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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:52 UTC

HMDB ID

HMDB0015135

Secondary Accession Numbers

HMDB15135

Metabolite Identification

Common Name

Cyclacillin

Description

Cyclacillin, also known as cyclapen-W or vastcillin, belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1]. A large randomized, double-blind clinical trial published in 1978 also showed that ciclacillin is associated with significantly fewer and milder adverse effects than ampicillin; later studies seemed to confirm this improved tolerability, at least in children. Ciclacillin has been superseded by newer antibiotics and is no longer in clinical use, at least in the United States. Cyclacillin is a drug which is used for the treatment of bacterial infections caused by susceptible organisms. Its spectrum of activity is similar to that of ampicillin, although it is less susceptible to beta-lactamases than ampicillin and has much higher bioavailability. Reaction of cyclohexanone with ammonium carbonate and KCN under the conditions of the Bucherer-Bergs reaction led to hydantoin 1. Treatment with phosgene both protected the amino group and activated the carboxyl group toward amide formation (as 3) and reaction with 6-aminopenicillanic acid (6-APA) gave cyclacillin (4). Cyclacillin is a very strong basic compound (based on its pKa). On acid hydrolysis, α-amino acid 2 resulted. This artifice seems to have worked, since cyclacillin is more active in vivo than its in vitro spectrum suggests. Ciclacillin (INN) or cyclacillin (USAN), trade names Cyclapen, Cyclapen-W, Vastcillin, and others, is an aminopenicillin antibiotic.

Structure

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

HMDB0015135
     RDKit          3D
Cyclacillin
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.7033    0.0993    0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4371   -0.6942    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6282   -2.1233    0.7381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3453    0.1786    1.5689 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1531    1.5491    0.4063 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8174    2.0521    0.0666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3077    1.1934    0.2067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5483    1.6163    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6378    2.8091    1.1253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7186    0.7364    0.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8119    1.4789    1.4905 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4274   -0.4297    1.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8125   -1.7414    1.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2992   -1.6594    0.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4903   -0.5694   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2080    0.1926   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3931    1.9680   -1.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289    2.6160   -2.3674 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0509    0.8053   -0.8691 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6096   -0.4804   -0.8589 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3665   -0.7202   -2.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9376   -1.8122   -2.2734 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4438    0.2566   -3.0606 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5445    0.9312   -0.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5816   -0.4659   -0.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8737    0.5962    1.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2813   -2.8487   -0.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1822   -2.2927    1.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7346   -2.2915    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9259    2.3145    0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6782    3.1037    0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2506    0.1981   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613    2.5070    1.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6882    1.4172    2.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0109   -0.3718    2.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3597   -0.4677    2.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2104   -1.9758    0.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6609   -2.5471    1.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7110   -2.6019    0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8085   -1.3351    1.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2426    0.1811    0.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8476   -0.9919   -1.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5256    1.0575   -1.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4622   -0.3867   -0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8331   -1.3108   -0.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9510    0.2595   -3.9371 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
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20  2  1  0
 19  5  1  0
 16 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  6
  6 31  1  1
  7 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 20 45  1  1
 23 46  1  0
M  END

1000
  Mrv0541 02231215102D          

 24 26  0  0  1  0            999 V2000
    6.2365    0.4594    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0378   -1.2085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9394   -2.2733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3108   -0.2415    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2984   -1.8317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4519   -0.6206    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0378    0.7924    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1838    0.4902    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4519    0.2044    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6200    0.2078    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2365   -0.8755    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7214   -0.2081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6200   -0.6240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6583    1.1651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3888   -0.6930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3888    0.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2429    1.7472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8619    1.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2405    0.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4914   -1.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0311    2.5446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2346    2.7597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3499    0.8565    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 12  1  0  0  0  0
  2 13  2  0  0  0  0
  3 20  1  0  0  0  0
  4 19  2  0  0  0  0
  5 20  2  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  6 13  1  0  0  0  0
 10  7  1  1  0  0  0
  7 19  1  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
  9 24  1  6  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 20  1  6  0  0  0
 12 15  1  0  0  0  0
 12 16  1  0  0  0  0
 14 17  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  1  0  0  0  0
 17 21  1  0  0  0  0
 18 22  1  0  0  0  0
 21 23  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015135

