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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:46 UTC

HMDB ID

HMDB0014877

Secondary Accession Numbers

HMDB14877

Metabolite Identification

Common Name

Hetacillin

Description

Hetacillin is a penicillin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. The name 'penicillin' can either refer to several variants of penicillin available, or to the group of antibiotics derived from the penicillins. Hetacillin has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Hetacillin results from the inhibition of cell wall synthesis and is mediated through Hetacillin binding to penicillin binding proteins (PBPs).

Structure

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

739
  Mrv0541 02231214582D          

 28 31  0  0  1  0            999 V2000
    7.4805    0.5950    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2819   -1.0729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0907    0.0663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1834   -2.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5424   -1.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6959   -0.4849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2819    0.9280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6784    2.1187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6959    0.3401    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8640    0.3435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4805   -0.7399    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9654   -0.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8640   -0.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4126    1.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4668    0.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0938    1.5365    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6329   -0.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6329    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7355   -1.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2272    1.6119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7886    2.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2791    1.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7586    1.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9851    2.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9440    1.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1705    2.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5940    0.9922    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 15  2  0  0  0  0
  4 19  1  0  0  0  0
  5 19  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 14  1  0  0  0  0
  7 15  1  0  0  0  0
  8 14  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  1  0  0  0  0
  9 28  1  6  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 19  1  6  0  0  0
 12 17  1  0  0  0  0
 12 18  1  0  0  0  0
 14 20  1  0  0  0  0
 14 21  1  0  0  0  0
 15 16  1  0  0  0  0
 16 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  2  0  0  0  0
 25 27  2  0  0  0  0
 26 27  1  0  0  0  0
M  END

HMDB0014877
     RDKit          3D
Hetacillin
 50 53  0  0  0  0  0  0  0  0999 V2000
   -3.6365    0.5196   -2.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7077    0.2382   -0.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1415    0.3040   -0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    1.4433    0.0813 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2360    0.3001    1.3428 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8761    0.0058    1.7726 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3074    0.3044    1.1095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4363    1.0402    1.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6109    1.1062    2.9668 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2546    1.6410    0.6942 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6803    1.2409    0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2706    0.6141    1.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6239    0.2646    1.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3427    0.5549    0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7541    1.1809   -0.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4336    1.5253   -0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5936    1.2436   -0.5415 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701    0.0191   -0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0481   -0.4126   -1.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493   -1.0734    0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3144   -1.3828    1.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -2.5082    2.1281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538   -0.9743    0.6719 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1153   -1.0460   -0.4344 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1910   -2.0579   -0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2173   -2.6554    1.0172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1794   -2.3246   -1.0064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473   -0.0874   -2.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6473    0.2974   -2.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3800    1.5829   -2.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4241    1.3343   -0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8186   -0.0800   -1.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2021   -0.3314    0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9451    0.2293    2.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884    0.3012    2.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1862    2.7765    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7259    0.3784    2.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0400   -0.2195    2.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3773    0.2759    0.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3316    1.4046   -1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9668    2.0270   -1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2521    0.9381   -1.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208   -0.4906   -2.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7617    0.2326   -1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2672   -1.4825   -1.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8615   -0.8927   -0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4699   -2.0215   -0.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0957   -1.1961    1.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6363   -1.4689   -1.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9011   -2.6185   -1.9297 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
 10 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
  6 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 24  2  1  0
 23  5  1  0
 18  7  1  0
 16 11  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  3 33  1  0
  5 34  1  1
  6 35  1  1
 10 36  1  1
 12 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 24 49  1  6
 27 50  1  0
M  END

