  
HETATM   27  H3  UNL     1       4.891   1.664  -0.209  1.00  0.00           H  
HETATM   28  H4  UNL     1       2.321   2.482  -2.199  1.00  0.00           H  
HETATM   29  H5  UNL     1       1.516   0.867  -2.125  1.00  0.00           H  
HETATM   30  H6  UNL     1       3.316   1.009  -2.480  1.00  0.00           H  
HETATM   31  H7  UNL     1       1.853   1.121   2.728  1.00  0.00           H  
HETATM   32  H8  UNL     1      -0.438   0.612   2.502  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.208  -1.659   0.623  1.00  0.00           H  
HETATM   34  H10 UNL     1      -1.514  -1.170  -1.414  1.00  0.00           H  
HETATM   35  H11 UNL     1      -2.263  -2.341  -0.190  1.00  0.00           H  
HETATM   36  H12 UNL     1      -4.556  -2.100   0.417  1.00  0.00           H  
HETATM   37  H13 UNL     1      -6.810  -1.298  -0.191  1.00  0.00           H  
HETATM   38  H14 UNL     1      -7.084   0.460  -1.841  1.00  0.00           H  
HETATM   39  H15 UNL     1      -5.124   1.442  -2.907  1.00  0.00           H  
HETATM   40  H16 UNL     1      -2.849   0.656  -2.315  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.500  -0.307   5.263  1.00  0.00           H  
HETATM   42  H18 UNL     1       3.497  -0.199   1.897  1.00  0.00           H  
HETATM   43  H19 UNL     1       1.999  -0.664  -0.622  1.00  0.00           H  
HETATM   44  H20 UNL     1       4.991  -1.682  -2.100  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    4   21
CONECT    3   28   29   30
CONECT    4    5
CONECT    5    6   20   31
CONECT    6    7   17   32
CONECT    7    8   33
CONECT    8    9    9   10
CONECT   10   11   34   35
CONECT   11   12   12   16
CONECT   12   13   36
CONECT   13   14   14   37
CONECT   14   15   38
CONECT   15   16   16   39
CONECT   16   40
CONECT   17   18   18   19
CONECT   19   41
CONECT   20   21   42
CONECT   21   22   43
CONECT   22   23   23   24
CONECT   24   44
END

HMDB0060617
     RDKit          3D
Penicilloic acid
 44 45  0  0  0  0  0  0  0  0999 V2000
    3.9018    2.1088    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7482    1.3046   -0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4726    1.4210   -1.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2787    1.8136    0.5215 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5462    0.5515    1.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2849   -0.1798    2.1639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3042   -0.8795    1.0781 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5854   -0.5261    0.6067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2182    0.4334    1.1650 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1619   -1.2787   -0.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5112   -0.7865   -0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6457   -1.3192   -0.3175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9204   -0.8830   -0.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0858    0.1094   -1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9636    0.6663   -2.1812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7068    0.2127   -1.8356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5576   -1.0151    3.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2675   -2.2308    3.3160 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1279   -0.4923    4.4850 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6215   -0.2262    1.3641 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8036   -0.1424   -0.0266 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0730   -0.7819   -0.4222 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8081   -1.2979    0.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5181   -0.8518   -1.7335 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8829    3.0952   -0.4848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7573    2.2801    1.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8911    1.6643   -0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3215    2.4822   -2.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5155    0.8674   -2.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3164    1.0094   -2.4800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8531    1.1214    2.7281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4385    0.6121    2.5023 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2077   -1.6594    0.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5143   -1.1699   -1.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2627   -2.3410   -0.1901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5555   -2.0996    0.4174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8100   -1.2982   -0.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0841    0.4597   -1.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1244    1.4419   -2.9067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8490    0.6565   -2.3150 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4998   -0.3071    5.2627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4972   -0.1991    1.8967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9988   -0.6640   -0.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9907   -1.6822   -2.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
  5 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 21  2  1  0
 16 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  3 30  1  0
  5 31  1  0
  6 32  1  0
  7 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 16 40  1  0
 19 41  1  0
 20 42  1  0
 21 43  1  0
 24 44  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Penicilloate	Generator
Benzylpenicilloic acid, sodium salt, (2R-(2alpha(r*),4beta))-isomer	HMDB
Benzylpenicilloic acid, disodium salt, (2R-(2alpha(r*),4beta))-isomer	HMDB
Benzylpenicilloic acid, monosodium salt	HMDB
Benzylpenicilloic acid	HMDB
Penicilloic acid, disodium salt	HMDB
2-{carboxy[(1-hydroxy-2-phenylethylidene)amino]methyl}-5,5-dimethyl-1,3-thiazolidine-4-carboxylate	Generator

