NP-MRD: Showing NP-Card for L-Cysteic acid (NP0002718)

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Record Information

Version

2.0

Created at

2020-11-23 19:38:41 UTC

Updated at

2021-08-19 23:59:17 UTC

NP-MRD ID

NP0002718

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-Cysteic acid

Provided By

BMRB

Description

(R)-cysteate, also known as L-cysteic acid or 3-sulfoalanine, belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom (R)-cysteate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. L-Cysteic acid is found in Apis cerana, Claviceps purpurea, Pseudotsuga menziesii and Puccinia graminis. L-Cysteic acid was first documented in 1996 (PMID: 8981569). Based on a literature review a small amount of articles have been published on (R)-cysteate (PMID: 11750815) (PMID: 21719707).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


     RDKit          2D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -2.1561   -1.2224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7453   -0.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6655   -0.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0763    0.3064    0.0000 S   0  0  0  0  0  6  0  0  0  0  0  0
    1.5667    1.7172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5859   -1.1044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4871    0.8159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2549    0.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4348    1.9540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7314    0.9621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4202   -2.6989    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3028   -0.2554    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2357   -2.1236    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1751   -1.6140    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3317    1.2592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6338   -0.1511    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410    2.3729    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  2  0
  4  7  1  6
  2  8  1  0
  8  9  2  0
  8 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  1
  3 14  1  6
  3 15  1  0
  7 16  1  0
 10 17  1  0
M  END
> <DATABASE_ID>
NP0002718

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1

> <INCHI_KEY>
XVOYSCVBGLVSOL-REOHCLBHSA-N

> <FORMULA>
C3H7NO5S

> <MOLECULAR_WEIGHT>
169.156

> <EXACT_MASS>
169.004493029

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.484439770119895

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-amino-3-sulfopropanoic acid

> <ALOGPS_LOGP>
-2.39

> <JCHEM_LOGP>
-2.957299196822919

> <ALOGPS_LOGS>
-0.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
1.2422625178335887

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.7161956659222701

> <JCHEM_PKA_STRONGEST_BASIC>
8.793320902393107

> <JCHEM_POLAR_SURFACE_AREA>
117.69

> <JCHEM_REFRACTIVITY>
30.435000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.36e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cysteinesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

View in JSmol

Synonyms

Value	Source
(2R)-2-Amino-3-sulfopropanoic acid	ChEBI
2-Amino-3-sulfopropionic acid	ChEBI
3-SulfO-L-alanine	ChEBI
3-Sulfoalanine	ChEBI
CYSTEINEsulfonIC ACID	ChEBI
L-Cysteate	ChEBI
L-Cysteic acid	Kegg
(2R)-2-Amino-3-sulfopropanoate	Generator
(2R)-2-Amino-3-sulphopropanoate	Generator
(2R)-2-Amino-3-sulphopropanoic acid	Generator
2-Amino-3-sulfopropionate	Generator
2-Amino-3-sulphopropionate	Generator
2-Amino-3-sulphopropionic acid	Generator
3-SulphO-L-alanine	Generator
3-Sulphoalanine	Generator
CYSTEINEsulfonate	Generator
CYSTEINEsulphonate	Generator
CYSTEINEsulphonic acid	Generator
(R)-Cysteic acid	Generator
L-3-Sulfoalanine	HMDB
Cysteic acid	HMDB
2-Amino-3-sulfopropanoic acid	HMDB
Cysteate	HMDB
DL-Cysteic acid	HMDB

Chemical Formula

C₃H₇NO₅S

Average Mass

169.1560 Da

Monoisotopic Mass

169.00449 Da

IUPAC Name

(2R)-2-amino-3-sulfopropanoic acid

Traditional Name

cysteinesulfonic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C3H7NO5S/c4-2(3(5)6)1-10(7,8)9/h2H,1,4H2,(H,5,6)(H,7,8,9)/t2-/m0/s1

InChI Key

XVOYSCVBGLVSOL-REOHCLBHSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Apis cerana	LOTUS Database	35616633
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
Claviceps purpurea	LOTUS Database	35616633
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
Pseudotsuga menziesii	LOTUS Database	35616633
Puccinia graminis	LOTUS Database	35616633
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-alpha-amino acids. These are 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

L-alpha-amino acids

Alternative Parents

Not Available

Substituents

Not Available

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	1000000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.4	ALOGPS
logP	-3	ChemAxon
logS	-0.36	ALOGPS
pKa (Strongest Acidic)	-1.7	ChemAxon
pKa (Strongest Basic)	8.79	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	30.44 m³·mol⁻¹	ChemAxon
Polarizability	13.48 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

HMDB0303991

DrugBank ID

DB03661

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030145

KNApSAcK ID

Not Available

Chemspider ID

65718

KEGG Compound ID

C00506

BioCyc ID

L-CYSTEATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72886

PDB ID

Not Available

ChEBI ID

17285

Good Scents ID

rw1724871

References

General References

Eichhorn E, Leisinger T: Escherichia coli utilizes methanesulfonate and L-cysteate as sole sulfur sources for growth. FEMS Microbiol Lett. 2001 Dec 18;205(2):271-5. doi: 10.1111/j.1574-6968.2001.tb10960.x. [PubMed:11750815 ]
Sasahara A, Nanatani K, Enomoto M, Kuwahara S, Abe K: Substrate specificity of the aspartate:alanine antiporter (AspT) of Tetragenococcus halophilus in reconstituted liposomes. J Biol Chem. 2011 Aug 19;286(33):29044-29052. doi: 10.1074/jbc.M111.260224. Epub 2011 Jun 30. [PubMed:21719707 ]
Thompson GA, Kilpatrick IC: The neurotransmitter candidature of sulphur-containing excitatory amino acids in the mammalian central nervous system. Pharmacol Ther. 1996;72(1):25-36. doi: 10.1016/s0163-7258(96)00097-6. [PubMed:8981569 ]

Showing NP-Card for L-Cysteic acid (NP0002718)

MOL for NP0002718 (L-Cysteic acid)

3D MOL for NP0002718 (L-Cysteic acid)

3D SDF for NP0002718 (L-Cysteic acid)

3D-SDF for NP0002718 (L-Cysteic acid)

PDB for NP0002718 (L-Cysteic acid)

3D PDB for NP0002718 (L-Cysteic acid)

SMILES for NP0002718 (L-Cysteic acid)

INCHI for NP0002718 (L-Cysteic acid)

Structure for NP0002718 (L-Cysteic acid)

3D Structure for NP0002718 (L-Cysteic acid)