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1(N)CCCCC1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H23N3O4S/c1-14(2)9(12(20)21)18-10(19)8(11(18)23-14)17-13(22)15(16)6-4-3-5-7-15/h8-9,11H,3-7,16H2,1-2H3,(H,17,22)(H,20,21)/t8-,9+,11-/m1/s1

> <INCHI_KEY>
HGBLNBBNRORJKI-WCABBAIRSA-N

> <FORMULA>
C15H23N3O4S

> <MOLECULAR_WEIGHT>
341.426

> <EXACT_MASS>
341.140926929

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
34.813095816532574

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,5R,6R)-6-(1-aminocyclohexaneamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

> <ALOGPS_LOGP>
0.56

> <JCHEM_LOGP>
-1.9145717180744428

> <ALOGPS_LOGS>
-2.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.077202392830863

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.304205732178046

> <JCHEM_PKA_STRONGEST_BASIC>
8.450183681449174

> <JCHEM_POLAR_SURFACE_AREA>
112.72999999999999

> <JCHEM_REFRACTIVITY>
84.2196

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cyclacillin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015135
     RDKit          3D
Cyclacillin
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.7033    0.0993    0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4371   -0.6942    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6282   -2.1233    0.7381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3453    0.1786    1.5689 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1531    1.5491    0.4063 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8174    2.0521    0.0666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3077    1.1934    0.2067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5483    1.6163    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6378    2.8091    1.1253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7186    0.7364    0.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8119    1.4789    1.4905 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4274   -0.4297    1.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8125   -1.7414    1.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2992   -1.6594    0.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4903   -0.5694   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2080    0.1926   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3931    1.9680   -1.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289    2.6160   -2.3674 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0509    0.8053   -0.8691 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6096   -0.4804   -0.8589 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3665   -0.7202   -2.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9376   -1.8122   -2.2734 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4438    0.2566   -3.0606 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5445    0.9312   -0.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5816   -0.4659   -0.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8737    0.5962    1.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2813   -2.8487   -0.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1822   -2.2927    1.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7346   -2.2915    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9259    2.3145    0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6782    3.1037    0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2506    0.1981   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613    2.5070    1.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6882    1.4172    2.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0109   -0.3718    2.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3597   -0.4677    2.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2104   -1.9758    0.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6609   -2.5471    1.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7110   -2.6019    0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8085   -1.3351    1.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2426    0.1811    0.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8476   -0.9919   -1.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5256    1.0575   -1.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4622   -0.3867   -0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8331   -1.3108   -0.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9510    0.2595   -3.9371 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
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20  2  1  0
 19  5  1  0
 16 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  6
  6 31  1  1
  7 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 20 45  1  1
 23 46  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1000                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      11.641   0.858   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       7.537  -2.256   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      11.087  -4.243   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.180  -0.451   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      13.624  -3.419   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      10.177  -1.158   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       7.537   1.479   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       4.076   0.915   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      10.177   0.382   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.624   0.388   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.641  -1.634   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.547  -0.388   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.624  -1.165   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.962   2.175   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.792  -1.294   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.792   0.517   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.053   3.261   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.476   2.576   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.049   1.084   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.117  -3.099   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.658   4.750   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.080   4.065   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.171   5.151   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       9.986   1.599   0.000  0.00  0.00           H+0