Chemical Formula

C₁₆H₂₀N₂O₅S

Average Molecular Weight

352.405

Monoisotopic Molecular Weight

352.10929245

IUPAC Name

2-[carboxy(2-phenylacetamido)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

Traditional Name

2-[carboxy(2-phenylacetamido)methyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(C)SC(NC1C(O)=O)C(NC(=O)CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C16H20N2O5S/c1-16(2)12(15(22)23)18-13(24-16)11(14(20)21)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-13,18H,8H2,1-2H3,(H,17,19)(H,20,21)(H,22,23)

InChI Key

HCYWNSXLUZRKJX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Phenylacetamide
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Benzenoid
Thiazolidine
Carboxamide group
Amino acid
Secondary carboxylic acid amide
Carboxylic acid
Secondary aliphatic amine
Secondary amine
Azacycle
Thioether
Hemithioaminal
Organoheterocyclic compound
Dialkylthioether
Organonitrogen compound
Organic oxide
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Amine
Organopnictogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060617)

Organ

Kidney (HMDB: HMDB0060617)
Liver (HMDB: HMDB0060617)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060617)

Cellular substructure

Cytoplasm (HMDB: HMDB0060617)

Source

Endogenous

Endogenous (HMDB: HMDB0060617)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.28 g/L	ALOGPS
logP	0.17	ALOGPS
logP	-1.2	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	2.69	ChemAxon
pKa (Strongest Basic)	6.64	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.73 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	87.61 m³·mol⁻¹	ChemAxon
Polarizability	34.93 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	183.809	31661259
DarkChem	[M-H]-	175.379	31661259
DeepCCS	[M+H]+	180.249	30932474
DeepCCS	[M-H]-	177.891	30932474
DeepCCS	[M-2H]-	210.777	30932474
DeepCCS	[M+Na]+	186.342	30932474
AllCCS	[M+H]+	179.4	32859911
AllCCS	[M+H-H2O]+	176.7	32859911
AllCCS	[M+NH4]+	181.9	32859911
AllCCS	[M+Na]+	182.7	32859911
AllCCS	[M-H]-	179.6	32859911
AllCCS	[M+Na-2H]-	179.8	32859911
AllCCS	[M+HCOO]-	180.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.51 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0153 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.36 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1315.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	201.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	97.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	160.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	55.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	298.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	319.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	463.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	676.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	381.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	934.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	203.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	237.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	335.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	322.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	161.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Penicilloic acid	CC1(C)SC(NC1C(O)=O)C(NC(=O)CC1=CC=CC=C1)C(O)=O	4175.4	Standard polar	33892256
Penicilloic acid	CC1(C)SC(NC1C(O)=O)C(NC(=O)CC1=CC=CC=C1)C(O)=O	2453.5	Standard non polar	33892256
Penicilloic acid	CC1(C)SC(NC1C(O)=O)C(NC(=O)CC1=CC=CC=C1)C(O)=O	2894.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Penicilloic acid,1TMS,isomer #1	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O)NC1C(=O)O[Si](C)(C)C	2883.6	Semi standard non polar	33892256
