Cannabis Compound Database: Showing Compound Card for Homocysteine (CDB004862)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (7)transporters (1) Show 12 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:44:27 UTC

Updated at

2020-12-07 19:11:08 UTC

CannabisDB ID

CDB004862

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Homocysteine

Description

Homocysteine, also known as Hcy or homo-cys, 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. A homocysteine that has L configuration. Homocysteine is a very strong basic compound (based on its pKa). Homocysteine exists in all living species, ranging from bacteria to humans. Homocysteine is a potentially toxic compound. Homocysteine is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
Hcy	ChEBI
L-2-Amino-4-mercaptobutyric acid	ChEBI
L-2-Amino-4-mercaptobutyrate	Generator
2-Amino-4-mercaptobutyric acid	HMDB
Homocysteine, L isomer	HMDB
L-Isomer homocysteine	HMDB
2 Amino 4 mercaptobutyric acid	HMDB
Homocysteine, L-isomer	HMDB
(S)-2-Amino-4-mercapto-butanoate	HMDB
(S)-2-Amino-4-mercapto-butanoic acid	HMDB
(S)-2-Amino-4-mercaptobutanoic acid	HMDB
(S)-Homocysteine	HMDB
2-Amino-4-mercapto-DL-butyrate	HMDB
2-Amino-4-mercapto-DL-butyric acid	HMDB
2-Amino-4-mercapto-L-butyric acid	HMDB
2-Amino-4-mercapto-butanoate	HMDB
2-Amino-4-mercapto-butanoic acid	HMDB
2-Amino-4-mercapto-butyric acid	HMDB
2-Amino-4-sulfanylbutanoate	HMDB
2-Amino-4-sulfanylbutanoic acid	HMDB
D,L-Homocysteine	HMDB
DL-2-Amino-4-mercapto-butyric acid	HMDB
DL-2-Amino-4-mercaptobutyric acid	HMDB
DL-Homocysteine	HMDB
Homo-cys	HMDB
L-2-Amino-4-mercapto-butyric acid	HMDB
L-Homocysteine	HMDB
2-Amino-4-mercapto-butyrate	HMDB
Homocysteine	MeSH, KEGG

Chemical Formula

C₄H₉NO₂S

Average Molecular Weight

135.19

Monoisotopic Molecular Weight

135.0354

IUPAC Name

(2S)-2-amino-4-sulfanylbutanoic acid

Traditional Name

L-homocysteine

CAS Registry Number

6027-13-0

SMILES

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

InChI Identifier

InChI=1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m0/s1

InChI Key

FFFHZYDWPBMWHY-VKHMYHEASA-N

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

Substituents

L-alpha-amino acid
Thia fatty acid
Fatty acid
Fatty acyl
Amino acid
Alkylthiol
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Primary aliphatic amine
Organic oxygen compound
Carbonyl group
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

homocysteine (CHEBI:17588 )
serine family amino acid (CHEBI:17588 )
Other amino acids (C00155 )

Ontology

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Role

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	232 - 233 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	148 mg/mL	Not Available
logP	-2.56	Wikipedia

Predicted Properties

Property	Value	Source
logP	-2.3	ALOGPS
logP	-2.6	ChemAxon
logS	-0.96	ALOGPS
pKa (Strongest Acidic)	2.46	ChemAxon
pKa (Strongest Basic)	9.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	32.94 m³·mol⁻¹	ChemAxon
Polarizability	13.54 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	Homocysteine, non-derivatized, GC-MS Spectrum	splash10-004i-0920000000-20fbffbe76510c066e6f	Spectrum
Predicted GC-MS	Homocysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9000000000-1f800d28bca4b2b7a49f	Spectrum
Predicted GC-MS	Homocysteine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Homocysteine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Homocysteine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Homocysteine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Homocysteine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Homocysteine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Homocysteine, 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 - LC-ESI-ITFT , positive	splash10-014l-4900000000-c50d79ba3a5013bcf29f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-000i-9000000000-025c9e1f4fb58138c43b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-014i-4900000000-33f205e002f49f034764	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-052r-0900000000-c1f98c8182b5ddc09cb1	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00ko-9800000000-80a1c80328e8836233a4	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9100000000-1f611da44349ffdfaefe	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bvi-9000000000-c9d62a66522e46a17f56	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-3900000000-e8322d5858cba16a3bd2	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00lr-6900000000-e0190a1cc33e605bac0a	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-900bb5d8fb11bec02e39	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-38e427e24202b2411597	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-7900000000-5cf2133d9faac56032d3	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-9000000000-942ac689538269d6ca7b	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9000000000-166428542631f9ac0714	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-9bcb57b924579a6c3411	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-9000000000-8eee886864db64f3eec2	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Methionine Metabolism
Glycine and Serine Metabolism
Betaine Metabolism
Homocysteine Degradation		Not Available
Catecholamine Biosynthesis

