MiMeDB: Showing metabocard for Adipyl-7-aminocephalosporanic acid (MMDBc0002584)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 20:53:32 UTC

Update Date

2022-08-31 06:19:33 UTC

Metabolite ID

MMDBc0002584

Metabolite Identification

Common Name

Adipyl-7-aminocephalosporanic acid

Description

adipyl-7-aminocephalosporanic acid belongs to the class of organic compounds known as cephalosporin 3'-esters. These are cephalosporins that are esterified at the 3'-position. Based on a literature review a significant number of articles have been published on adipyl-7-aminocephalosporanic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305142122532D          

 29 30  0  0  1  0            999 V2000
    5.0034    0.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0256    5.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6889    5.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7401    5.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4033    5.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8471    2.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4669    3.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2170    1.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2638    3.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4546    5.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1178    5.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8835    5.3676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4773    4.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6804    5.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0970    4.5707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2742    4.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1690    5.7801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8939    4.7842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0138    1.6539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4546    4.5426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8323    5.3676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1178    6.6051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0929    6.2956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4877    5.2113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8575    3.8310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6336    2.0237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8835    3.7738    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9912    6.1855    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720    4.5707    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
  5  3  1  0  0  0  0
  8  1  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 13  9  2  0  0  0  0
 14 12  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 10  2  0  0  0  0
 12 17  1  6  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19  8  2  0  0  0  0
 10 20  1  4  0  0  0
 21 11  2  0  0  0  0
 22 11  1  0  0  0  0
 23 14  2  0  0  0  0
 24 16  2  0  0  0  0
 25 16  1  0  0  0  0
 26  6  1  0  0  0  0
 26  8  1  0  0  0  0
 27  7  1  0  0  0  0
 27 15  1  0  0  0  0
 12 28  1  1  0  0  0
 15 29  1  1  0  0  0
M  END


  Mrv1652305142122532D          

 29 30  0  0  1  0            999 V2000
    5.0034    0.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0256    5.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6889    5.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7401    5.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4033    5.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8471    2.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4669    3.1905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2170    1.4404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2638    3.4040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4546    5.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1178    5.7801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8835    5.3676    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4773    4.2009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6804    5.5811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0970    4.5707    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2742    4.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1690    5.7801    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8939    4.7842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0138    1.6539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4546    4.5426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8323    5.3676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1178    6.6051    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0929    6.2956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4877    5.2113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8575    3.8310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6336    2.0237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8835    3.7738    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.9912    6.1855    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720    4.5707    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
  5  3  1  0  0  0  0
  8  1  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 13  9  2  0  0  0  0
 14 12  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  1  0  0  0  0
 17 10  2  0  0  0  0
 12 17  1  6  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
 19  8  2  0  0  0  0
 10 20  1  4  0  0  0
 21 11  2  0  0  0  0
 22 11  1  0  0  0  0
 23 14  2  0  0  0  0
 24 16  2  0  0  0  0
 25 16  1  0  0  0  0
 26  6  1  0  0  0  0
 26  8  1  0  0  0  0
 27  7  1  0  0  0  0
 27 15  1  0  0  0  0
 12 28  1  1  0  0  0
 15 29  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0002584

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H20N2O8S/c1-8(19)26-6-9-7-27-15-12(14(23)18(15)13(9)16(24)25)17-10(20)4-2-3-5-11(21)22/h12,15H,2-7H2,1H3,(H,17,20)(H,21,22)(H,24,25)/t12-,15-/m1/s1

> <INCHI_KEY>
SDDISZQGGKXBSJ-IUODEOHRSA-N

> <FORMULA>
C16H20N2O8S

> <MOLECULAR_WEIGHT>
400.4

> <EXACT_MASS>
400.094036786

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
39.47343256614909

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
-0.03

> <JCHEM_LOGP>
-0.19734408199999975

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.156444538655288

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.49458366688261

> <JCHEM_PKA_STRONGEST_BASIC>
0.5126321601730969

> <JCHEM_POLAR_SURFACE_AREA>
153.79999999999998

> <JCHEM_REFRACTIVITY>
92.79919999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.22e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-21         0                                  
HETATM    1  C   UNK     0       9.340   1.201   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.048  10.020   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.286  10.790   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.381  10.790   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.620  10.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.048   5.265   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.471   5.956   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.738   2.689   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.959   6.354   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.715  10.020   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.953  10.790   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.383  10.020   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.358   7.842   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.870  10.418   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.781   8.532   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.845   8.240   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       4.049  10.790   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       7.269   8.931   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0      11.226   3.087   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.715   8.480   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.287  10.020   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -3.953  12.330   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.640  11.752   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.244   9.728   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      10.934   7.151   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       8.649   3.778   0.000  0.00  0.00           O+0
HETATM   27  S   UNK     0       5.383   7.044   0.000  0.00  0.00           S+0
HETATM   28  H   UNK     0       5.584  11.546   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.241   8.532   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   11                                                       
CONECT    6    9   26                                                       
CONECT    7    9   27                                                       
CONECT    8    1   19   26                                                  
CONECT    9    6    7   13                                                  
CONECT   10    4   17   20                                                  
CONECT   11    5   21   22                                                  
CONECT   12   14   15   17   28                                             
CONECT   13    9   16   18                                                  
CONECT   14   12   18   23                                                  
CONECT   15   12   18   27   29                                             
CONECT   16   13   24   25                                                  
CONECT   17   10   12                                                       
CONECT   18   13   14   15                                                  
CONECT   19    8                                                            
CONECT   20   10                                                            
CONECT   21   11                                                            
CONECT   22   11                                                            
CONECT   23   14                                                            
CONECT   24   16                                                            
CONECT   25   16                                                            
CONECT   26    6    8                                                       
CONECT   27    7   15                                                       
CONECT   28   12                                                            
CONECT   29   15                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

Synonyms

Value	Source
Adipyl-7-aminocephalosporanate	Generator

Molecular Formula

C₁₆H₂₀N₂O₈S

Average Mass

400.4

Monoisotopic Mass

400.094036786

IUPAC Name

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

Traditional Name

(6R,7R)-3-[(acetyloxy)methyl]-7-[(5-carboxy-1-hydroxypentylidene)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)CCCCC(O)=O)C(O)=O

InChI Identifier

InChI=1S/C16H20N2O8S/c1-8(19)26-6-9-7-27-15-12(14(23)18(15)13(9)16(24)25)17-10(20)4-2-3-5-11(21)22/h12,15H,2-7H2,1H3,(H,17,20)(H,21,22)(H,24,25)/t12-,15-/m1/s1

InChI Key

SDDISZQGGKXBSJ-IUODEOHRSA-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

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	-0.03	ALOGPS
logP	-0.2	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.49	ChemAxon
pKa (Strongest Basic)	0.51	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	153.8 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	92.8 m³·mol⁻¹	ChemAxon
Polarizability	39.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

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

8062888

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9887215

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for Adipyl-7-aminocephalosporanic acid (MMDBc0002584)

MOL for #<Metabolite:0x00007f925167d938>

3D MOL for #<Metabolite:0x00007f925167d938>

3D SDF for #<Metabolite:0x00007f925167d938>

3D-SDF for #<Metabolite:0x00007f925167d938>

PDB for #<Metabolite:0x00007f925167d938>

3D PDB for #<Metabolite:0x00007f925167d938>

SMILES for #<Metabolite:0x00007f925167d938>

INCHI for #<Metabolite:0x00007f925167d938>

Structure for #<Metabolite:0x00007f925167d938>

3D Structure for #<Metabolite:0x00007f925167d938>