CONECT    1    9   12                                                       
CONECT    2   13                                                            
CONECT    3   20                                                            
CONECT    4   19                                                            
CONECT    5   20                                                            
CONECT    6    9   11   13                                                  
CONECT    7   10   19                                                       
CONECT    8   14                                                            
CONECT    9    1    6   10   24                                             
CONECT   10    7    9   13                                                  
CONECT   11    6   12   20                                                  
CONECT   12    1   11   15   16                                             
CONECT   13    2    6   10                                                  
CONECT   14    8   17   18   19                                             
CONECT   15   12                                                            
CONECT   16   12                                                            
CONECT   17   14   21                                                       
CONECT   18   14   22                                                       
CONECT   19    4    7   14                                                  
CONECT   20    3    5   11                                                  
CONECT   21   17   23                                                       
CONECT   22   18   23                                                       
CONECT   23   21   22                                                       
CONECT   24    9                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0015135
HETATM    1  C1  UNL     1       4.703   0.099   0.294  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.437  -0.694   0.359  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.628  -2.123   0.738  1.00  0.00           C  
HETATM    4  S1  UNL     1       2.345   0.179   1.569  1.00  0.00           S  
HETATM    5  C4  UNL     1       2.153   1.549   0.406  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.817   2.052   0.067  1.00  0.00           C  
HETATM    7  N1  UNL     1      -0.308   1.193   0.207  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.548   1.616   0.753  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.638   2.809   1.125  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.719   0.736   0.903  1.00  0.00           C  
HETATM   11  N2  UNL     1      -3.812   1.479   1.491  1.00  0.00           N  
HETATM   12  C8  UNL     1      -2.427  -0.430   1.825  1.00  0.00           C  
HETATM   13  C9  UNL     1      -2.813  -1.741   1.171  1.00  0.00           C  
HETATM   14  C10 UNL     1      -4.299  -1.659   0.872  1.00  0.00           C  
HETATM   15  C11 UNL     1      -4.490  -0.569  -0.144  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.208   0.193  -0.420  1.00  0.00           C  
HETATM   17  C13 UNL     1       1.393   1.968  -1.312  1.00  0.00           C  
HETATM   18  O2  UNL     1       1.329   2.616  -2.367  1.00  0.00           O  
HETATM   19  N3  UNL     1       2.051   0.805  -0.869  1.00  0.00           N  
HETATM   20  C14 UNL     1       2.610  -0.480  -0.859  1.00  0.00           C  
HETATM   21  C15 UNL     1       3.366  -0.720  -2.098  1.00  0.00           C  
HETATM   22  O3  UNL     1       3.938  -1.812  -2.273  1.00  0.00           O  
HETATM   23  O4  UNL     1       3.444   0.257  -3.061  1.00  0.00           O  
HETATM   24  H1  UNL     1       4.544   0.931  -0.423  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.582  -0.466  -0.050  1.00  0.00           H  
HETATM   26  H3  UNL     1       4.874   0.596   1.287  1.00  0.00           H  
HETATM   27  H4  UNL     1       3.281  -2.849  -0.003  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.182  -2.293   1.737  1.00  0.00           H  
HETATM   29  H6  UNL     1       4.735  -2.291   0.868  1.00  0.00           H  
HETATM   30  H7  UNL     1       2.926   2.315   0.415  1.00  0.00           H  
HETATM   31  H8  UNL     1       0.678   3.104   0.415  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.251   0.198  -0.098  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.761   2.507   1.274  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.688   1.417   2.540  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.011  -0.372   2.774  1.00  0.00           H  
HETATM   36  H13 UNL     1      -1.360  -0.468   2.134  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.210  -1.976   0.292  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.661  -2.547   1.913  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.711  -2.602   0.485  1.00  0.00           H  
HETATM   40  H17 UNL     1      -4.808  -1.335   1.804  1.00  0.00           H  
HETATM   41  H18 UNL     1      -5.243   0.181   0.158  1.00  0.00           H  
HETATM   42  H19 UNL     1      -4.848  -0.992  -1.111  1.00  0.00           H  
HETATM   43  H20 UNL     1      -3.526   1.057  -1.074  1.00  0.00           H  
HETATM   44  H21 UNL     1      -2.462  -0.387  -0.963  1.00  0.00           H  
HETATM   45  H22 UNL     1       1.833  -1.311  -0.834  1.00  0.00           H  
HETATM   46  H23 UNL     1       2.951   0.260  -3.937  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4   20
CONECT    3   27   28   29
CONECT    4    5
CONECT    5    6   19   30
CONECT    6    7   17   31
CONECT    7    8   32
CONECT    8    9    9   10
CONECT   10   11   12   16
CONECT   11   33   34
CONECT   12   13   35   36
CONECT   13   14   37   38
CONECT   14   15   39   40
CONECT   15   16   41   42
CONECT   16   43   44
CONECT   17   18   18   19
CONECT   19   20
CONECT   20   21   45
CONECT   21   22   22   23
CONECT   23   46
END

