Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2012-09-06 15:16:52 UTC |
---|
Update Date | 2022-03-07 02:52:04 UTC |
---|
HMDB ID | HMDB0015685 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | Azidocillin |
---|
Description | Azidocillin is only found in individuals that have used or taken this drug. It is a penicillin antibiotic similir to ampicillin.By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Azidocillin inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Azidocillin interferes with an autolysin inhibitor. |
---|
Structure | [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N=[N+]=[N-])C1=CC=CC=C1)C(O)=O InChI=1S/C16H17N5O4S/c1-16(2)11(15(24)25)21-13(23)10(14(21)26-16)18-12(22)9(19-20-17)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,22)(H,24,25)/t9-,10-,11+,14-/m1/s1 |
---|
Synonyms | Value | Source |
---|
(2S,5R,6R)-6-{[(2R)-2-azido-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | ChEBI | Azidocilina | ChEBI | Azidocilline | ChEBI | Azidocillinum | ChEBI | D-(-)-(alpha-Azidobenzyl)penicillin | ChEBI | (2S,5R,6R)-6-{[(2R)-2-azido-2-phenylacetyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | Generator | D-(-)-(a-Azidobenzyl)penicillin | Generator | D-(-)-(Α-azidobenzyl)penicillin | Generator | Azidocillin, monopotassium salt, (2S-(2alpha,5alpha,6beta))-isomer | HMDB | Azidocillin, monosodium salt, (2S-(2alpha,5alpha,6beta(s*)))-isomer | HMDB | 6-(Azido-2-phenylacetamido)penicillanic acid | HMDB | Azidocillin, monopotassium salt, (2S-(2alpha,5alpha,6beta(r*)))-isomer | HMDB | Azidocillin, 2S-(2alpha,5alpha,6beta) | HMDB | Azidobenzylpenicillin | HMDB | Azidocillin, monopotassium salt, (2S-(2alpha,5alpha,6beta(s*)))-isomer | HMDB |
|
---|
Chemical Formula | C16H17N5O4S |
---|
Average Molecular Weight | 375.402 |
---|
Monoisotopic Molecular Weight | 375.100124747 |
---|
IUPAC Name | (2S,5R,6R)-6-[(2R)-2-azido-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
---|
Traditional Name | azidocillin |
---|
CAS Registry Number | 17243-38-8 |
---|
SMILES | [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N=[N+]=[N-])C1=CC=CC=C1)C(O)=O |
---|
InChI Identifier | InChI=1S/C16H17N5O4S/c1-16(2)11(15(24)25)21-13(23)10(14(21)26-16)18-12(22)9(19-20-17)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,22)(H,24,25)/t9-,10-,11+,14-/m1/s1 |
---|
InChI Key | ODFHGIPNGIAMDK-NJBDSQKTSA-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
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid or derivatives
- Phenylacetamide
- Monocyclic benzene moiety
- Benzenoid
- Thiazolidine
- Tertiary carboxylic acid amide
- Azetidine
- Secondary carboxylic acid amide
- Azo compound
- Azo imide
- Carboxamide group
- Dialkylthioether
- Azacycle
- Hemithioaminal
- Thioether
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Hydrocarbon derivative
- Organic oxygen compound
- Organonitrogen compound
- Carbonyl group
- Organic nitrogen compound
- Organooxygen compound
- Organopnictogen compound
- Organic oxide
- Aromatic heteropolycyclic compound
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | Not Available |
---|
Role | Not Available |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.61 g/L | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | | Show more...
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
Azidocillin,1TMS,isomer #1 | CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C | 2864.0 | Semi standard non polar | 33892256 | Azidocillin,1TMS,isomer #2 | CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O | 2851.2 | Semi standard non polar | 33892256 | Azidocillin,2TMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C | 2798.4 | Semi standard non polar | 33892256 | Azidocillin,2TMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C | 2846.9 | Standard non polar | 33892256 | Azidocillin,2TMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)[Si](C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C | 3949.1 | Standard polar | 33892256 | Azidocillin,1TBDMS,isomer #1 | CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 3089.0 | Semi standard non polar | 33892256 | Azidocillin,1TBDMS,isomer #2 | CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O | 3054.2 | Semi standard non polar | 33892256 | Azidocillin,2TBDMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 3193.3 | Semi standard non polar | 33892256 | Azidocillin,2TBDMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 3251.1 | Standard non polar | 33892256 | Azidocillin,2TBDMS,isomer #1 | CC1(C)S[C@@H]2[C@H](N(C(=O)[C@H](N=[N+]=[N-])C3=CC=CC=C3)[Si](C)(C)C(C)(C)C)C(=O)N2[C@H]1C(=O)O[Si](C)(C)C(C)(C)C | 4041.0 | Standard polar | 33892256 |
| Show more...
---|