Basic information
- Standard SMILES
CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O- InChIKey
NGHVIOIJCVXTGV-ALEPSDHESA-N- Molecular formula
- C8H12N2O3S
- Average molar mass
- 216.26 g/mol
- Monoisotopic mass
- 216.05686324
Overview
6-aminopenicillanic acid is a penicillanic acid compound having a (6R)-amino substituent. The active nucleus common to all penicillins, it may be substituted at the 6-amino position to form the semisynthetic penicillins, resulting in a variety of antibacterial and pharmacologic characteristics. It has a role as an allergen. It is functionally related to a penicillanic acid. It is a conjugate acid of a 6-aminopenicillanate. It is a tautomer of a 6-aminopenicillanic acid zwitterion.
Names & identifiers
- Preferred name
- 6-Aminopenicillanic acid
- IUPAC
- (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- English name
- 6-Aminopenicillanic acid
- Molecular formula
- C8H12N2O3S
- Molecular weight
- 216.26
Names & synonyms
6-Aminopenicillanic acid551-16-66-ApaPenicinPenin6-ApsAminopenicillanic acid(+)-6-Aminopenicillanic acid(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acidPhenacyl 6-aminopenicillinate6-Aminopenicillamine acid6-aminopenicillanate
Show more names
Amoxicillin EP Impurity AAMoxicillin Related CoMpound A6-amino penicillanic acid(6-APA)6-AminoFlucloxacillin EP Impurity C6-AMINO-2,2-DIMETHYL-5-OXOPERHYDROAZETO[2,1-B][1,3]THIAZOLE-3-CARBOXYLIC ACID6-AMINO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACIDAmoxicillin Related Compound A (15 mg) ((2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)
DTXSID7046097QR0C4R7XVNCHEBI:16705NSC-500716-amino-2,2-dimethylpenam-3alpha-carboxylic acid4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)-DTXCID5026097CHEBI:30938
Database identifiers
- CAS
551-16-6- PubChem CID
- 11082
- DTXSID
DTXSID7046097- ChEMBL
CHEMBL1236749- ChEBI
CHEBI:16705- UNII
- QR0C4R7XVN
- EC Number
- 208-993-4
- Nikkaji
- J14.224G
Properties
Computed structural properties
- XLogP
- -2.1
- Topological polar surface area
- 109 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 318
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Metabolite of Penicillin G, Penicillin V
Pharmaceuticals -> Antibiotics
Dissociation Constants2.3
Physicochemical properties
- Melting point
- 198 · 198-200 °C (dec.)(lit.)
- alpha
- 276.3 · 276.3 º (c=1.2, 0.1N HCl 22 ºC)
- Boiling point
- 460.2 · 460.2±45.0 °C(Predicted)
- Density
- 1.3418 · 1.3418 (rough estimate)
- refractive index
- 1.63 · 1.6300 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 2.46 g/l · 2.46g/l
- pka
- 2.3 · pKa 2.3 (Uncertain)
- form
- Fine Powder
- color
- White to cream
- PH
- 3.4 · 3.4 (100g/l, H2O)
- optical activity
- 22 · [α]22/D +276.3°, c = 1.2 in 0.1 M HCl
- Water Solubility
- Soluble in water and hydrochoric acid.
- Merck
- 14 · 14,458
- BRN
- 15080 · 15080
- Stability
- Light sensitive
- InChI
- 1S/C8H12N2O3S/c1-8(2)4(7(12)13)10-5(11)3(9)6(10)14-8/h3-4,6H,9H2,1-2H3,(H,12,13)/t3-,4+,6-/m1/s1
- InChIKey
- NGHVIOIJCVXTGV-SDKNWNMFSA-N
- SMILES
- CC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(O)=O
- LogP
- -3.87 at · -3.87 at 22.5℃
- CAS DataBase Reference
- 551 · 551-16-6(CAS DataBase Reference)
- FDA UNII
- 0 C4R7XVN · QR0C4R7XVN
- EPA Substance Registry System
- 6 · 6-Aminopenicillanic acid (551-16-6)
- UNSPSC Code
- 77101502 · 77101502
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 319 · H319
- Precautionary statements
- 264 · P264-P280-P305+P351+P338-P337+P313
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- Hazard Codes
- Xn
- Risk Statements
- 42 · 42/43
- Safety Statements
- 22 · 22-36/37-45-37-24-36
- WGK Germany
- 2 · 2
- RTECS
- 8225000 · XH8225000
- F
- 10 · 10
- TSCA
- TSCA listed
- HS Code
- 29349990 · 29349990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 · Eye Irrit. 2
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 79.4% (50 of 63) of all reports.
Danger
H317 (15.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 63 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationStatus: Active Update: 17-12-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/14138
Hazard Classes and CategoriesSkin Sens. 1 (15.9%)
Safety data
- F
- 10
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- XH8225000
- hs_code
- 29349990
- risk_code
- 42/43
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 22-36/37-45-37-24-36
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H319
- REACH Registrations
- Active
- Hazard Classifications
- Eye Irrit. 2
- Precautionary statements
- P264-P280-P305+P351+P338-P337+P313
Chemistry & industry
Pharmacology
Tissue LocationsKidney
Cellular LocationsCytoplasm
Uses & manufacturing
General Manufacturing Information4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)-: INACTIVE
Applications
Uses(+)-6-Aminopenicillanic Acid is the core structure in penicillins, obtained from the fermentation brew of the Penicillium mold. (+)-6-Aminopenicillanic Acid is used as the main starting block for the preparation of numerous semisynthetic penicillins.
Uses6-Aminopenicillanic acid is the basic unit in penicillins, which is obtained from the fermentation brew of the Penicillium mold. It acts as a starting material for the preparation of many semisynthetic penicillins. Further, it serves as apharmaceutical intermediate. In addition to this, it is used in antibiotics research and experimental application.
General DescriptionChemical structure: -lactam
Upstream & downstream products
Upstream raw materials
Downstream products
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国药集团化学试剂有限公司86-21-63210123 · [email protected]
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Additional notes
DefinitionChEBI: A penicillanic acid compound having a (6R)-amino substituent. The active nucleus common to all penicillins, it may be substituted at the 6-amino position to form the semisynthetic penicillins, resulting in a variety of antibacterial and ph rmacologic characteristics.
Related reactions
65 records
Linked notes
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