NP-MRD: Showing NP-Card for 3-Mercaptolactate-cysteine disulfide (NP0087533)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-11 16:52:20 UTC

Updated at

2022-05-11 16:52:20 UTC

NP-MRD ID

NP0087533

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Mercaptolactate-cysteine disulfide

Description

3-Mercaptolactate-cysteine disulfide, also known as hcetc or S-(2-hydroxy-2-carboxyethylthio)cysteine, belongs to the class of organic compounds known as l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated. Addition of cysteine to the diet did increase the excretion of this disulfide (PMID: 3888441 , 527218 , 6945862 , 5644041 ). 3-Mercaptolactate-cysteine disulfide is a very strong basic compound (based on its pKa). 3-Mercaptolactate-cysteine disulfide was first documented in 1985 (PMID: 3888441). 3-Mercaptolactate-cysteine disulfide is a potentially toxic compound.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231220412D          

 14 13  0  0  1  0            999 V2000
   17.3510   -5.3996    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.3510   -6.2246    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.3510   -7.8747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4945   -4.1621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9220   -8.6997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7799   -2.9246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2075   -7.4622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.3510   -3.7496    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0655   -4.1621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   18.0655   -4.9871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6366   -7.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6366   -6.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7799   -3.7496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9220   -7.8747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 10  1  0  0  0  0
  2 12  1  0  0  0  0
  3 11  1  0  0  0  0
  4 13  1  0  0  0  0
  5 14  1  0  0  0  0
  6 13  2  0  0  0  0
  7 14  2  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0087533

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO5S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4,8H,1-2,7H2,(H,9,10)(H,11,12)/t3-,4?/m0/s1

> <INCHI_KEY>
MAFDYIDMXCXBRB-WUCPZUCCSA-N

> <FORMULA>
C6H11NO5S2

> <MOLECULAR_WEIGHT>
241.285

> <EXACT_MASS>
241.007863847

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
22.105696041289708

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}-2-hydroxypropanoic acid

> <ALOGPS_LOGP>
-3.08

> <JCHEM_LOGP>
-3.6464472116655497

> <ALOGPS_LOGS>
-0.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.560210797648136

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.6834861757602564

> <JCHEM_PKA_STRONGEST_BASIC>
9.040677528575356

> <JCHEM_POLAR_SURFACE_AREA>
120.84999999999998

> <JCHEM_REFRACTIVITY>
53.21430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.83e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hcetc

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      32.389 -10.079   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      32.389 -11.619   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0      32.389 -14.699   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      36.390  -7.769   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      29.721 -16.239   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      35.056  -5.459   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      28.387 -13.929   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      32.389  -6.999   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      33.722  -7.769   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      33.722  -9.309   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      31.055 -13.929   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.055 -12.389   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      35.056  -6.999   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.721 -14.699   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1   12                                                       
CONECT    3   11                                                            
CONECT    4   13                                                            
CONECT    5   14                                                            
CONECT    6   13                                                            
CONECT    7   14                                                            
CONECT    8    9                                                            
CONECT    9    8   10   13                                                  
CONECT   10    1    9                                                       
CONECT   11    3   12   14                                                  
CONECT   12    2   11                                                       
CONECT   13    4    6    9                                                  
CONECT   14    5    7   11                                                  
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
3-Mercaptolactate-cysteine disulphide	Generator
3-Mercaptolactic acid-cysteine disulfide	Generator
3-Mercaptolactic acid-cysteine disulphide	Generator
3-((2-Carboxy-2-hydroxyethyl)dithio)-L-alanine	HMDB
beta-Mercaptolactate cysteine disulfide	HMDB
Hcetc	HMDB
S-(2-Hydroxy-2-carboxyethylthio)cysteine	HMDB
3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}-2-hydroxypropanoate	HMDB
3-{[(2R)-2-amino-2-carboxyethyl]disulphanyl}-2-hydroxypropanoate	HMDB
3-{[(2R)-2-amino-2-carboxyethyl]disulphanyl}-2-hydroxypropanoic acid	HMDB
3-Mercaptolactate-cysteine disulfide	MeSH

Chemical Formula

C₆H₁₁NO₅S₂

Average Mass

241.2850 Da

Monoisotopic Mass

241.00786 Da

IUPAC Name

3-{[(2R)-2-amino-2-carboxyethyl]disulfanyl}-2-hydroxypropanoic acid

Traditional Name

hcetc

CAS Registry Number

Not Available

SMILES

N[C@@H](CSSCC(O)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C6H11NO5S2/c7-3(5(9)10)1-13-14-2-4(8)6(11)12/h3-4,8H,1-2,7H2,(H,9,10)(H,11,12)/t3-,4?/m0/s1

InChI Key

MAFDYIDMXCXBRB-WUCPZUCCSA-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 l-cysteine-s-conjugates. L-cysteine-S-conjugates are compounds containing L-cysteine where the thio-group is conjugated.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-cysteine-S-conjugates

Alternative Parents

Substituents

L-cysteine-s-conjugate
Alpha-amino acid
L-alpha-amino acid
Alpha-hydroxy acid
Dicarboxylic acid or derivatives
Hydroxy acid
Monosaccharide
Amino acid
Dialkyldisulfide
Organic disulfide
Secondary alcohol
Carboxylic acid
Sulfenyl compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Primary aliphatic amine
Organic oxide
Organopnictogen compound
Alcohol
Carbonyl group
Amine
Organic oxygen compound
Organic nitrogen compound
Organosulfur compound
Primary amine
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	-3.1	ALOGPS
logP	-3.6	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	1.68	ChemAxon
pKa (Strongest Basic)	9.04	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	120.85 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	53.21 m³·mol⁻¹	ChemAxon
Polarizability	22.11 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

HMDB0006512

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023951

KNApSAcK ID

Not Available

Chemspider ID

167948

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2742951

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

193536

PDB ID

Not Available

ChEBI ID

140723

Good Scents ID

Not Available

References

General References

Crawhall JC: A review of the clinical presentation and laboratory findings in two uncommon hereditary disorders of sulfur amino acid metabolism, beta-mercaptolactate cysteine disulfideuria and sulfite oxidase deficiency. Clin Biochem. 1985 Jun;18(3):139-42. doi: 10.1016/s0009-9120(85)80097-7. [PubMed:3888441 ]

Showing NP-Card for 3-Mercaptolactate-cysteine disulfide (NP0087533)

MOL for NP0087533 (3-Mercaptolactate-cysteine disulfide)

3D MOL for NP0087533 (3-Mercaptolactate-cysteine disulfide)

3D SDF for NP0087533 (3-Mercaptolactate-cysteine disulfide)

3D-SDF for NP0087533 (3-Mercaptolactate-cysteine disulfide)

PDB for NP0087533 (3-Mercaptolactate-cysteine disulfide)

3D PDB for NP0087533 (3-Mercaptolactate-cysteine disulfide)

SMILES for NP0087533 (3-Mercaptolactate-cysteine disulfide)

INCHI for NP0087533 (3-Mercaptolactate-cysteine disulfide)

Structure for NP0087533 (3-Mercaptolactate-cysteine disulfide)

3D Structure for NP0087533 (3-Mercaptolactate-cysteine disulfide)