Penicilloic acid,1TMS,isomer #2	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O[Si](C)(C)C)NC1C(=O)O	2936.6	Semi standard non polar	33892256
Penicilloic acid,1TMS,isomer #3	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O)N([Si](C)(C)C)C1C(=O)O	2882.8	Semi standard non polar	33892256
Penicilloic acid,1TMS,isomer #4	CC1(C)SC(C(C(=O)O)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C)NC1C(=O)O	2940.7	Semi standard non polar	33892256
Penicilloic acid,2TMS,isomer #1	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O[Si](C)(C)C)NC1C(=O)O[Si](C)(C)C	2839.6	Semi standard non polar	33892256
Penicilloic acid,2TMS,isomer #2	CC1(C)SC(C(C(=O)O)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C)NC1C(=O)O[Si](C)(C)C	2800.6	Semi standard non polar	33892256
Penicilloic acid,2TMS,isomer #3	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O)N([Si](C)(C)C)C1C(=O)O[Si](C)(C)C	2816.8	Semi standard non polar	33892256
Penicilloic acid,2TMS,isomer #4	CC1(C)SC(C(C(=O)O[Si](C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C)NC1C(=O)O	2879.7	Semi standard non polar	33892256
Penicilloic acid,2TMS,isomer #5	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)C1C(=O)O	2840.3	Semi standard non polar	33892256
Penicilloic acid,2TMS,isomer #6	CC1(C)SC(C(C(=O)O)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C)N([Si](C)(C)C)C1C(=O)O	2847.6	Semi standard non polar	33892256
Penicilloic acid,3TMS,isomer #1	CC1(C)SC(C(C(=O)O[Si](C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C)NC1C(=O)O[Si](C)(C)C	2778.3	Semi standard non polar	33892256
Penicilloic acid,3TMS,isomer #1	CC1(C)SC(C(C(=O)O[Si](C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C)NC1C(=O)O[Si](C)(C)C	2720.6	Standard non polar	33892256
Penicilloic acid,3TMS,isomer #1	CC1(C)SC(C(C(=O)O[Si](C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C)NC1C(=O)O[Si](C)(C)C	3561.0	Standard polar	33892256
Penicilloic acid,3TMS,isomer #2	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)C1C(=O)O[Si](C)(C)C	2774.8	Semi standard non polar	33892256
Penicilloic acid,3TMS,isomer #2	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)C1C(=O)O[Si](C)(C)C	2664.0	Standard non polar	33892256
Penicilloic acid,3TMS,isomer #2	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O[Si](C)(C)C)N([Si](C)(C)C)C1C(=O)O[Si](C)(C)C	3297.0	Standard polar	33892256
Penicilloic acid,3TMS,isomer #3	CC1(C)SC(C(C(=O)O)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C)N([Si](C)(C)C)C1C(=O)O[Si](C)(C)C	2793.9	Semi standard non polar	33892256
Penicilloic acid,3TMS,isomer #3	CC1(C)SC(C(C(=O)O)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C)N([Si](C)(C)C)C1C(=O)O[Si](C)(C)C	2721.8	Standard non polar	33892256
Penicilloic acid,3TMS,isomer #3	CC1(C)SC(C(C(=O)O)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C)N([Si](C)(C)C)C1C(=O)O[Si](C)(C)C	3376.6	Standard polar	33892256
Penicilloic acid,3TMS,isomer #4	CC1(C)SC(C(C(=O)O[Si](C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C)N([Si](C)(C)C)C1C(=O)O	2821.9	Semi standard non polar	33892256
Penicilloic acid,3TMS,isomer #4	CC1(C)SC(C(C(=O)O[Si](C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C)N([Si](C)(C)C)C1C(=O)O	2699.8	Standard non polar	33892256
Penicilloic acid,3TMS,isomer #4	CC1(C)SC(C(C(=O)O[Si](C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C)N([Si](C)(C)C)C1C(=O)O	3421.9	Standard polar	33892256