HMDB0015135
     RDKit          3D
Cyclacillin
 46 48  0  0  0  0  0  0  0  0999 V2000
    4.7033    0.0993    0.2937 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4371   -0.6942    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6282   -2.1233    0.7381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3453    0.1786    1.5689 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1531    1.5491    0.4063 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8174    2.0521    0.0666 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3077    1.1934    0.2067 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5483    1.6163    0.7533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6378    2.8091    1.1253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7186    0.7364    0.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8119    1.4789    1.4905 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4274   -0.4297    1.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8125   -1.7414    1.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2992   -1.6594    0.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4903   -0.5694   -0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2080    0.1926   -0.4202 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3931    1.9680   -1.3125 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3289    2.6160   -2.3674 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0509    0.8053   -0.8691 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6096   -0.4804   -0.8589 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3665   -0.7202   -2.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9376   -1.8122   -2.2734 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4438    0.2566   -3.0606 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5445    0.9312   -0.4231 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5816   -0.4659   -0.0502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8737    0.5962    1.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2813   -2.8487   -0.0035 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1822   -2.2927    1.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7346   -2.2915    0.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9259    2.3145    0.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6782    3.1037    0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2506    0.1981   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7613    2.5070    1.2742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6882    1.4172    2.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0109   -0.3718    2.7742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3597   -0.4677    2.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2104   -1.9758    0.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6609   -2.5471    1.9127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7110   -2.6019    0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8085   -1.3351    1.8039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2426    0.1811    0.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8476   -0.9919   -1.1109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5256    1.0575   -1.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4622   -0.3867   -0.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8331   -1.3108   -0.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9510    0.2595   -3.9371 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
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  6 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20  2  1  0
 19  5  1  0
 16 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  6
  6 31  1  1
  7 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 20 45  1  1
 23 46  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(1-Aminocyclohexyl)penicillin	ChEBI
(2S,5R,6R)-6-{[(1-aminocyclohexyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
6-(1-Aminocyclohexanecarboxamido)penicillanic acid	ChEBI
6-(1-Aminocyclohexylcarboxamido)penicillanic acid	ChEBI
Bastcillin	ChEBI
Calthor	ChEBI
Ciclacilina	ChEBI
Ciclacillin	ChEBI
Ciclacilline	ChEBI
Ciclacillinum	ChEBI
Citosarin	ChEBI
Cyclapen	ChEBI
Cyclapen-W	ChEBI
Syngacillin	ChEBI
Ultracillin	ChEBI
Vastcillin	ChEBI
Vipicil	ChEBI
Wyvital	ChEBI
ACPC	Kegg
(2S,5R,6R)-6-{[(1-aminocyclohexyl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
6-(1-Aminocyclohexanecarboxamido)penicillanate	Generator
6-(1-Aminocyclohexylcarboxamido)penicillanate	Generator
Aminocyclohexylpenicillin	HMDB
Ciclacillum	HMDB

Chemical Formula

C₁₅H₂₃N₃O₄S

Average Molecular Weight

341.426

Monoisotopic Molecular Weight

341.140926929

IUPAC Name

(2S,5R,6R)-6-(1-aminocyclohexaneamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

cyclacillin

CAS Registry Number

3485-14-1

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1(N)CCCCC1)C(O)=O

InChI Identifier

InChI=1S/C15H23N3O4S/c1-14(2)9(12(20)21)18-10(19)8(11(18)23-14)17-13(22)15(16)6-4-3-5-7-15/h8-9,11H,3-7,16H2,1-2H3,(H,17,22)(H,20,21)/t8-,9+,11-/m1/s1

InChI Key

HGBLNBBNRORJKI-WCABBAIRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Penicillins

Alternative Parents

Substituents

Penicillin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Alpha-amino acid or derivatives
Cyclohexylamine
Thiazolidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Azetidine
Amino acid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Dialkylthioether
Hemithioaminal
Thioether
Primary aliphatic amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Primary amine
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:31444 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015135)
Membrane (HMDB: HMDB0015135)