739
  Mrv0541 02231214582D          

 28 31  0  0  1  0            999 V2000
    7.4805    0.5950    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2819   -1.0729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0907    0.0663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1834   -2.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5424   -1.6960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6959   -0.4849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2819    0.9280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6784    2.1187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6959    0.3401    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8640    0.3435    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.4805   -0.7399    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.9654   -0.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8640   -0.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4126    1.7427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4668    0.8007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0938    1.5365    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.6329   -0.5574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6329    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7355   -1.5245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2272    1.6119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7886    2.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2791    1.6673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7586    1.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9851    2.4381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9440    1.1579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1705    2.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5940    0.9922    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 15  2  0  0  0  0
  4 19  1  0  0  0  0
  5 19  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 14  1  0  0  0  0
  7 15  1  0  0  0  0
  8 14  1  0  0  0  0
  8 16  1  0  0  0  0
  9 10  1  0  0  0  0
  9 28  1  6  0  0  0
 10 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 19  1  6  0  0  0
 12 17  1  0  0  0  0
 12 18  1  0  0  0  0
 14 20  1  0  0  0  0
 14 21  1  0  0  0  0
 15 16  1  0  0  0  0
 16 22  1  1  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 23 25  1  0  0  0  0
 24 26  2  0  0  0  0
 25 27  2  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014877

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2N1C(=O)[C@H](NC1(C)C)C1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11-,12-,13+,16-/m1/s1

> <INCHI_KEY>
DXVUYOAEDJXBPY-NFFDBFGFSA-N

> <FORMULA>
C19H23N3O4S

> <MOLECULAR_WEIGHT>
389.469

> <EXACT_MASS>
389.140926929

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.58154278946702

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.85

> <JCHEM_LOGP>
-0.015010228405816369

> <ALOGPS_LOGS>
-2.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.993524451963172

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.626005434143019

> <JCHEM_PKA_STRONGEST_BASIC>
5.474500567056694

> <JCHEM_POLAR_SURFACE_AREA>
89.94999999999999

> <JCHEM_REFRACTIVITY>
99.89940000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.12e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hetacillin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014877
     RDKit          3D
Hetacillin
 50 53  0  0  0  0  0  0  0  0999 V2000
   -3.6365    0.5196   -2.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7077    0.2382   -0.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1415    0.3040   -0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    1.4433    0.0813 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2360    0.3001    1.3428 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8761    0.0058    1.7726 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3074    0.3044    1.1095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4363    1.0402    1.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6109    1.1062    2.9668 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2546    1.6410    0.6942 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6803    1.2409    0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2706    0.6141    1.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6239    0.2646    1.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3427    0.5549    0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7541    1.1809   -0.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4336    1.5253   -0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5936    1.2436   -0.5415 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701    0.0191   -0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0481   -0.4126   -1.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493   -1.0734    0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3144   -1.3828    1.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -2.5082    2.1281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538   -0.9743    0.6719 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1153   -1.0460   -0.4344 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1910   -2.0579   -0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2173   -2.6554    1.0172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1794   -2.3246   -1.0064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473   -0.0874   -2.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6473    0.2974   -2.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3800    1.5829   -2.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4241    1.3343   -0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8186   -0.0800   -1.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2021   -0.3314    0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9451    0.2293    2.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884    0.3012    2.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1862    2.7765    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7259    0.3784    2.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0400   -0.2195    2.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3773    0.2759    0.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3316    1.4046   -1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9668    2.0270   -1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2521    0.9381   -1.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208   -0.4906   -2.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7617    0.2326   -1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2672   -1.4825   -1.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8615   -0.8927   -0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4699   -2.0215   -0.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0957   -1.1961    1.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6363   -1.4689   -1.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9011   -2.6185   -1.9297 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
 10 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
  6 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 24  2  1  0
 23  5  1  0
 18  7  1  0
 16 11  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  3 33  1  0
  5 34  1  1
  6 35  1  1
 10 36  1  1
 12 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 24 49  1  6
 27 50  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 739                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      13.964   1.111   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       9.860  -2.003   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       7.636   0.124   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.409  -3.990   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      15.946  -3.166   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      12.499  -0.905   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       9.860   1.732   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0       8.733   3.955   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      12.499   0.635   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.946   0.641   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.964  -1.381   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.869  -0.135   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.946  -0.911   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.104   3.253   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.338   1.495   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.642   2.868   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.115  -1.040   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.115   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.440  -2.846   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.624   3.009   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.805   4.624   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.121   3.112   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.149   1.917   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.572   4.551   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.629   2.161   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.052   4.795   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.080   3.600   0.000  0.00  0.00           C+0
HETATM   28  H   UNK     0      12.309   1.852   0.000  0.00  0.00           H+0
CONECT    1    9   12                                                       
CONECT    2   13                                                            
CONECT    3   15                                                            
CONECT    4   19                                                            
CONECT    5   19                                                            
CONECT    6    9   11   13                                                  
CONECT    7   10   14   15                                                  
CONECT    8   14   16                                                       
CONECT    9    1    6   10   28                                             
CONECT   10    7    9   13                                                  
CONECT   11    6   12   19                                                  
CONECT   12    1   11   17   18                                             
CONECT   13    2    6   10                                                  
CONECT   14    7    8   20   21                                             
CONECT   15    3    7   16                                                  
CONECT   16    8   15   22                                                  
CONECT   17   12                                                            
CONECT   18   12                                                            
CONECT   19    4    5   11                                                  
CONECT   20   14                                                            
CONECT   21   14                                                            
CONECT   22   16   23   24                                                  
CONECT   23   22   25                                                       
CONECT   24   22   26                                                       
CONECT   25   23   27                                                       
CONECT   26   24   27                                                       
CONECT   27   25   26                                                       
CONECT   28    9                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

