NP-MRD: Showing NP-Card for N-Acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine (NP0086902)

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Record Information

Version

2.0

Created at

2022-05-11 16:34:12 UTC

Updated at

2022-05-11 16:34:12 UTC

NP-MRD ID

NP0086902

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine

Description

N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine, also known as (R)-4-(2-acetamido-2-carboxyethylthio)-2-oxobutanoate or nac-OCPC, belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. N-Acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine was first documented in 1995 (PMID: 8750604). N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 29  0  0  0  0  0  0  0  0999 V2000
   -3.3577    2.5813    2.0248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9753    1.4576    1.1408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9394    0.8502    0.5687 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6435    1.0676    0.9306 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3543   -0.0832    0.0173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5647    0.5173   -1.0904 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0041   -0.4473   -2.4153 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.3013   -1.5917   -2.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6728   -0.9962   -2.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7903   -0.1830   -0.7876 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8656    1.0672   -0.9295 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8220   -0.7638    0.5558 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7467   -2.0149    0.7026 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9347    0.0617    1.6621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7063   -1.0746    0.8714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3404   -0.8175    2.0750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4603   -2.3430    0.4290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6851    2.5817    2.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1670    3.5352    1.4958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3972    2.5087    2.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8638    1.5551    1.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3376   -0.4408   -0.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2611    1.3331   -1.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2344    1.1678   -0.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1896   -2.4059   -1.4893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3765   -2.1888   -3.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3768   -1.8690   -1.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0066   -0.4296   -2.9028 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8268    0.4925    1.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0862   -3.1277    0.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 14  1  0
 12 13  2  0
  5 15  1  0
 15 17  1  0
 15 16  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  6
  6 23  1  0
  6 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 14 29  1  0
 17 30  1  0
M  END

2-Methylbutyryl CoA.mol
  Mrv0541 02231219252D          

 17 16  0  0  0  0            999 V2000
    2.1434    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.4125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  1  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  6  2  0  0  0  0
  1  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  2  0  0  0  0
  5  8  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
  2 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086902

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)N[C@@H](CSCCC(=O)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H13NO6S/c1-5(11)10-6(8(13)14)4-17-3-2-7(12)9(15)16/h6H,2-4H2,1H3,(H,10,11)(H,13,14)(H,15,16)/t6-/m0/s1

> <INCHI_KEY>
AHFWWWFNCBRMIV-LURJTMIESA-N

> <FORMULA>
C9H13NO6S

> <MOLECULAR_WEIGHT>
263.268

> <EXACT_MASS>
263.046357843

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
24.811188577232805

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{[(2R)-2-carboxy-2-acetamidoethyl]sulfanyl}-2-oxobutanoic acid

> <ALOGPS_LOGP>
-0.23

> <JCHEM_LOGP>
-0.4238657843333333

> <ALOGPS_LOGS>
-2.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.6571309871466933

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.733182860027261

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4948381328586549

> <JCHEM_POLAR_SURFACE_AREA>
120.77000000000001

> <JCHEM_REFRACTIVITY>
58.49760000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[(2R)-2-carboxy-2-acetamidoethyl]sulfanyl}-2-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 2-Methylbutyryl CoA.mol                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       4.001   1.540   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       2.667  -0.770   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.667   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   1.540   0.000  0.00  0.00           C+0
HETATM    5  S   UNK     0       0.000   0.770   0.000  0.00  0.00           S+0
HETATM    6  O   UNK     0       4.001   3.080   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.335   0.770   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  -1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.001  -3.080   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -5.335  -0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.667   0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.001  -3.080   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.335  -0.770   0.000  0.00  0.00           C+0
CONECT    1    3    6    7                                                  
CONECT    2    3   15                                                       
CONECT    3    2    1    4                                                  
CONECT    4    3    5                                                       
CONECT    5    4    8                                                       
CONECT    6    1                                                            
CONECT    7    1                                                            
CONECT    8    9    5                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   12   13   10                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10                                                            
CONECT   15   16   17    2                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Value	Source
(R)-4-(2-Acetamido-2-carboxyethylthio)-2-oxobutanoate	HMDB
(R)-4-(2-Acetamido-2-carboxyethylthio)-2-oxobutanoic acid	HMDB
NAc-OCPC	HMDB
4-{[(2R)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulfanyl}-2-oxobutanoate	HMDB
4-{[(2R)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulphanyl}-2-oxobutanoate	HMDB
4-{[(2R)-2-carboxy-2-[(1-hydroxyethylidene)amino]ethyl]sulphanyl}-2-oxobutanoic acid	HMDB
N-Acetyl-S-(3-oxo-3-carboxy-N-propyl)cysteine	MeSH

Chemical Formula

C₉H₁₃NO₆S

Average Mass

263.2680 Da

Monoisotopic Mass

263.04636 Da

IUPAC Name

4-{[(2R)-2-carboxy-2-acetamidoethyl]sulfanyl}-2-oxobutanoic acid

Traditional Name

4-{[(2R)-2-carboxy-2-acetamidoethyl]sulfanyl}-2-oxobutanoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@@H](CSCCC(=O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C9H13NO6S/c1-5(11)10-6(8(13)14)4-17-3-2-7(12)9(15)16/h6H,2-4H2,1H3,(H,10,11)(H,13,14)(H,15,16)/t6-/m0/s1

InChI Key

AHFWWWFNCBRMIV-LURJTMIESA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-L-alpha-amino acids

Alternative Parents

Substituents

N-acyl-l-alpha-amino acid
Cysteine or derivatives
Short-chain keto acid
Thia fatty acid
Alpha-keto acid
Dicarboxylic acid or derivatives
Keto acid
Fatty acyl
Acetamide
Alpha-hydroxy ketone
Carboxamide group
Secondary carboxylic acid amide
Ketone
Dialkylthioether
Sulfenyl compound
Thioether
Carboxylic acid
Organic oxide
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Organic nitrogen compound
Organic oxygen compound
Carbonyl group
Organopnictogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-0.23	ALOGPS
logP	-0.42	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	2.73	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	120.77 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	58.5 m³·mol⁻¹	ChemAxon
Polarizability	24.81 Å³	ChemAxon
Number of Rings	0	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

HMDB0002194

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022896

KNApSAcK ID

Not Available

Chemspider ID

13628313

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6537

PubChem Compound

20849151

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang J, Masuoka N, Ubuka T, Sugahara K, Kodama H: Identification of N-acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine in the urine of a patient with cystathioninuria using LC/APCI-MS. J Inherit Metab Dis. 1995;18(6):675-81. doi: 10.1007/BF02436756. [PubMed:8750604 ]

Showing NP-Card for N-Acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine (NP0086902)

MOL for NP0086902 (N-Acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

3D MOL for NP0086902 (N-Acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

3D SDF for NP0086902 (N-Acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

3D-SDF for NP0086902 (N-Acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

PDB for NP0086902 (N-Acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

3D PDB for NP0086902 (N-Acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

SMILES for NP0086902 (N-Acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

INCHI for NP0086902 (N-Acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

Structure for NP0086902 (N-Acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)

3D Structure for NP0086902 (N-Acetyl-S-(3-oxo-3-carboxy-n-propyl)cysteine)