Source

Exogenous

Exogenous (HMDB: HMDB0015135)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.9 g/L	Not Available
LogP	0.4	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.9 g/L	ALOGPS
logP	0.56	ALOGPS
logP	-1.9	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	8.45	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	112.73 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.22 m³·mol⁻¹	ChemAxon
Polarizability	34.81 Å³	ChemAxon
Number of Rings	3	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]+	177.158	31661259
DarkChem	[M-H]-	168.59	31661259
DeepCCS	[M-2H]-	218.528	30932474
DeepCCS	[M+Na]+	193.692	30932474
AllCCS	[M+H]+	176.1	32859911
AllCCS	[M+H-H2O]+	173.5	32859911
AllCCS	[M+NH4]+	178.5	32859911
AllCCS	[M+Na]+	179.1	32859911
AllCCS	[M-H]-	178.0	32859911
AllCCS	[M+Na-2H]-	178.1	32859911
AllCCS	[M+HCOO]-	178.3	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.	3.06 minutes	32390414
Predicted by Siyang on May 30, 2022	10.9342 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.27 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1797.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	192.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	124.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	154.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	94.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	317.3 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	355.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	360.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	807.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	351.6 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	1088.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	228.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	262.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	330.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	310.5 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	147.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyclacillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1(N)CCCCC1)C(O)=O	3646.8	Standard polar	33892256
Cyclacillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1(N)CCCCC1)C(O)=O	2653.8	Standard non polar	33892256
Cyclacillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1(N)CCCCC1)C(O)=O	2820.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cyclacillin,1TMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2641.2	Semi standard non polar	33892256
Cyclacillin,1TMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O	2733.2	Semi standard non polar	33892256
Cyclacillin,1TMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	2605.1	Semi standard non polar	33892256
Cyclacillin,2TMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2693.7	Semi standard non polar	33892256
Cyclacillin,2TMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2724.0	Standard non polar	33892256
Cyclacillin,2TMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3883.2	Standard polar	33892256
Cyclacillin,2TMS,isomer #2	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2598.4	Semi standard non polar	33892256
Cyclacillin,2TMS,isomer #2	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2641.0	Standard non polar	33892256
Cyclacillin,2TMS,isomer #2	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	4057.4	Standard polar	33892256
Cyclacillin,2TMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	2665.7	Semi standard non polar	33892256
Cyclacillin,2TMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	2725.2	Standard non polar	33892256
Cyclacillin,2TMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	3713.9	Standard polar	33892256
Cyclacillin,2TMS,isomer #4	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O	2763.5	Semi standard non polar	33892256
Cyclacillin,2TMS,isomer #4	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O	2790.1	Standard non polar	33892256
Cyclacillin,2TMS,isomer #4	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O	3997.9	Standard polar	33892256
Cyclacillin,3TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2682.1	Semi standard non polar	33892256
Cyclacillin,3TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2796.5	Standard non polar	33892256
Cyclacillin,3TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3405.3	Standard polar	33892256
Cyclacillin,3TMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2746.1	Semi standard non polar	33892256
Cyclacillin,3TMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2863.9	Standard non polar	33892256
Cyclacillin,3TMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3717.3	Standard polar	33892256
Cyclacillin,3TMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	2764.0	Semi standard non polar	33892256
Cyclacillin,3TMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	2883.3	Standard non polar	33892256
Cyclacillin,3TMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O	3584.4	Standard polar	33892256
Cyclacillin,4TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2778.2	Semi standard non polar	33892256
Cyclacillin,4TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2919.7	Standard non polar	33892256
Cyclacillin,4TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C)[Si](C)(C)C)CCCCC3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3257.5	Standard polar	33892256
Cyclacillin,1TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	2882.6	Semi standard non polar	33892256
Cyclacillin,1TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O	2943.7	Semi standard non polar	33892256
Cyclacillin,1TBDMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	2832.0	Semi standard non polar	33892256
Cyclacillin,2TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3120.9	Semi standard non polar	33892256
Cyclacillin,2TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3143.2	Standard non polar	33892256
Cyclacillin,2TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3910.1	Standard polar	33892256
Cyclacillin,2TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3035.3	Semi standard non polar	33892256
Cyclacillin,2TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3067.0	Standard non polar	33892256
Cyclacillin,2TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	4099.8	Standard polar	33892256
Cyclacillin,2TBDMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3096.1	Semi standard non polar	33892256
Cyclacillin,2TBDMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3133.6	Standard non polar	33892256
Cyclacillin,2TBDMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3771.7	Standard polar	33892256
Cyclacillin,2TBDMS,isomer #4	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O	3227.8	Semi standard non polar	33892256
Cyclacillin,2TBDMS,isomer #4	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O	3200.0	Standard non polar	33892256
Cyclacillin,2TBDMS,isomer #4	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O	3987.5	Standard polar	33892256
Cyclacillin,3TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3282.0	Semi standard non polar	33892256
Cyclacillin,3TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3379.0	Standard non polar	33892256
Cyclacillin,3TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3591.9	Standard polar	33892256
Cyclacillin,3TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3383.1	Semi standard non polar	33892256
Cyclacillin,3TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3433.6	Standard non polar	33892256
Cyclacillin,3TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](NC(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3778.7	Standard polar	33892256
Cyclacillin,3TBDMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3406.4	Semi standard non polar	33892256
Cyclacillin,3TBDMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3448.7	Standard non polar	33892256
Cyclacillin,3TBDMS,isomer #3	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O	3711.3	Standard polar	33892256
Cyclacillin,4TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3583.0	Semi standard non polar	33892256
Cyclacillin,4TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3635.2	Standard non polar	33892256
Cyclacillin,4TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](N(C(=O)C3(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)CCCCC3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3497.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclacillin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9110000000-880dc522fc28c1bba7cb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclacillin GC-MS (1 TMS) - 70eV, Positive	splash10-0002-9000000000-68fd157b54c0f0c04c1a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclacillin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyclacillin 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 - Cyclacillin 10V, Positive-QTOF	splash10-03ea-3913000000-e1b225a6069c25031e80	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclacillin 20V, Positive-QTOF	splash10-01pk-6900000000-9015a0229a34616fbc41	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclacillin 40V, Positive-QTOF	splash10-05u5-9100000000-ebbfbef8f7baae6dadba	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclacillin 10V, Negative-QTOF	splash10-0002-0911000000-0b9e6a3d9d3b19d46cac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclacillin 20V, Negative-QTOF	splash10-0002-0930000000-738172cee45fa138ecea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclacillin 40V, Negative-QTOF	splash10-002b-9400000000-e5e5efd7b191cd291cea	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclacillin 10V, Positive-QTOF	splash10-0006-0009000000-f94d572cb27dd62c4495	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclacillin 20V, Positive-QTOF	splash10-004l-4529000000-90a2bebebc953a6db79c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclacillin 40V, Positive-QTOF	splash10-0a59-7922000000-40fa844297d16d9e505b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclacillin 10V, Negative-QTOF	splash10-0006-0019000000-02832c883fa4bd6dfa39	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclacillin 20V, Negative-QTOF	splash10-0007-9834000000-12493a6db58de235a70b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyclacillin 40V, Negative-QTOF	splash10-00di-8901000000-5c2d54fc89ea21fd80a1	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