COMPND    HMDB0014877
HETATM    1  C1  UNL     1      -3.637   0.520  -2.308  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.708   0.238  -0.820  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.142   0.304  -0.331  1.00  0.00           C  
HETATM    4  S1  UNL     1      -2.690   1.443   0.081  1.00  0.00           S  
HETATM    5  C4  UNL     1      -2.236   0.300   1.343  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.876   0.006   1.773  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.307   0.304   1.110  1.00  0.00           N  
HETATM    8  C6  UNL     1       1.436   1.040   1.747  1.00  0.00           C  
HETATM    9  O1  UNL     1       1.611   1.106   2.967  1.00  0.00           O  
HETATM   10  C7  UNL     1       2.255   1.641   0.694  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.680   1.241   0.679  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.271   0.614   1.749  1.00  0.00           C  
HETATM   13  C10 UNL     1       5.624   0.265   1.684  1.00  0.00           C  
HETATM   14  C11 UNL     1       6.343   0.555   0.549  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.754   1.181  -0.520  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.434   1.525  -0.465  1.00  0.00           C  
HETATM   17  N2  UNL     1       1.594   1.244  -0.542  1.00  0.00           N  
HETATM   18  C14 UNL     1       0.870   0.019  -0.148  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.048  -0.413  -1.285  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.949  -1.073   0.137  1.00  0.00           C  
HETATM   21  C17 UNL     1      -1.314  -1.383   1.635  1.00  0.00           C  
HETATM   22  O2  UNL     1      -1.025  -2.508   2.128  1.00  0.00           O  
HETATM   23  N3  UNL     1      -2.254  -0.974   0.672  1.00  0.00           N  
HETATM   24  C18 UNL     1      -3.115  -1.046  -0.434  1.00  0.00           C  
HETATM   25  C19 UNL     1      -4.191  -2.058  -0.077  1.00  0.00           C  
HETATM   26  O3  UNL     1      -4.217  -2.655   1.017  1.00  0.00           O  
HETATM   27  O4  UNL     1      -5.179  -2.325  -1.006  1.00  0.00           O  
HETATM   28  H1  UNL     1      -2.847  -0.087  -2.748  1.00  0.00           H  
HETATM   29  H2  UNL     1      -4.647   0.297  -2.710  1.00  0.00           H  
HETATM   30  H3  UNL     1      -3.380   1.583  -2.426  1.00  0.00           H  
HETATM   31  H4  UNL     1      -5.424   1.334  -0.029  1.00  0.00           H  
HETATM   32  H5  UNL     1      -5.819  -0.080  -1.096  1.00  0.00           H  
HETATM   33  H6  UNL     1      -5.202  -0.331   0.575  1.00  0.00           H  
HETATM   34  H7  UNL     1      -2.945   0.229   2.219  1.00  0.00           H  
HETATM   35  H8  UNL     1      -0.788   0.301   2.917  1.00  0.00           H  
HETATM   36  H9  UNL     1       2.186   2.777   0.729  1.00  0.00           H  
HETATM   37  H10 UNL     1       3.726   0.378   2.642  1.00  0.00           H  
HETATM   38  H11 UNL     1       6.040  -0.220   2.537  1.00  0.00           H  
HETATM   39  H12 UNL     1       7.377   0.276   0.527  1.00  0.00           H  
HETATM   40  H13 UNL     1       6.332   1.405  -1.411  1.00  0.00           H  
HETATM   41  H14 UNL     1       3.967   2.027  -1.322  1.00  0.00           H  
HETATM   42  H15 UNL     1       2.252   0.938  -1.283  1.00  0.00           H  
HETATM   43  H16 UNL     1       0.721  -0.491  -2.221  1.00  0.00           H  
HETATM   44  H17 UNL     1      -0.762   0.233  -1.606  1.00  0.00           H  
HETATM   45  H18 UNL     1      -0.267  -1.482  -1.124  1.00  0.00           H  
HETATM   46  H19 UNL     1       2.861  -0.893  -0.426  1.00  0.00           H  
HETATM   47  H20 UNL     1       1.470  -2.022  -0.214  1.00  0.00           H  
HETATM   48  H21 UNL     1       2.096  -1.196   1.221  1.00  0.00           H  
HETATM   49  H22 UNL     1      -2.636  -1.469  -1.367  1.00  0.00           H  
HETATM   50  H23 UNL     1      -4.901  -2.619  -1.930  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3    4   24
CONECT    3   31   32   33
CONECT    4    5
CONECT    5    6   23   34
CONECT    6    7   21   35
CONECT    7    8   18
CONECT    8    9    9   10
CONECT   10   11   17   36
CONECT   11   12   12   16
CONECT   12   13   37
CONECT   13   14   14   38
CONECT   14   15   39
CONECT   15   16   16   40
CONECT   16   41
CONECT   17   18   42
CONECT   18   19   20
CONECT   19   43   44   45
CONECT   20   46   47   48
CONECT   21   22   22   23
CONECT   23   24
CONECT   24   25   49
CONECT   25   26   26   27
CONECT   27   50
END

