NP-MRD: Showing NP-Card for (2s,5r,6r)-6-[(1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (NP0159297)

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Record Information

Version

2.0

Created at

2022-09-02 17:01:48 UTC

Updated at

2022-09-02 17:01:48 UTC

NP-MRD ID

NP0159297

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,5r,6r)-6-[(1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Description

Penicillin G, also known as benzylpenicilline or PCG, belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. Penicillin G is a drug which is used for use in the treatment of severe infections caused by penicillin g-susceptible microorganisms when rapid and high penicillin levels are required such as in the treatment of septicemia, meningitis, pericarditis, endocarditis and severe pneumonia. A penicillin in which the substituent at position 6 of the penam ring is a phenylacetamido group. (2s,5r,6r)-6-[(1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is found in Sarocladium strictum, Penicillium chrysogenum and Streptomyces clavuligerus. (2s,5r,6r)-6-[(1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid was first documented in 2002 (PMID: 11906332). Penicillin G is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 43  0  0  0  0  0  0  0  0999 V2000
   -3.2688    1.0360    3.1916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3923    0.6697    2.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5051    1.8395    1.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3964   -0.8184    2.3456 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7850   -1.6980    0.7810 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6402   -1.8770   -0.1531 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6106   -1.2932    0.1658 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7800   -1.6948   -0.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7518   -2.5605   -1.4384 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1229   -1.1158   -0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5739   -0.1227   -1.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4169    1.2515   -0.9347 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8065    2.2076   -1.8383 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3790    1.8488   -3.0459 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5410    0.4978   -3.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1409   -0.4554   -2.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4407   -1.0069   -1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4726   -0.7177   -2.3015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2657   -0.5392    0.0102 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1804    0.2383    0.8125 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3872   -0.5230    1.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3172   -0.0783    1.8432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6133   -1.7761    0.5459 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6351    0.1667    3.7680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7108    1.7501    3.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1279    1.6599    2.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568    1.4763    1.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6643    2.6743    2.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8406    2.1887    0.6368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4785   -2.5192    0.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5309   -2.8730   -0.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6889   -0.5671    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8879   -1.9430   -0.2159 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1787   -0.7057    0.8166 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9701    1.5515    0.0122 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6720    3.2622   -1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6888    2.5768   -3.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9784    0.1450   -4.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2916   -1.5143   -2.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4064    1.1754    0.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9639   -1.8168   -0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  1  0
  2 20  1  0
 20 19  1  0
 19 17  1  0
 17 18  2  0
 17  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 20 21  1  0
 21 23  1  0
 21 22  2  0
 19  5  1  0
 16 11  1  0
  6  5  1  0
  5 30  1  1
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
 20 40  1  6
  6 31  1  6
  7 32  1  0
 10 33  1  0
 10 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 23 41  1  0
M  END

1053
  Mrv0541 02231215122D          

 24 26  0  0  1  0            999 V2000
    7.6201    1.0703    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215   -0.5975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3230   -1.6623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6819   -1.2207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4089    0.3950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8354   -0.0096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4215    1.4034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8354    0.8154    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.1049    0.4029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6201   -0.2646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.0036    0.8188    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.0036   -0.0130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7724   -0.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7724    0.8878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8750   -1.0491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6241    1.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0420    1.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2446    1.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0295    0.7677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6625    2.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2322    0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8651    1.9368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.1404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7335    1.4675    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1  9  1  0  0  0  0
  2 12  2  0  0  0  0
  3 15  1  0  0  0  0
  4 15  2  0  0  0  0
  5 16  2  0  0  0  0
  6  8  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  1  0  0  0  0
 11  7  1  1  0  0  0
  7 16  1  0  0  0  0
  8 11  1  0  0  0  0
  8 24  1  6  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  6  0  0  0
 11 12  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  2  0  0  0  0
 21 23  2  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159297

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1

> <INCHI_KEY>
JGSARLDLIJGVTE-MBNYWOFBSA-N

> <FORMULA>
C16H18N2O4S

> <MOLECULAR_WEIGHT>
334.39

> <EXACT_MASS>
334.098727764

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
33.541594084546915

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
1.0806779529999997

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.119397282151533

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5292810836901047

> <JCHEM_PKA_STRONGEST_BASIC>
-2.634074595453018

> <JCHEM_POLAR_SURFACE_AREA>
86.71

> <JCHEM_REFRACTIVITY>
84.52780000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
penicillin G

