MiMeDB: Showing metabocard for Isopenicillin N (MMDBc0053378)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 21:22:38 UTC

Update Date

2024-10-13 10:28:05 UTC

Metabolite ID

MMDBc0053378

Metabolite Identification

Common Name

Isopenicillin N

Description

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05041405552D          

 28 29  0  0  1  0            999 V2000
   11.1332    7.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0668    7.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6429    5.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9284    4.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3573    4.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2139    5.3469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0718    5.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5008    5.3469    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9605    6.6222    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2976    5.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7143    6.1438    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4995    4.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7844    6.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4413    7.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2139    6.1719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7863    4.9344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5112    5.9303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0718    6.1719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7101    4.4189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7850    5.3469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4995    4.1094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1589    7.4004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2337    5.9735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6711    6.9677    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2139    4.5219    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6084    4.5290    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2961    7.3759    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8938    6.2300    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
  9 13  1  6  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  9  1  0  0  0  0
  6 15  1  6  0  0  0
 16  7  2  0  0  0  0
  8 16  1  1  0  0  0
 17  9  1  0  0  0  0
 17 10  1  0  0  0  0
 17 11  1  0  0  0  0
  7 18  1  4  0  0  0
 19 10  2  0  0  0  0
 20 12  2  0  0  0  0
 21 12  1  0  0  0  0
 22 13  2  0  0  0  0
 23 13  1  0  0  0  0
 24 11  1  0  0  0  0
 24 14  1  0  0  0  0
  6 25  1  6  0  0  0
  8 26  1  6  0  0  0
  9 27  1  1  0  0  0
 11 28  1  6  0  0  0
M  END

  Mrv0541 05041405552D          

 28 29  0  0  1  0            999 V2000
   11.1332    7.7127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0668    7.9984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6429    5.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9284    4.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3573    4.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2139    5.3469    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0718    5.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5008    5.3469    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9605    6.6222    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.2976    5.1334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7143    6.1438    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4995    4.9344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7844    6.6654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4413    7.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2139    6.1719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7863    4.9344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5112    5.9303    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0718    6.1719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7101    4.4189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7850    5.3469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4995    4.1094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1589    7.4004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2337    5.9735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6711    6.9677    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2139    4.5219    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6084    4.5290    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2961    7.3759    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8938    6.2300    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
  9 13  1  6  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  9  1  0  0  0  0
  6 15  1  6  0  0  0
 16  7  2  0  0  0  0
  8 16  1  1  0  0  0
 17  9  1  0  0  0  0
 17 10  1  0  0  0  0
 17 11  1  0  0  0  0
  7 18  1  4  0  0  0
 19 10  2  0  0  0  0
 20 12  2  0  0  0  0
 21 12  1  0  0  0  0
 22 13  2  0  0  0  0
 23 13  1  0  0  0  0
 24 11  1  0  0  0  0
 24 14  1  0  0  0  0
  6 25  1  6  0  0  0
  8 26  1  6  0  0  0
  9 27  1  1  0  0  0
 11 28  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0053378

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](N)(CCCC(O)=N[C@]1([H])C(=O)N2[C@]1([H])SC(C)(C)[C@]2([H])C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H21N3O6S/c1-14(2)9(13(22)23)17-10(19)8(11(17)24-14)16-7(18)5-3-4-6(15)12(20)21/h6,8-9,11H,3-5,15H2,1-2H3,(H,16,18)(H,20,21)(H,22,23)/t6-,8+,9-,11+/m0/s1

> <INCHI_KEY>
MIFYHUACUWQUKT-GTQWGBSQSA-N

> <FORMULA>
C14H21N3O6S

> <MOLECULAR_WEIGHT>
359.398

> <EXACT_MASS>
359.115106109

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
35.261581336218

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.94

> <JCHEM_LOGP>
-2.579195653564068

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
3.584446292870892

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.8261052662223594

> <JCHEM_PKA_STRONGEST_BASIC>
9.529587376751913

> <JCHEM_POLAR_SURFACE_AREA>
153.51999999999998

> <JCHEM_REFRACTIVITY>
83.57259999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5R,6R)-6-{[(5S)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
HETATM   25  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   12   15   25                                             
CONECT    7    5   16   18                                                  
CONECT    8   10   11   16   26                                             
CONECT    9   13   14   17   27                                             
CONECT   10    8   17   19                                                  
CONECT   11    8   17   24   28                                             
CONECT   12    6   20   21                                                  
CONECT   13    9   22   23                                                  
CONECT   14    1    2    9   24                                             
CONECT   15    6                                                            
CONECT   16    7    8                                                       
CONECT   17    9   10   11                                                  
CONECT   18    7                                                            
CONECT   19   10                                                            
CONECT   20   12                                                            
CONECT   21   12                                                            
CONECT   22   13                                                            
CONECT   23   13                                                            
CONECT   24   11   14                                                       
CONECT   25    6                                                            
CONECT   26    8                                                            
CONECT   27    9                                                            
CONECT   28   11                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

Synonyms

Value	Source
(2S,5R,6R)-6-[(5S)-5-Amino-5-carboxypentanamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
(2S,5R,6R)-6-[(5S)-5-Amino-5-carboxypentanamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
Penicillin N, (2S-(2alpha,5alpha,6beta(r*)))-isomer	MeSH
Penicillin N, monopotassium salt, (2S-(2alpha,5alpha,6beta(r*)))-isomer	MeSH
Penicillin N	MeSH
Penicillin N, potassium salt, (2S-(2alpha,5alpha,6beta(r*)))-isomer	MeSH
D-4-amino-4-Carboxybutyl penicillanic acid	MeSH
Adicillin	MeSH
Cephalosporin N	MeSH
Penicillin N, potassium salt, (2S-(2alpha,5alpha,6beta(s*)))-isomer	MeSH

Molecular Formula

C₁₄H₂₁N₃O₆S

Average Mass

359.398

Monoisotopic Mass

359.115106109

IUPAC Name

(2S,5R,6R)-6-{[(5S)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

(2S,5R,6R)-6-{[(5S)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@](N)(CCCC(O)=N[C@]1([H])C(=O)N2[C@]1([H])SC(C)(C)[C@]2([H])C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C14H21N3O6S/c1-14(2)9(13(22)23)17-10(19)8(11(17)24-14)16-7(18)5-3-4-6(15)12(20)21/h6,8-9,11H,3-5,15H2,1-2H3,(H,16,18)(H,20,21)(H,22,23)/t6-,8+,9-,11+/m0/s1

InChI Key

MIFYHUACUWQUKT-GTQWGBSQSA-N

Chemical Taxonomy

Functional Ontology

Physical Properties

Spectra

Biological Properties

Human Proteins and Enzymes

Human Pathways

Metabolic Reactions

Health Effects and Bioactivity

Microbial Sources

Exposure Sources

Host Biospecimen and Location

External Links

References

Showing metabocard for Isopenicillin N (MMDBc0053378)

MOL for #<Metabolite:0x00007fdf49e29840>

3D MOL for #<Metabolite:0x00007fdf49e29840>

3D SDF for #<Metabolite:0x00007fdf49e29840>

3D-SDF for #<Metabolite:0x00007fdf49e29840>

PDB for #<Metabolite:0x00007fdf49e29840>

3D PDB for #<Metabolite:0x00007fdf49e29840>

SMILES for #<Metabolite:0x00007fdf49e29840>

INCHI for #<Metabolite:0x00007fdf49e29840>

Structure for #<Metabolite:0x00007fdf49e29840>

3D Structure for #<Metabolite:0x00007fdf49e29840>