HMDB0014877
     RDKit          3D
Hetacillin
 50 53  0  0  0  0  0  0  0  0999 V2000
   -3.6365    0.5196   -2.3076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7077    0.2382   -0.8203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1415    0.3040   -0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6899    1.4433    0.0813 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2360    0.3001    1.3428 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8761    0.0058    1.7726 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3074    0.3044    1.1095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4363    1.0402    1.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6109    1.1062    2.9668 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2546    1.6410    0.6942 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6803    1.2409    0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2706    0.6141    1.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6239    0.2646    1.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3427    0.5549    0.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7541    1.1809   -0.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4336    1.5253   -0.4650 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5936    1.2436   -0.5415 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701    0.0191   -0.1477 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0481   -0.4126   -1.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9493   -1.0734    0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3144   -1.3828    1.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0250   -2.5082    2.1281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538   -0.9743    0.6719 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1153   -1.0460   -0.4344 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1910   -2.0579   -0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2173   -2.6554    1.0172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1794   -2.3246   -1.0064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8473   -0.0874   -2.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6473    0.2974   -2.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3800    1.5829   -2.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4241    1.3343   -0.0292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8186   -0.0800   -1.0960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2021   -0.3314    0.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9451    0.2293    2.2194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7884    0.3012    2.9166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1862    2.7765    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7259    0.3784    2.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0400   -0.2195    2.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3773    0.2759    0.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3316    1.4046   -1.4111 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9668    2.0270   -1.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2521    0.9381   -1.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7208   -0.4906   -2.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7617    0.2326   -1.6057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2672   -1.4825   -1.1239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8615   -0.8927   -0.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4699   -2.0215   -0.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0957   -1.1961    1.2215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6363   -1.4689   -1.3675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9011   -2.6185   -1.9297 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
 10 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
  6 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 24  2  1  0
 23  5  1  0
 18  7  1  0
 16 11  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  3 31  1  0
  3 32  1  0
  3 33  1  0
  5 34  1  1
  6 35  1  1
 10 36  1  1
 12 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 19 43  1  0
 19 44  1  0
 19 45  1  0
 20 46  1  0
 20 47  1  0
 20 48  1  0
 24 49  1  6
 27 50  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(2S,5R,6R)-6-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
6beta-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanic acid	ChEBI
Hetacilina	ChEBI
Hetacilline	ChEBI
Hetacillinum	ChEBI
Versapen	Kegg
(2S,5R,6R)-6-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
6b-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanate	Generator
6b-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanic acid	Generator
6beta-[(4R)-2,2-Dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanate	Generator
6Β-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanate	Generator
6Β-[(4R)-2,2-dimethyl-5-oxo-4-phenylimidazolidin-1-yl]penicillanic acid	Generator
Hetacillin, monosodium salt, (2S-(2alpha,5alpha,6beta(s*)))-isomer	HMDB
Hetacillin, monosodium salt, (2S-(2alpha,5alpha,6beta))-isomer	HMDB
Phenazacillin	HMDB
Hetacillin, (2S-(2alpha,5alpha,6alpha))-isomer	HMDB
Hetacillin, aluminum salt (3:1), (2S-(2alpha,5alpha,6beta(s*)))-isomer	HMDB
Hetacillin, monopotassium salt, (2S-(2alpha,5alpha,6beta(s*)))-isomer	HMDB

