NP-MRD: Showing NP-Card for (5r,6r)-3-[(r)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (NP0226481)

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Record Information

Version

2.0

Created at

2022-09-06 05:31:57 UTC

Updated at

2022-09-06 05:31:57 UTC

NP-MRD ID

NP0226481

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5r,6r)-3-[(r)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Description

Carpetimycin C belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain. Based on a literature review very few articles have been published on Carpetimycin C.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062207312D          

 23 24  0  0  1  0            999 V2000
    4.4219   -1.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0094   -0.7986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1844   -0.7986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4219   -0.0842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0094    0.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1844    0.6303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7719    1.3448    0.0000 S   0  3  1  0  0  0  0  0  0  0  0  0
    3.1844    2.0593    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.9469    1.3448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4620    0.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7169   -0.1073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1649   -0.7204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5239   -0.2788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6773    0.9323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1477    0.9323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310    0.3489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1477    1.7573    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7310    2.3406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3144    2.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1477    2.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3144    1.7573    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6773    1.7573    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4620    2.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  4  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 14  1  1  0  0  0
 22 23  1  0  0  0  0
  9 23  1  0  0  0  0
M  CHG  2   7   1   8  -1
M  END
> <DATABASE_ID>
NP0226481

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)=NCC[S@@+]([O-])C1=C(N2[C@H](C1)[C@@H](C2=O)C(C)(C)O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H20N2O6S/c1-7(17)15-4-5-23(22)9-6-8-10(14(2,3)21)12(18)16(8)11(9)13(19)20/h8,10,21H,4-6H2,1-3H3,(H,15,17)(H,19,20)/t8-,10+,23-/m1/s1

> <INCHI_KEY>
SZSFOKCNKPUNLN-XJBZETAWSA-N

> <FORMULA>
C14H20N2O6S

> <MOLECULAR_WEIGHT>
344.38

> <EXACT_MASS>
344.104207546

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
34.80326340543665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,6R)-3-[(R)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

> <JCHEM_LOGP>
-4.462139679168806

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.9350276880057273

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.487840189625367

> <JCHEM_PKA_STRONGEST_BASIC>
5.967945581366621

> <JCHEM_POLAR_SURFACE_AREA>
127.50000000000001

> <JCHEM_REFRACTIVITY>
84.79670000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6R)-3-[(R)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       8.254  -2.824   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.484  -1.491   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.944  -1.491   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       8.254  -0.157   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.484   1.177   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.944   1.177   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       5.174   2.510   0.000  0.00  0.00           S+1
HETATM    8  O   UNK     0       5.944   3.844   0.000  0.00  0.00           O-1
HETATM    9  C   UNK     0       3.634   2.510   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.729   1.264   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.205  -0.200   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.174  -1.345   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.711  -0.520   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       1.264   1.740   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -0.276   1.740   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.365   0.651   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.276   3.280   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.365   4.369   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.454   5.458   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.276   5.458   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -2.454   3.280   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.264   3.280   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.729   3.756   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   23                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   22                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22   17   14   23                                                  
CONECT   23   22    9                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
3-(2-Acetamidoethylsulfinyl)-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo(3.2.0)hept-2-ene-2-carboxylic acid	MeSH

Chemical Formula

C₁₄H₂₀N₂O₆S

Average Mass

344.3800 Da

Monoisotopic Mass

344.10421 Da

IUPAC Name

(5R,6R)-3-[(R)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Traditional Name

(5R,6R)-3-[(R)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(O)=NCC[S@@+]([O-])C1=C(N2[C@H](C1)[C@@H](C2=O)C(C)(C)O)C(O)=O

InChI Identifier

InChI=1S/C14H20N2O6S/c1-7(17)15-4-5-23(22)9-6-8-10(14(2,3)21)12(18)16(8)11(9)13(19)20/h8,10,21H,4-6H2,1-3H3,(H,15,17)(H,19,20)/t8-,10+,23-/m1/s1

InChI Key

SZSFOKCNKPUNLN-XJBZETAWSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thienamycins. These are beta-lactam antibiotics that differ from penicillins in having the thiazolidine sulfur atom replaced by carbon, the sulfur then becoming the first atom in the side chain.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Thienamycins

Alternative Parents

Substituents

Thienamycin
Alpha-amino acid or derivatives
Pyrroline carboxylic acid
Pyrroline carboxylic acid or derivatives
Azepine
Acetamide
Pyrroline
Tertiary carboxylic acid amide
Tertiary alcohol
Azetidine
Carboxamide group
Sulfoxide
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Sulfinyl compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Organic oxide
Carbonyl group
Organooxygen compound
Organosulfur compound
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

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	-4.5	ChemAxon
pKa (Strongest Acidic)	2.49	ChemAxon
pKa (Strongest Basic)	5.97	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	127.5 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.8 m³·mol⁻¹	ChemAxon
Polarizability	34.8 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018517

Chemspider ID

34985093

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54333105

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5r,6r)-3-[(r)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (NP0226481)

MOL for NP0226481 ((5r,6r)-3-[(r)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

3D MOL for NP0226481 ((5r,6r)-3-[(r)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

3D SDF for NP0226481 ((5r,6r)-3-[(r)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

3D-SDF for NP0226481 ((5r,6r)-3-[(r)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

PDB for NP0226481 ((5r,6r)-3-[(r)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

3D PDB for NP0226481 ((5r,6r)-3-[(r)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

SMILES for NP0226481 ((5r,6r)-3-[(r)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

INCHI for NP0226481 ((5r,6r)-3-[(r)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

Structure for NP0226481 ((5r,6r)-3-[(r)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)

3D Structure for NP0226481 ((5r,6r)-3-[(r)-2-[(1-hydroxyethylidene)amino]ethanesulfinyl]-6-(2-hydroxypropan-2-yl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid)