Cannabis Compound Database: Showing Compound Card for L-Cystathionine (CDB005143)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (2) Show 4 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:13:40 UTC

Updated at

2020-12-07 19:11:40 UTC

CannabisDB ID

CDB005143

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

L-Cystathionine

Description

L-Cystathionine 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. L-Cystathionine is a very strong basic compound (based on its pKa). L-Cystathionine exists in all living species, ranging from bacteria to humans. Within humans, L-cystathionine participates in a number of enzymatic reactions. In particular, L-cystathionine can be converted into L-cysteine and 2-ketobutyric acid; which is mediated by the enzyme cystathionine gamma-lyase. In addition, L-cystathionine can be biosynthesized from L-homoserine and L-serine through its interaction with the enzyme cystathionine beta-synthase. In humans, L-cystathionine is involved in methionine metabolism. L-Cystathionine is a potentially toxic compound. L-Cystathionine, with regard to humans, has been found to be associated with several diseases such as eosinophilic esophagitis, alzheimer's disease, and autism; L-cystathionine has also been linked to several inborn metabolic disorders including hypermethioninemia and folate deficiency. A modified amino acid generated by enzymic means from L-homocysteine and L-serine. L-Cystathionine is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-S-(2-Amino-2-carboxyethyl)-L-homocysteine	ChEBI
L-(+)-Cystathionine	ChEBI
S-(beta-Amino-beta-carboxyethyl)homocysteine	ChEBI
S-(b-Amino-b-carboxyethyl)homocysteine	Generator
S-(Β-amino-β-carboxyethyl)homocysteine	Generator
Cystathionine	HMDB
S-[(2R)-2-Amino-2-carboxyethyl]-L-homocysteine	HMDB
[R-(R,s)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-butanoate	HMDB
[R-(R,s)]-2-amino-4-[(2-amino-2-carboxyethyl)thio]-butanoic acid	HMDB

Chemical Formula

C₇H₁₄N₂O₄S

Average Molecular Weight

222.26

Monoisotopic Molecular Weight

222.0674

IUPAC Name

(2S)-2-amino-4-{[(2R)-2-amino-2-carboxyethyl]sulfanyl}butanoic acid

Traditional Name

L-cystathionine

CAS Registry Number

56-88-2

SMILES

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

InChI Identifier

InChI=1S/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1

InChI Key

ILRYLPWNYFXEMH-WHFBIAKZSA-N

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
Thia fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Amino acid
Carboxylic acid
Thioether
Dialkylthioether
Sulfenyl compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

cystathionine (CHEBI:17482 )

Ontology

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Organ and components:

Biofluid and excreta:

Subcellular:

Cytoplasm

Role

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	312 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	22 mg/mL	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-4	ALOGPS
logP	-5.8	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	1.79	ChemAxon
pKa (Strongest Basic)	9.66	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	126.64 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	51.57 m³·mol⁻¹	ChemAxon
Polarizability	22.02 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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	L-Cystathionine, 4 TMS, GC-MS Spectrum	splash10-00fr-8950000000-640b4294e37e5a01048d	Spectrum
GC-MS	L-Cystathionine, 2 TMS, GC-MS Spectrum	splash10-0f7c-7910000000-91f9f2b2dd44a3cdb276	Spectrum
GC-MS	L-Cystathionine, 3 TMS, GC-MS Spectrum	splash10-00or-1940000000-c0d688e4ea87ff3e03fa	Spectrum
GC-MS	L-Cystathionine, 4 TMS, GC-MS Spectrum	splash10-00or-0980000000-7d816de782a902900d0e	Spectrum
GC-MS	L-Cystathionine, non-derivatized, GC-MS Spectrum	splash10-00fr-8950000000-640b4294e37e5a01048d	Spectrum
GC-MS	L-Cystathionine, non-derivatized, GC-MS Spectrum	splash10-0f7c-7910000000-91f9f2b2dd44a3cdb276	Spectrum
GC-MS	L-Cystathionine, non-derivatized, GC-MS Spectrum	splash10-00or-1940000000-c0d688e4ea87ff3e03fa	Spectrum
GC-MS	L-Cystathionine, non-derivatized, GC-MS Spectrum	splash10-00or-0980000000-7d816de782a902900d0e	Spectrum
Predicted GC-MS	L-Cystathionine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9410000000-9487e9168e86a2297931	Spectrum
Predicted GC-MS	L-Cystathionine, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dm-9665000000-608a6335880ad1c2519d	Spectrum
Predicted GC-MS	L-Cystathionine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystathionine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystathionine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystathionine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystathionine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystathionine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystathionine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystathionine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystathionine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystathionine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystathionine, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystathionine, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystathionine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystathionine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Cystathionine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0089-1980000000-99cb7d1da067e5436b09	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9200000000-fb776970b6ef36e72725	Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9200000000-fb776970b6ef36e72725	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-00fr-0690000000-0b572de3fcbc7e2f13cc	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000t-0900000000-5788192b32aadd177e33	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-000b-4900000000-b86ac7de446a762365bd	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-000j-9800000000-75ff1bc6e325692a9da9	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-00kr-9100000000-6517562dc0f31a85afc8	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-001i-0900000000-d1628d0a880f1b6e6d90	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000i-9000000000-9a2e1e54b77216e2df72	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-00di-0090000000-36678c2f0bf1b01cc9d4	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-05fr-0190000000-e575f57f0d76ef6afa49	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-00e9-0940000000-962ae510f06296b98878	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-00e9-0940000000-27da1912eac54f485bfa	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00fr-0690000000-82fe2198c98660008c04	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000t-0900000000-58cceb69cceeff79606c	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000b-4900000000-5877787c54120dc165c9	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000j-9800000000-fd29b0fcf62b73831829	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-00kr-9100000000-6517562dc0f31a85afc8	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05di-1930000000-887e3ad7da04e4f1aac9	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01uc-6900000000-563444ac8ab717997268	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0uki-9700000000-35397d8e2ab2c6582c52	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0970000000-d0f0a96ca41d1f751c26	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0089-3910000000-22200c974305822456d8	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-008l-9300000000-0dfaab5efe3438889c3c	Spectrum

NMR

Type	Description	View
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
1D NMR	1H NMR Spectrum	Spectrum
1D NMR	13C NMR Spectrum	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Glycine and Serine Metabolism
Methionine Metabolism
Homocysteine Degradation		Not Available
Gamma-cystathionase deficiency (CTH)		Not Available
Homocystinuria, cystathionine beta-synthase deficiency		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Cystathionine gamma-lyase	CTH	1p31.1	P32929	details
Cystathionine beta-synthase	CBS	21q22.3	P35520	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Cystathionine beta-synthase	CBS	21q22.3	P35520	details

Receptors

Not Available

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Cystathionine gamma-lyase	CTH	1p31.1	P32929	details

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000099

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

439258

PDB ID

Not Available

ChEBI ID

17482

References

General References

Not Available

Enzymes

Enzyme Details

1. Cystathionine gamma-lyase

General function:: Involved in pyridoxal phosphate binding
Specific function:: Catalyzes the last step in the trans-sulfuration pathway from methionine to cysteine. Has broad substrate specificity. Converts cystathionine to cysteine, ammonia and 2-oxobutanoate. Converts two cysteine molecules to lanthionine and hydrogen sulfide. Can also accept homocysteine as substrate. Specificity depends on the levels of the endogenous substrates. Generates the endogenous signaling molecule hydrogen sulfide (H2S), and so contributes to the regulation of blood pressure. Acts as a cysteine-protein sulfhydrase by mediating sulfhydration of target proteins: sulfhydration consists of converting -SH groups into -SSH on specific cysteine residues of target proteins such as GAPDH, PTPN1 and NF-kappa-B subunit RELA, thereby regulating their function.
Gene Name:: CTH
Uniprot ID:: P32929
Molecular weight:: 41259.91

Enzyme Details

2. Cystathionine beta-synthase

General function:: Involved in cysteine biosynthetic process from serine
Specific function:: Only known pyridoxal phosphate-dependent enzyme that contains heme. Important regulator of hydrogen sulfide, especially in the brain, utilizing cysteine instead of serine to catalyze the formation of hydrogen sulfide. Hydrogen sulfide is a gastratransmitter with signaling and cytoprotective effects such as acting as a neuromodulator in the brain to protect neurons against hypoxic injury (By similarity).
Gene Name:: CBS
Uniprot ID:: P35520
Molecular weight:: 60586.05

Showing Compound Card for L-Cystathionine (CDB005143)

Structure for CDB005143 (L-Cystathionine)

Enzymes