Chemical Formula

C₁₉H₂₃N₃O₄S

Average Molecular Weight

389.469

Monoisotopic Molecular Weight

389.140926929

IUPAC Name

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

Traditional Name

hetacillin

CAS Registry Number

3511-16-8

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2N1C(=O)[C@H](NC1(C)C)C1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C19H23N3O4S/c1-18(2)13(17(25)26)21-15(24)12(16(21)27-18)22-14(23)11(20-19(22,3)4)10-8-6-5-7-9-10/h5-9,11-13,16,20H,1-4H3,(H,25,26)/t11-,12-,13+,16-/m1/s1

InChI Key

DXVUYOAEDJXBPY-NFFDBFGFSA-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
Phenylimidazolidine
Alpha-amino acid or derivatives
Monocyclic benzene moiety
Imidazolidinone
Benzenoid
Imidazolidine
Thiazolidine
Tertiary carboxylic acid amide
Amino acid or derivatives
Azetidine
Amino acid
Carboxamide group
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Azacycle
Dialkylthioether
Monocarboxylic acid or derivatives
Hemithioaminal
Thioether
Secondary amine
Amine
Organic oxygen compound
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:5683 )

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

Membrane (HMDB: HMDB0014877)

Source

Exogenous

Exogenous (HMDB: HMDB0014877)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	190 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.51 g/L	Not Available
LogP	1.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	189.584	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001511