Penicilloic acid,4TMS,isomer #1	CC1(C)SC(C(C(=O)O[Si](C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C)N([Si](C)(C)C)C1C(=O)O[Si](C)(C)C	2800.6	Semi standard non polar	33892256
Penicilloic acid,4TMS,isomer #1	CC1(C)SC(C(C(=O)O[Si](C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C)N([Si](C)(C)C)C1C(=O)O[Si](C)(C)C	2753.0	Standard non polar	33892256
Penicilloic acid,4TMS,isomer #1	CC1(C)SC(C(C(=O)O[Si](C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C)N([Si](C)(C)C)C1C(=O)O[Si](C)(C)C	3177.8	Standard polar	33892256
Penicilloic acid,1TBDMS,isomer #1	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O)NC1C(=O)O[Si](C)(C)C(C)(C)C	3142.4	Semi standard non polar	33892256
Penicilloic acid,1TBDMS,isomer #2	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O[Si](C)(C)C(C)(C)C)NC1C(=O)O	3201.8	Semi standard non polar	33892256
Penicilloic acid,1TBDMS,isomer #3	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O)N([Si](C)(C)C(C)(C)C)C1C(=O)O	3155.9	Semi standard non polar	33892256
Penicilloic acid,1TBDMS,isomer #4	CC1(C)SC(C(C(=O)O)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)NC1C(=O)O	3194.0	Semi standard non polar	33892256
Penicilloic acid,2TBDMS,isomer #1	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O[Si](C)(C)C(C)(C)C)NC1C(=O)O[Si](C)(C)C(C)(C)C	3288.5	Semi standard non polar	33892256
Penicilloic acid,2TBDMS,isomer #2	CC1(C)SC(C(C(=O)O)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)NC1C(=O)O[Si](C)(C)C(C)(C)C	3274.1	Semi standard non polar	33892256
Penicilloic acid,2TBDMS,isomer #3	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O)N([Si](C)(C)C(C)(C)C)C1C(=O)O[Si](C)(C)C(C)(C)C	3283.6	Semi standard non polar	33892256
Penicilloic acid,2TBDMS,isomer #4	CC1(C)SC(C(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)NC1C(=O)O	3346.7	Semi standard non polar	33892256
Penicilloic acid,2TBDMS,isomer #5	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1C(=O)O	3333.8	Semi standard non polar	33892256
Penicilloic acid,2TBDMS,isomer #6	CC1(C)SC(C(C(=O)O)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1C(=O)O	3351.0	Semi standard non polar	33892256
Penicilloic acid,3TBDMS,isomer #1	CC1(C)SC(C(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)NC1C(=O)O[Si](C)(C)C(C)(C)C	3405.0	Semi standard non polar	33892256
Penicilloic acid,3TBDMS,isomer #1	CC1(C)SC(C(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)NC1C(=O)O[Si](C)(C)C(C)(C)C	3284.0	Standard non polar	33892256
Penicilloic acid,3TBDMS,isomer #1	CC1(C)SC(C(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)NC1C(=O)O[Si](C)(C)C(C)(C)C	3783.4	Standard polar	33892256
Penicilloic acid,3TBDMS,isomer #2	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1C(=O)O[Si](C)(C)C(C)(C)C	3391.5	Semi standard non polar	33892256
Penicilloic acid,3TBDMS,isomer #2	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1C(=O)O[Si](C)(C)C(C)(C)C	3231.1	Standard non polar	33892256
Penicilloic acid,3TBDMS,isomer #2	CC1(C)SC(C(NC(=O)CC2=CC=CC=C2)C(=O)O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1C(=O)O[Si](C)(C)C(C)(C)C	3547.9	Standard polar	33892256
Penicilloic acid,3TBDMS,isomer #3	CC1(C)SC(C(C(=O)O)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1C(=O)O[Si](C)(C)C(C)(C)C	3459.0	Semi standard non polar	33892256
Penicilloic acid,3TBDMS,isomer #3	CC1(C)SC(C(C(=O)O)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1C(=O)O[Si](C)(C)C(C)(C)C	3276.3	Standard non polar	33892256
Penicilloic acid,3TBDMS,isomer #3	CC1(C)SC(C(C(=O)O)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1C(=O)O[Si](C)(C)C(C)(C)C	3606.1	Standard polar	33892256
