6-Aminopenicillanic acid

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for 6-Aminopenicillanic acid are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the 6-Aminopenicillanic acid?

The molecule 6-Aminopenicillanic acid presents a molecular formula of C8H12N2O3S and its IUPAC name is (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid.

6-Aminopenicillanic acid is a molecule with the molecular formula C7H8N2O2. It is a white solid that is insoluble in water. It is a derivative of penicillin..

6-Aminopenicillanic acid is used in the synthesis of penicillins and cephalosporins. It is also used as a reagent in the determination of p-aminophenol..

6-Aminopenicillanic acid is a white solid that is insoluble in water. It has a molecular weight of 144.15 g/mol and a melting point of 165-167 °C..

3D structure

Cartesian coordinates

Geometry of 6-Aminopenicillanic acid in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

6-Aminopenicillanic acid NGHVIOIJCVXTGV-ALEPSDHESA-N chemical compound 2D structure molecule svg
6-Aminopenicillanic acid

 

Molecule descriptors

 
IUPAC name(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
InChI codeInChI=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
InChI KeyNGHVIOIJCVXTGV-ALEPSDHESA-N
SMILESCC1(C)S[C@@H]2[C@H](N)C(=O)N2[C@H]1C(=O)O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (+)-6-Aminopenicillanic acid
  • (2S)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (2S,5R,6R)-(+)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (2S,5R,6R)-6-AMINO-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
  • (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptan-2-carbonsaeure
  • (2S,5R,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid (6-Aminopenicillanic Acid)
  • (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid
  • (3S, 5R, 6R)-6-amino-2,2-dimethylpenam-3-carboxylic acid
  • (3S,5R,6R)-6-amino-2,2-dimethylpenam-3-carboxylic acid
  • 09070_FLUKA
  • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
  • 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
  • 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-amino-3,3-dimethyl-7-oxo-, (2S,6R)-
  • 551-16-6
  • 6-Aminopenicillamine acid
  • 6-Aminopenicillanic acid
  • 6-Aminopenicillanicacid
  • 6-Apa
  • 6-Aps
  • 6-amino-2,2-dimethylpenam-3alpha-carboxylic acid
  • 6-amino-penicillanic acid
  • 6-aminopenici llanic acid
  • 6-aminopenicillanate
  • 6-aminopenicillanic-acid
  • 6-aminopenicillinic acid (6-APA)
  • 6beta-amino-2,2-dimethylpenam-3alpha-carboxylic acid
  • 6beta-aminopenicillanic acid
  • A0800
  • A830497
  • AC-11282
  • AI3-52557
  • Aminopenicillanic acid
  • Amoxicillin Related Compound A
  • BCP13375
  • BDBM50420257
  • C02954
  • CCG-50809
  • CS-W014265
  • DSSTox_CID_26097
  • DSSTox_GSID_46097
  • DSSTox_RID_81336
  • EC 208-993-4
  • Epitope ID:117703
  • HY-W013549
  • KS-5277
  • MFCD00005176
  • NCGC00160198-01
  • NSC 50071
  • NSC-50071
  • Penicin
  • Penin
  • Phenacyl 6-aminopenicillinate
  • Q2823234
  • QR0C4R7XVN
  • SR-01000640154-1
  • STR03060
  • W-105586
  • X1E
  • Z1741972222
  • [2S-(2alpha,5alpha,6beta)]-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • amino penicillanic acid
  • bmse000312
  • rel-(2R,6S)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • s12351
  • s5035

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3860188
  • CAS-551-16-6
  • UNII-QR0C4R7XVN
  • AKOS015907713
  • DTXSID7046097
  • CHEMBL1236749
  • CHEBI:16705
  • Tox21_111749
  • EINECS 208-993-4
  • SCHEMBL66332

Physico-Chemical properties

IUPAC name(2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Molecular formulaC8H12N2O3S
Molecular weight216.257
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity55.46
LogP0.1
Topological polar surface area108.9

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.