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.51 g/L	ALOGPS
logP	0.85	ALOGPS
logP	-0.015	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	3.63	ChemAxon
pKa (Strongest Basic)	5.47	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	89.95 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	99.9 m³·mol⁻¹	ChemAxon
Polarizability	39.58 Å³	ChemAxon
Number of Rings	4	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]+	187.239	31661259
DarkChem	[M-H]-	178.026	31661259
DeepCCS	[M-2H]-	216.67	30932474
DeepCCS	[M+Na]+	192.094	30932474
AllCCS	[M+H]+	188.3	32859911
AllCCS	[M+H-H2O]+	186.0	32859911
AllCCS	[M+NH4]+	190.4	32859911
AllCCS	[M+Na]+	191.0	32859911
AllCCS	[M-H]-	189.8	32859911
AllCCS	[M+Na-2H]-	190.0	32859911
AllCCS	[M+HCOO]-	190.4	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.	4.15 minutes	32390414
Predicted by Siyang on May 30, 2022	12.2585 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.97 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2172.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	212.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	142.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	151.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	78.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	357.2 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	442.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	66.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	909.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	428.2 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	1255.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	257.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	332.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	200.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	186.5 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	28.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hetacillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2N1C(=O)[C@H](NC1(C)C)C1=CC=CC=C1)C(O)=O	4399.9	Standard polar	33892256
Hetacillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2N1C(=O)[C@H](NC1(C)C)C1=CC=CC=C1)C(O)=O	2767.1	Standard non polar	33892256
Hetacillin	[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2N1C(=O)[C@H](NC1(C)C)C1=CC=CC=C1)C(O)=O	3215.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hetacillin,1TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)NC3(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2798.6	Semi standard non polar	33892256
Hetacillin,1TMS,isomer #2	CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)N([Si](C)(C)C)C3(C)C)C(=O)N2[C@H]1C(=O)O	2746.6	Semi standard non polar	33892256
Hetacillin,2TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)N([Si](C)(C)C)C3(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2726.3	Semi standard non polar	33892256
Hetacillin,2TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)N([Si](C)(C)C)C3(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	2948.7	Standard non polar	33892256
Hetacillin,2TMS,isomer #1	CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)N([Si](C)(C)C)C3(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C	3460.3	Standard polar	33892256
Hetacillin,1TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)NC3(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3016.6	Semi standard non polar	33892256
Hetacillin,1TBDMS,isomer #2	CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)N([Si](C)(C)C(C)(C)C)C3(C)C)C(=O)N2[C@H]1C(=O)O	2975.3	Semi standard non polar	33892256
Hetacillin,2TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)N([Si](C)(C)C(C)(C)C)C3(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3149.2	Semi standard non polar	33892256
Hetacillin,2TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)N([Si](C)(C)C(C)(C)C)C3(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3389.5	Standard non polar	33892256
Hetacillin,2TBDMS,isomer #1	CC1(C)S[C@@H]2[C@H](N3C(=O)[C@@H](C4=CC=CC=C4)N([Si](C)(C)C(C)(C)C)C3(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C	3623.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Hetacillin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0597-7943000000-e629ee26cef364aec2d7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hetacillin GC-MS (1 TMS) - 70eV, Positive	splash10-00xu-9143300000-6fa9d2cea0ccf74ae209	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hetacillin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Hetacillin 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 - Hetacillin 10V, Positive-QTOF	splash10-03di-0902000000-912bca5479e6d278d37f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hetacillin 20V, Positive-QTOF	splash10-03di-0910000000-9531e0f64a1e00ef3488	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hetacillin 40V, Positive-QTOF	splash10-0btc-3900000000-a2875c749c7af28b9466	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hetacillin 10V, Negative-QTOF	splash10-0002-0092000000-1d1ea0d542ee0060a90d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hetacillin 20V, Negative-QTOF	splash10-0002-0093000000-fea6a48a167d8b663fb0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hetacillin 40V, Negative-QTOF	splash10-00c1-9521000000-936ddaa0d3690efedc74	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hetacillin 10V, Positive-QTOF	splash10-0006-0009000000-3ec18c91e5d64861d13d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hetacillin 20V, Positive-QTOF	splash10-0006-0239000000-4f0de60022c322c73392	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hetacillin 40V, Positive-QTOF	splash10-0006-5911000000-2d78f162743e488a050d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hetacillin 10V, Negative-QTOF	splash10-000i-0009000000-e24e100bd150f5e8fbba	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hetacillin 20V, Negative-QTOF	splash10-052r-0094000000-0aaabd2b493b44418bbe	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hetacillin 40V, Negative-QTOF	splash10-0zg3-3791000000-daeb0fa6db82a3343e56	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)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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 DB00739	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00739	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00739

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

391616

KEGG Compound ID

C11729

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Hetacillin

METLIN ID

Not Available

PubChem Compound

443387

PDB ID

Not Available

ChEBI ID

5683

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 Hetacillin (HMDB0014877)

MOL for HMDB0014877 (Hetacillin)

3D MOL for HMDB0014877 (Hetacillin)

3D SDF for HMDB0014877 (Hetacillin)

3D-SDF for HMDB0014877 (Hetacillin)

PDB for HMDB0014877 (Hetacillin)

3D PDB for HMDB0014877 (Hetacillin)

SMILES for HMDB0014877 (Hetacillin)

INCHI for HMDB0014877 (Hetacillin)

Structure for HMDB0014877 (Hetacillin)

3D Structure for HMDB0014877 (Hetacillin)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra