MiMeDB: Showing metabocard for (7R)-7-(4-carboxybutanamido)cephalosporanate (MMDBc0054076)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:51:28 UTC

Update Date

2022-09-01 02:27:00 UTC

Metabolite ID

MMDBc0054076

Metabolite Identification

Common Name

(7R)-7-(4-carboxybutanamido)cephalosporanate

Description

(7R)-7-(4-carboxybutanamido)cephalosporanic acid, also known as 7-glutarylaminocephalosporanate or GL-7-aca, belongs to the class of organic compounds known as cephalosporin 3'-esters. These are cephalosporins that are esterified at the 3'-position (7R)-7-(4-carboxybutanamido)cephalosporanic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05041401422D          

 28 29  0  0  1  0            999 V2000
   -6.8082    3.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864    4.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2281    4.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2009    4.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8446    2.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342    3.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2248    3.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0477    2.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9425    4.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9153    4.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570    3.1051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4643    2.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8705    2.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4539    3.3187    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6778    1.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9425    3.5176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6674    2.5218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4384    2.2510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570    4.7551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298    4.7551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9153    3.5176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4580    1.5938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0945    0.9280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4747    1.2978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4279    3.2614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373    3.9020    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025    2.6029    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0414    4.0331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  7  1  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 12  8  2  0  0  0  0
 13 11  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16  9  2  0  0  0  0
 11 16  1  6  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18  7  2  0  0  0  0
  9 19  1  4  0  0  0
 20 10  2  0  0  0  0
 21 10  1  0  0  0  0
 22 13  2  0  0  0  0
 23 15  2  0  0  0  0
 24 15  1  0  0  0  0
 25  5  1  0  0  0  0
 25  7  1  0  0  0  0
 26  6  1  0  0  0  0
 26 14  1  0  0  0  0
 11 27  1  1  0  0  0
 14 28  1  1  0  0  0
M  END


  Mrv0541 05041401422D          

 28 29  0  0  1  0            999 V2000
   -6.8082    3.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864    4.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2281    4.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2009    4.7551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8446    2.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342    3.6885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2248    3.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0477    2.8916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9425    4.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9153    4.3426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570    3.1051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4643    2.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8705    2.3082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4539    3.3187    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6778    1.5114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9425    3.5176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6674    2.5218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4384    2.2510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6570    4.7551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6298    4.7551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9153    3.5176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4580    1.5938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0945    0.9280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4747    1.2978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4279    3.2614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0373    3.9020    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0025    2.6029    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0414    4.0331    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  7  1  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 12  8  2  0  0  0  0
 13 11  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16  9  2  0  0  0  0
 11 16  1  6  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18  7  2  0  0  0  0
  9 19  1  4  0  0  0
 20 10  2  0  0  0  0
 21 10  1  0  0  0  0
 22 13  2  0  0  0  0
 23 15  2  0  0  0  0
 24 15  1  0  0  0  0
 25  5  1  0  0  0  0
 25  7  1  0  0  0  0
 26  6  1  0  0  0  0
 26 14  1  0  0  0  0
 11 27  1  1  0  0  0
 14 28  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054076

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@@]2([H])N=C(O)CCCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H18N2O8S/c1-7(18)25-5-8-6-26-14-11(13(22)17(14)12(8)15(23)24)16-9(19)3-2-4-10(20)21/h11,14H,2-6H2,1H3,(H,16,19)(H,20,21)(H,23,24)/t11-,14-/m1/s1

> <INCHI_KEY>
IXUSDMGLUJZNFO-BXUZGUMPSA-N

> <FORMULA>
C15H18N2O8S

> <MOLECULAR_WEIGHT>
386.377

> <EXACT_MASS>
386.078386252

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
37.40951004928921

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6R,7R)-3-[(acetyloxy)methyl]-7-[(4-carboxy-1-hydroxybutylidene)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

> <ALOGPS_LOGP>
-0.19

> <JCHEM_LOGP>
-0.6419127470000006

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.08436689826081

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4543336855272755

> <JCHEM_PKA_STRONGEST_BASIC>
0.45410444831944624

> <JCHEM_POLAR_SURFACE_AREA>
153.79999999999998

> <JCHEM_REFRACTIVITY>
88.19819999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6R,7R)-3-[(acetyloxy)methyl]-7-[(4-carboxy-1-hydroxybutylidene)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-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  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+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  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   26  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+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    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    9                                                       
CONECT    4    2   10                                                       
CONECT    5    8   25                                                       
CONECT    6    8   26                                                       
CONECT    7    1   18   25                                                  
CONECT    8    5    6   12                                                  
CONECT    9    3   16   19                                                  
CONECT   10    4   20   21                                                  
CONECT   11   13   14   16   27                                             
CONECT   12    8   15   17                                                  
CONECT   13   11   17   22                                                  
CONECT   14   11   17   26   28                                             
CONECT   15   12   23   24                                                  
CONECT   16    9   11                                                       
CONECT   17   12   13   14                                                  
CONECT   18    7                                                            
CONECT   19    9                                                            
CONECT   20   10                                                            
CONECT   21   10                                                            
CONECT   22   13                                                            
CONECT   23   15                                                            
CONECT   24   15                                                            
CONECT   25    5    7                                                       
CONECT   26    6   14                                                       
CONECT   27   11                                                            
CONECT   28   14                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

Synonyms

Value	Source
(7R)-7-(4-Carboxybutanamido)cephalosporanate	ChEBI
7-Glutarylaminocephalosporanate	ChEBI
7BETA-(4CARBOXYBUTANAMIDO) cephalosporanIC ACID	ChEBI
GL-7-Aca	ChEBI
Glutaryl-7-aca	ChEBI
Glutaryl-7-aminocephalosporanic acid	ChEBI
7-Glutarylaminocephalosporanic acid	Generator
7b-(4CARBOXYBUTANAMIDO) cephalosporanate	Generator
7b-(4CARBOXYBUTANAMIDO) cephalosporanic acid	Generator
7beta-(4CARBOXYBUTANAMIDO) cephalosporanate	Generator
7Β-(4carboxybutanamido) cephalosporanate	Generator
7Β-(4carboxybutanamido) cephalosporanic acid	Generator
Glutaryl-7-aminocephalosporanate	Generator

Molecular Formula

C₁₅H₁₈N₂O₈S

Average Mass

386.377

Monoisotopic Mass

386.078386252

IUPAC Name

(6R,7R)-3-[(acetyloxy)methyl]-7-[(4-carboxy-1-hydroxybutylidene)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Traditional Name

(6R,7R)-3-[(acetyloxy)methyl]-7-[(4-carboxy-1-hydroxybutylidene)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@@]2([H])N=C(O)CCCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C15H18N2O8S/c1-7(18)25-5-8-6-26-14-11(13(22)17(14)12(8)15(23)24)16-9(19)3-2-4-10(20)21/h11,14H,2-6H2,1H3,(H,16,19)(H,20,21)(H,23,24)/t11-,14-/m1/s1

InChI Key

IXUSDMGLUJZNFO-BXUZGUMPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cephalosporin 3'-esters. These are cephalosporins that are esterified at the 3'-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Cephalosporin 3'-esters

Alternative Parents

Substituents

Cephalosporin 3'-ester
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
Meta-thiazine
Fatty amide
N-acyl-amine
Fatty acyl
Tertiary carboxylic acid amide
Azetidine
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Carboxylic acid
Carboxylic acid derivative
Azacycle
Thioether
Hemithioaminal
Dialkylthioether
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

cephalosporin (CHEBI:41425 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.29 g/L	ALOGPS
logP	-0.19	ALOGPS
logP	-0.64	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.45	ChemAxon
pKa (Strongest Basic)	0.45	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	153.8 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	88.2 m³·mol⁻¹	ChemAxon
Polarizability	37.41 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	1	Human ; Human subgingival plaque
Bacteria	Proteobacteria	3	Human ; Human subgingival plaque

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C15666

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

446570

PDB ID

Not Available

ChEBI ID

41425

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (7R)-7-(4-carboxybutanamido)cephalosporanate (MMDBc0054076)

MOL for #<Metabolite:0x00005645c567a550>

3D MOL for #<Metabolite:0x00005645c567a550>

3D SDF for #<Metabolite:0x00005645c567a550>

3D-SDF for #<Metabolite:0x00005645c567a550>

PDB for #<Metabolite:0x00005645c567a550>

3D PDB for #<Metabolite:0x00005645c567a550>

SMILES for #<Metabolite:0x00005645c567a550>

INCHI for #<Metabolite:0x00005645c567a550>

Structure for #<Metabolite:0x00005645c567a550>

3D Structure for #<Metabolite:0x00005645c567a550>