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	Taking drug identified by DrugBank entry DB01000	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01000	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01000

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

17941

KEGG Compound ID

C12766

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ciclacillin

METLIN ID

Not Available

PubChem Compound

19003

PDB ID

Not Available

ChEBI ID

31444

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

Transporters

Enzyme Details

1. Solute carrier family 22 member 5

General function:: Involved in ion transmembrane transporter activity
Specific function:: Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also relative uptake activity ratio of carnitine to TEA is 11.3
Gene Name:: SLC22A5
Uniprot ID:: O76082
Molecular weight:: 62751.1

References

Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865 ]

Enzyme Details

2. Solute carrier family 15 member 1

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products
Gene Name:: SLC15A1
Uniprot ID:: P46059
Molecular weight:: 78805.3

References

Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. [PubMed:7592745 ]
Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]
Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]

Enzyme Details

3. Solute carrier family 15 member 2

General function:: Involved in transporter activity
Specific function:: Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides
Gene Name:: SLC15A2
Uniprot ID:: Q16348
Molecular weight:: 81782.8

References

Ganapathy ME, Brandsch M, Prasad PD, Ganapathy V, Leibach FH: Differential recognition of beta -lactam antibiotics by intestinal and renal peptide transporters, PEPT 1 and PEPT 2. J Biol Chem. 1995 Oct 27;270(43):25672-7. [PubMed:7592745 ]
Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833 ]
Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]

Showing metabocard for Cyclacillin (HMDB0015135)

MOL for HMDB0015135 (Cyclacillin)

3D MOL for HMDB0015135 (Cyclacillin)

3D SDF for HMDB0015135 (Cyclacillin)

3D-SDF for HMDB0015135 (Cyclacillin)

PDB for HMDB0015135 (Cyclacillin)

3D PDB for HMDB0015135 (Cyclacillin)

SMILES for HMDB0015135 (Cyclacillin)

INCHI for HMDB0015135 (Cyclacillin)

Structure for HMDB0015135 (Cyclacillin)

3D Structure for HMDB0015135 (Cyclacillin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Transporters

References

References

References