MiMeDB: Showing metabocard for (7R)-7-aminocephalosporanate (MMDBc0054077)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:51:29 UTC

Update Date

2022-09-01 02:27:01 UTC

Metabolite ID

MMDBc0054077

Metabolite Identification

Common Name

(7R)-7-aminocephalosporanate

Description

7beta-aminocephalosporanic acid, also known as (7R)-7-aminocephalosporanate or 7-ACA, belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. The alpha,beta-unsaturated monocarboxylic acid that is the active nucleus for the synthesis of cephalosporins and intermediates. 7beta-aminocephalosporanic acid is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05031422152D          

 20 21  0  0  1  0            999 V2000
    5.9773    1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8339    2.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    0.9760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2628    2.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655    0.9760    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4049    2.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655    1.8010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905    0.9760    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4049    3.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2821    0.3926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905    1.8010    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2628    3.0385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2821    2.3843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6905    3.4510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1194    3.4510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5483    1.8010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4049    0.5635    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033    1.2917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4769    0.1791    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
  6 11  1  6  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  4  2  0  0  0  0
 14  8  2  0  0  0  0
 15 10  2  0  0  0  0
 16 10  1  0  0  0  0
 17  2  1  0  0  0  0
 17  4  1  0  0  0  0
 18  3  1  0  0  0  0
 18  9  1  0  0  0  0
  6 19  1  1  0  0  0
  9 20  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054077

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@@]1(N)C(=O)N2C(C(O)=O)=C(COC(C)=O)CS[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C10H12N2O5S/c1-4(13)17-2-5-3-18-9-6(11)8(14)12(9)7(5)10(15)16/h6,9H,2-3,11H2,1H3,(H,15,16)/t6-,9-/m1/s1

> <INCHI_KEY>
HSHGZXNAXBPPDL-HZGVNTEJSA-N

> <FORMULA>
C10H12N2O5S

> <MOLECULAR_WEIGHT>
272.278

> <EXACT_MASS>
272.046692194

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
25.569219139654535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-1.02

> <JCHEM_LOGP>
-3.8148884752885754

> <ALOGPS_LOGS>
-1.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.621162092024626

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4190428887385216

> <JCHEM_PKA_STRONGEST_BASIC>
7.385654668675919

> <JCHEM_POLAR_SURFACE_AREA>
109.93

> <JCHEM_REFRACTIVITY>
62.73840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.72e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7β-aminocephalosporanic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-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  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  S   UNK     0       0.000   0.000   0.000  0.00  0.00           S+0
HETATM   19  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2    5   17                                                       
CONECT    3    5   18                                                       
CONECT    4    1   13   17                                                  
CONECT    5    2    3    7                                                  
CONECT    6    8    9   11   19                                             
CONECT    7    5   10   12                                                  
CONECT    8    6   12   14                                                  
CONECT    9    6   12   18   20                                             
CONECT   10    7   15   16                                                  
CONECT   11    6                                                            
CONECT   12    7    8    9                                                  
CONECT   13    4                                                            
CONECT   14    8                                                            
CONECT   15   10                                                            
CONECT   16   10                                                            
CONECT   17    2    4                                                       
CONECT   18    3    9                                                       
CONECT   19    6                                                            
CONECT   20    9                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

Synonyms

Value	Source
(7R)-7-Aminocephalosporanate	ChEBI
7-ACA	ChEBI
7-Aminocephalosporanic acid	ChEBI
7-Aminocephalosporinic acid	ChEBI
(7R)-7-Aminocephalosporanic acid	Generator
7-Aminocephalosporanate	Generator
7-Aminocephalosporinate	Generator
7b-Aminocephalosporanate	Generator
7b-Aminocephalosporanic acid	Generator
7beta-Aminocephalosporanate	Generator
7Β-aminocephalosporanate	Generator
7Β-aminocephalosporanic acid	Generator
7-ACA CPD	MeSH

Molecular Formula

C₁₀H₁₂N₂O₅S

Average Mass

272.278

Monoisotopic Mass

272.046692194

IUPAC Name

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

Traditional Name

7β-aminocephalosporanic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]1(N)C(=O)N2C(C(O)=O)=C(COC(C)=O)CS[C@]12[H]

InChI Identifier

InChI=1S/C10H12N2O5S/c1-4(13)17-2-5-3-18-9-6(11)8(14)12(9)7(5)10(15)16/h6,9H,2-3,11H2,1H3,(H,15,16)/t6-,9-/m1/s1

InChI Key

HSHGZXNAXBPPDL-HZGVNTEJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Cephem
Meta-thiazine
Dicarboxylic acid or derivatives
Beta-lactam
Tertiary carboxylic acid amide
Azetidine
Amino acid
Carboxamide group
Carboxylic acid ester
Lactam
Azacycle
Carboxylic acid
Organoheterocyclic compound
Dialkylthioether
Hemithioaminal
Thioether
Amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organopnictogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Primary amine
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

alpha,beta-unsaturated monocarboxylic acid (CHEBI:2255 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	7.72 g/L	ALOGPS
logP	-1	ALOGPS
logP	-3.8	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.42	ChemAxon
pKa (Strongest Basic)	7.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.93 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	62.74 m³·mol⁻¹	ChemAxon
Polarizability	25.57 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-9080000000-612cfdce5904343c8bc9	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-044i-1590000000-8d548a0e17acf1826179	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9300000000-d92dbfb13f2f0389d65d	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9250000000-cbd7254c13c26c9a7e74	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9100000000-d8a588622ea97950e61d	2016-08-04	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-cceb54c20d73d0aa314b	2016-08-04	View Spectrum

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	Proteobacteria	4	Human ; Human subgingival plaque

Exposure Sources

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

C07756

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441328

PDB ID

Not Available

ChEBI ID

2255

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-aminocephalosporanate (MMDBc0054077)

MOL for #<Metabolite:0x00007fdb4cfe8b28>

3D MOL for #<Metabolite:0x00007fdb4cfe8b28>

3D SDF for #<Metabolite:0x00007fdb4cfe8b28>

3D-SDF for #<Metabolite:0x00007fdb4cfe8b28>

PDB for #<Metabolite:0x00007fdb4cfe8b28>

3D PDB for #<Metabolite:0x00007fdb4cfe8b28>

SMILES for #<Metabolite:0x00007fdb4cfe8b28>

INCHI for #<Metabolite:0x00007fdb4cfe8b28>

Structure for #<Metabolite:0x00007fdb4cfe8b28>

3D Structure for #<Metabolite:0x00007fdb4cfe8b28>