NP-MRD: Showing NP-Card for 3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (NP0150765)

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Record Information

Version

2.0

Created at

2022-09-02 06:58:32 UTC

Updated at

2022-09-02 06:58:32 UTC

NP-MRD ID

NP0150765

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Description

3-[(2-Aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]Heptane-2-carboxylic acid, also known as carbapenem biosynthesis intermediate 5, belongs to the class of organic compounds known as carbapenams. These are beta-lactams with a saturated carbapenem skeleton. 3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid is found in Apis cerana. 3-[(2-Aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]Heptane-2-carboxylic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.9768   -0.1038    0.8836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7068    0.7202   -0.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2473    1.1135   -0.4533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6272    1.2819    0.9132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9780    2.0572    1.8526 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6369    0.3176    0.6699 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5054   -0.5592    0.6717 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0975   -1.7470    1.5161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0298   -1.8388    2.0558 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0490   -2.7604    1.6736 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7536   -0.9651   -0.7328 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3596   -0.8975   -1.4014 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2293    0.6209   -1.4920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5835    1.2093   -0.1466 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4063    0.3367    0.6614 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3027   -0.1797   -1.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3865   -0.0886   -0.5104 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5797    0.3598    1.7971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0871   -0.2593    0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5503   -1.1237    0.7953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0106    0.0574   -1.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3699    1.5994   -0.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0288    1.9462   -1.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -0.1402    1.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6207   -2.9734    0.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3841   -2.0376   -0.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1909    0.4579   -2.0623 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7299    1.4384   -2.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2281    2.1155   -0.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7146    1.6084    0.4085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8163   -0.4549    0.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8172   -0.1192    1.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1752    0.7929   -1.7561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6192   -0.7185   -2.4272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8922   -1.0663   -0.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 17  1  0
 17 16  1  0
 16 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 11  7  1  0
  7  6  1  0
  6  4  1  0
  4  5  2  0
  7  8  1  0
  8 10  1  0
  8  9  2  0
  4  3  1  0
  6 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  2 22  1  0
  3 23  1  6
 17 35  1  1
 16 33  1  0
 16 34  1  0
 11 26  1  1
 13 27  1  0
 13 28  1  0
 14 29  1  0
 14 30  1  0
 15 31  1  0
 15 32  1  0
  7 24  1  1
 10 25  1  0
M  END


  Mrv1652306232023102D          

 17 18  0  0  0  0            999 V2000
   -0.9843    0.2050    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9843    1.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1982   -0.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8151    0.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8151    1.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2017    1.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2845    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0602   -0.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4082   -0.3844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5357    1.4463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1117    0.6188    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8670   -1.0016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912   -1.4463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2494    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8221    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5358    0.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2494    1.0359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  1  0  0  0  0
  8 13  2  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  4  5  1  0  0  0  0
  6  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0150765

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1C2CC(SCCN)C(N2C1=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H18N2O3S/c1-2-6-7-5-8(17-4-3-12)9(11(15)16)13(7)10(6)14/h6-9H,2-5,12H2,1H3,(H,15,16)

> <INCHI_KEY>
OJZAYZYCCIMRRC-UHFFFAOYSA-N

> <FORMULA>
C11H18N2O3S

> <MOLECULAR_WEIGHT>
258.34

> <EXACT_MASS>
258.103813622

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.32612029229631

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

> <ALOGPS_LOGP>
-0.16

> <JCHEM_LOGP>
-2.5127398149685822

> <ALOGPS_LOGS>
-1.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6766439591108893

> <JCHEM_PKA_STRONGEST_BASIC>
9.708737999044903

> <JCHEM_POLAR_SURFACE_AREA>
83.63000000000001

> <JCHEM_REFRACTIVITY>
64.89290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.47e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JUN-20         0                                  
HETATM    1  N   UNK     0      -1.837   0.383   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.837   1.921   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.370  -0.087   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.388   0.370   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.388   1.921   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.376   2.391   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.531   1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.112  -1.554   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.495  -0.718   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.733   2.700   0.000  0.00  0.00           C+0
HETATM   11  S   UNK     0       2.075   1.155   0.000  0.00  0.00           S+0
HETATM   12  O   UNK     0       1.618  -1.870   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.917  -2.700   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -6.066   1.927   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.401   1.927   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.733   1.168   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       6.066   1.934   0.000  0.00  0.00           N+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9    5                                                  
CONECT    5    2   10    4                                                  
CONECT    6    2    7                                                       
CONECT    7    3   11    6                                                  
CONECT    8    3   12   13                                                  
CONECT    9    4                                                            
CONECT   10    5   14                                                       
CONECT   11    7   15                                                       
CONECT   12    8                                                            
CONECT   13    8                                                            
CONECT   14   10                                                            
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
3-(2-Aminoethylthio)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	ChEBI
Carbapenem biosynthesis intermediate 5	ChEBI
3-(2-Aminoethylthio)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
Carbapenem biosynthesis intermediic acid 5	Generator
3-[(2-Aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
3-[(2-Aminoethyl)sulphanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate	Generator
3-[(2-Aminoethyl)sulphanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid	Generator

Chemical Formula

C₁₁H₁₈N₂O₃S

Average Mass

258.3400 Da

Monoisotopic Mass

258.10381 Da

IUPAC Name

3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

Traditional Name

3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

CCC1C2CC(SCCN)C(N2C1=O)C(O)=O

InChI Identifier

InChI=1S/C11H18N2O3S/c1-2-6-7-5-8(17-4-3-12)9(11(15)16)13(7)10(6)14/h6-9H,2-5,12H2,1H3,(H,15,16)

InChI Key

OJZAYZYCCIMRRC-UHFFFAOYSA-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
Apis cerana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbapenams. These are beta-lactams with a saturated carbapenem skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactams

Sub Class

Beta lactams

Direct Parent

Carbapenams

Alternative Parents

Substituents

Carbapenam
Alpha-amino acid or derivatives
Caprolactam
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Azepane
Tertiary carboxylic acid amide
Pyrrolidine
Amino acid or derivatives
Amino acid
Azetidine
Carboxamide group
Thioether
Sulfenyl compound
Dialkylthioether
Azacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Primary aliphatic amine
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Carbonyl group
Primary amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Amine
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	-0.16	ALOGPS
logP	-2.5	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	9.71	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.63 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	64.89 m³·mol⁻¹	ChemAxon
Polarizability	27.33 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

Not Available

Chemspider ID

58827213

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92042762

PDB ID

Not Available

ChEBI ID

132289

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid (NP0150765)

MOL for NP0150765 (3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D MOL for NP0150765 (3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D SDF for NP0150765 (3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D-SDF for NP0150765 (3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

PDB for NP0150765 (3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D PDB for NP0150765 (3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

SMILES for NP0150765 (3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

INCHI for NP0150765 (3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

Structure for NP0150765 (3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)

3D Structure for NP0150765 (3-[(2-aminoethyl)sulfanyl]-6-ethyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylic acid)