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1053                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      14.224   1.998   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0      10.120  -1.115   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.670  -3.103   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      16.206  -2.279   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       8.230   0.737   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      12.759  -0.018   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      10.120   2.620   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      12.759   1.522   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      15.129   0.752   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.224  -0.494   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.207   1.528   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.207  -0.024   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.375  -0.153   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.375   1.657   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.700  -1.958   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.632   2.224   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.545   3.315   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.057   2.920   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.655   1.433   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.970   4.011   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.167   1.037   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.482   3.615   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.080   2.129   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0      12.569   2.739   0.000  0.00  0.00           H+0
CONECT    1    8    9                                                       
CONECT    2   12                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5   16                                                            
CONECT    6    8   10   12                                                  
CONECT    7   11   16                                                       
CONECT    8    1    6   11   24                                             
CONECT    9    1   10   13   14                                             
CONECT   10    6    9   15                                                  
CONECT   11    7    8   12                                                  
CONECT   12    2    6   11                                                  
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15    3    4   10                                                  
CONECT   16    5    7   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   23                                                       
CONECT   22   20   23                                                       
CONECT   23   21   22                                                       
CONECT   24    8                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
6-(2-Phenylacetamido)penicillanic acid	ChEBI
Bencilpenicilina	ChEBI
Bensylpenicillin	ChEBI
Benzyl benicillin	ChEBI
Benzylpenicilline	ChEBI
Benzylpenicillinic acid	ChEBI
Benzylpenicillinum	ChEBI
Free penicillin II	ChEBI
PCG	ChEBI
PG	ChEBI
Benzylpenicillin	Kegg
(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
6-(2-Phenylacetamido)penicillanate	Generator
Benzylpenicillinate	Generator
Antibioticos brand OF penicillin g sodium	HMDB
Britannia brand OF penicillin g sodium	HMDB
Or-pen	HMDB
Pekamin	HMDB
Penibiot	HMDB
Pfizerpen	HMDB
Sodipen	HMDB
Van-pen-g	HMDB
Benzylpenicillin potassium	HMDB
CEPA brand OF penicillin g sodium	HMDB
Grünenthal brand OF penicillin g potassium	HMDB
Jenapharm brand OF penicillin g sodium	HMDB
Llorente brand OF penicillin g sodium	HMDB
Medical brand OF penicillin g sodium	HMDB
Normon brand OF penicillin g sodium	HMDB
Penicillin grünenthal	HMDB
Sodium penicillin	HMDB
Ursopen	HMDB
Benpen	HMDB
Coliriocilina	HMDB
Ern brand OF penicillin g sodium	HMDB
Lakeside brand OF penicillin g sodium	HMDB
Medical brand OF penicillin g potassium	HMDB
Ortega brand OF penicillin g potassium	HMDB
Penicilina g llorente	HMDB
Penicillin g potassium	HMDB
Penilevel	HMDB
Peniroger	HMDB
Pfizer brand OF penicillin g potassium	HMDB
Sodiopen	HMDB
Sodium benzylpenicillin	HMDB
UCB brand OF penicillin g sodium	HMDB
Unicilina	HMDB
Bioniche brand OF penicillin g sodium	HMDB
CSL Brand OF penicillin g sodium	HMDB
Clonmel brand OF penicillin g sodium	HMDB
Crystapen	HMDB
Parcillin	HMDB
Parmed brand OF penicillin g potassium	HMDB
Pengesod	HMDB
Penicillin g jenapharm	HMDB
Penicillin g sodium	HMDB
Vangard brand OF penicillin g potassium	HMDB
Penicillin g	ChEBI

Chemical Formula

C₁₆H₁₈N₂O₄S

Average Mass

334.3900 Da

Monoisotopic Mass

334.09873 Da

IUPAC Name

(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

penicillin G

CAS Registry Number

Not Available

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C16H18N2O4S/c1-16(2)12(15(21)22)18-13(20)11(14(18)23-16)17-10(19)8-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1

InChI Key

JGSARLDLIJGVTE-MBNYWOFBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Acremonium strictum	LOTUS Database	35616633
Penicillium chrysogenum	LOTUS Database	35616633
Streptomyces clavuligerus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Dipeptides

Alternative Parents

Substituents

Alpha-dipeptide
Penicillin
N-acyl-alpha amino acid or derivatives
Alpha-amino acid or derivatives
Phenylacetamide
Penam
Monocyclic benzene moiety
Benzenoid
Beta-lactam
Thiazolidine
Tertiary carboxylic acid amide
Azetidine
Carboxamide group
Lactam
Secondary carboxylic acid amide
Carboxylic acid
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Dialkylthioether
Hemithioaminal
Thioether
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

penicillin (CHEBI:18208 )
penams (C05551 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.92	ALOGPS
logP	1.08	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	3.53	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.71 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	84.53 m³·mol⁻¹	ChemAxon
Polarizability	33.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0015186

DrugBank ID

DB01053

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5693

KEGG Compound ID

C05551

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzylpenicillin

METLIN ID

Not Available

PubChem Compound

5904

PDB ID

PNN

ChEBI ID

18208

Good Scents ID

Not Available

References

General References

Akesson A, Ingvarsson S, Karlsson F, Leyva L, Blanca M, Cuerden SA, Smith JA, Coleman JW, Borrebaeck CA: Characterization of specific IgE response in vitro against protein and drug allergens using atopic and normal donors. Allergy. 2002 Mar;57(3):193-200. doi: 10.1034/j.1398-9995.2002.1o3321.x. [PubMed:11906332 ]
LOTUS database [Link]

Showing NP-Card for (2s,5r,6r)-6-[(1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (NP0159297)

MOL for NP0159297 ((2s,5r,6r)-6-[(1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D MOL for NP0159297 ((2s,5r,6r)-6-[(1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D SDF for NP0159297 ((2s,5r,6r)-6-[(1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D-SDF for NP0159297 ((2s,5r,6r)-6-[(1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

PDB for NP0159297 ((2s,5r,6r)-6-[(1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D PDB for NP0159297 ((2s,5r,6r)-6-[(1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

SMILES for NP0159297 ((2s,5r,6r)-6-[(1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

INCHI for NP0159297 ((2s,5r,6r)-6-[(1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

Structure for NP0159297 ((2s,5r,6r)-6-[(1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D Structure for NP0159297 ((2s,5r,6r)-6-[(1-hydroxy-2-phenylethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)