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Methionine synthase	MTR	1q43	Q99707	details
Betaine--homocysteine S-methyltransferase 1	BHMT	5q14.1	Q93088	details
Putative adenosylhomocysteinase 3	AHCYL2	7q32.1	Q96HN2	details
Adenosylhomocysteinase	AHCY	20q11.22	P23526	details
Putative adenosylhomocysteinase 2	AHCYL1	1p13.2	O43865	details
Cystathionine beta-synthase	CBS	21q22.3	P35520	details
S-methylmethionine--homocysteine S-methyltransferase BHMT2	BHMT2	5q13	Q9H2M3	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Putative adenosylhomocysteinase 2	AHCYL1	1p13.2	O43865	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Methionine synthase	MTR	1q43	Q99707	details
Betaine--homocysteine S-methyltransferase 1	BHMT	5q14.1	Q93088	details
Cystathionine beta-synthase	CBS	21q22.3	P35520	details
S-methylmethionine--homocysteine S-methyltransferase BHMT2	BHMT2	5q13	Q9H2M3	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000742

DrugBank ID

DB04422

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Homocysteine

METLIN ID

3256

PubChem Compound

91552

PDB ID

Not Available

ChEBI ID

17588

References

General References

Not Available

Only showing the first 10 proteins. There are 12 proteins in total.

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Enzymes

Enzyme Details

1. Methionine synthase

General function:: Involved in cobalamin binding
Specific function:: Catalyzes the transfer of a methyl group from methyl-cobalamin to homocysteine, yielding enzyme-bound cob(I)alamin and methionine. Subsequently, remethylates the cofactor using methyltetrahydrofolate (By similarity).
Gene Name:: MTR
Uniprot ID:: Q99707
Molecular weight:: 140525.91

Enzyme Details

2. Betaine--homocysteine S-methyltransferase 1

General function:: Involved in zinc ion binding
Specific function:: Involved in the regulation of homocysteine metabolism. Converts betaine and homocysteine to dimethylglycine and methionine, respectively. This reaction is also required for the irreversible oxidation of choline.
Gene Name:: BHMT
Uniprot ID:: Q93088
Molecular weight:: 44998.205

Enzyme Details

3. Putative adenosylhomocysteinase 3

General function:: Involved in adenosylhomocysteinase activity
Specific function:: Not Available
Gene Name:: AHCYL2
Uniprot ID:: Q96HN2
Molecular weight:: 66592.445

Enzyme Details

4. Adenosylhomocysteinase

General function:: Involved in adenosylhomocysteinase activity
Specific function:: Adenosylhomocysteine is a competitive inhibitor of S-adenosyl-L-methionine-dependent methyl transferase reactions; therefore adenosylhomocysteinase may play a key role in the control of methylations via regulation of the intracellular concentration of adenosylhomocysteine.
Gene Name:: AHCY
Uniprot ID:: P23526
Molecular weight:: 47715.715

Enzyme Details

5. Putative adenosylhomocysteinase 2

General function:: Involved in adenosylhomocysteinase activity
Specific function:: Not Available
Gene Name:: AHCYL1
Uniprot ID:: O43865
Molecular weight:: 53753.0

Enzyme Details

6. 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

Enzyme Details

7. S-methylmethionine--homocysteine S-methyltransferase BHMT2

General function:: Involved in zinc ion binding
Specific function:: Involved in the regulation of homocysteine metabolism. Converts homocysteine to methionine using S-methylmethionine (SMM) as a methyl donor.
Gene Name:: BHMT2
Uniprot ID:: Q9H2M3
Molecular weight:: 33166.69

Transporters

Enzyme Details

1. Putative adenosylhomocysteinase 2

General function:: Involved in adenosylhomocysteinase activity
Specific function:: Not Available
Gene Name:: AHCYL1
Uniprot ID:: O43865
Molecular weight:: 53753.0

Only showing the first 10 proteins. There are 12 proteins in total.

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Showing Compound Card for Homocysteine (CDB004862)

Structure for CDB004862 (Homocysteine)

Enzymes

Transporters