Penicilloic acid,3TBDMS,isomer #4	CC1(C)SC(C(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1C(=O)O	3503.5	Semi standard non polar	33892256
Penicilloic acid,3TBDMS,isomer #4	CC1(C)SC(C(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1C(=O)O	3265.1	Standard non polar	33892256
Penicilloic acid,3TBDMS,isomer #4	CC1(C)SC(C(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1C(=O)O	3654.1	Standard polar	33892256
Penicilloic acid,4TBDMS,isomer #1	CC1(C)SC(C(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1C(=O)O[Si](C)(C)C(C)(C)C	3571.0	Semi standard non polar	33892256
Penicilloic acid,4TBDMS,isomer #1	CC1(C)SC(C(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1C(=O)O[Si](C)(C)C(C)(C)C	3458.7	Standard non polar	33892256
Penicilloic acid,4TBDMS,isomer #1	CC1(C)SC(C(C(=O)O[Si](C)(C)C(C)(C)C)N(C(=O)CC2=CC=CC=C2)[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)C1C(=O)O[Si](C)(C)C(C)(C)C	3494.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Penicilloic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-9312000000-434623c8ce300881debc	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Penicilloic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0006-9101200000-0c83da608573f9226cd7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Penicilloic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Penicilloic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicilloic acid 10V, Positive-QTOF	splash10-0hg9-1529000000-7258ee31dd9c1cbe8e01	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicilloic acid 20V, Positive-QTOF	splash10-014l-7963000000-b636594c20d9f5b4f688	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicilloic acid 40V, Positive-QTOF	splash10-03dl-9800000000-c89744bb28b5928a33b7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicilloic acid 10V, Negative-QTOF	splash10-01t9-0094000000-5daea6a8cd048d997892	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicilloic acid 20V, Negative-QTOF	splash10-07f0-2296000000-453468cc5815535203da	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicilloic acid 40V, Negative-QTOF	splash10-014i-9800000000-859731dfabdf627eebdb	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicilloic acid 10V, Positive-QTOF	splash10-0udi-0019000000-df61fc2a46ad20edf91c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicilloic acid 20V, Positive-QTOF	splash10-0gvo-3915000000-9c4c0431a44152aff62b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicilloic acid 40V, Positive-QTOF	splash10-0006-8900000000-664c4b4c66822308e324	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicilloic acid 10V, Negative-QTOF	splash10-114i-0169000000-d3f36b197a5ce1c907fa	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicilloic acid 20V, Negative-QTOF	splash10-0079-8922000000-613c6d93d3e5ccec6bcf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Penicilloic acid 40V, Negative-QTOF	splash10-0006-9700000000-88a694b4fbcebbdf931e	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Penicilloic acid

METLIN ID

Not Available

PubChem Compound

98994

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Penicilloic acid (HMDB0060617)

MOL for HMDB0060617 (Penicilloic acid)

3D MOL for HMDB0060617 (Penicilloic acid)

3D SDF for HMDB0060617 (Penicilloic acid)

3D-SDF for HMDB0060617 (Penicilloic acid)

PDB for HMDB0060617 (Penicilloic acid)

3D PDB for HMDB0060617 (Penicilloic acid)

SMILES for HMDB0060617 (Penicilloic acid)

INCHI for HMDB0060617 (Penicilloic acid)

Structure for HMDB0060617 (Penicilloic acid)

3D Structure for HMDB0060617 (Penicilloic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra