NAV

Homocysteine

Identification

Generic Name
Homocysteine
DrugBank Accession Number
DB04422
Background

Homocysteine is a thiol-containing amino acid formed by a demethylation of methionine.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 135.185
Monoisotopic: 135.035399227
Chemical Formula
C4H9NO2S
Synonyms
  • L-2-amino-4-mercaptobutyric acid
  • L-Homocysteine
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
US-ribosylhomocysteine lyaseNot AvailableBacillus subtilis (strain 168)
U5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferaseNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
U5-methyltetrahydrofolate S-homocysteine methyltransferaseNot AvailableThermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound 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
Thia fatty acids / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Alkylthiols / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Alkylthiol / Amine / Amino acid / Carbonyl group / Carboxylic acid / Fatty acid / Fatty acyl / Hydrocarbon derivative / L-alpha-amino acid
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
homocysteine, serine family amino acid (CHEBI:17588) / Other amino acids (C00155)
Affected organisms
Not Available

Chemical Identifiers

UNII
0LVT1QZ0BA
CAS number
6027-13-0
InChI Key
FFFHZYDWPBMWHY-VKHMYHEASA-N
InChI
InChI=1S/C4H9NO2S/c5-3(1-2-8)4(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m0/s1
IUPAC Name
(2S)-2-amino-4-sulfanylbutanoic acid
SMILES
N[C@@H](CCS)C(O)=O

References

General References
Not Available
KEGG Compound
C00155
PubChem Compound
91552
PubChem Substance
46507349
ChemSpider
82666
BindingDB
50242405
ChEBI
58199
ChEMBL
CHEMBL469662
ZINC
ZINC000000895077
PDBe Ligand
HCS
Wikipedia
Homocysteine
PDB Entries
1jqw / 1jvi / 1q8a / 1q8j / 1u22 / 1xdj / 2ci5 / 2lp2 / 2n0i / 3bof …
show 29 more

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
Not AvailableCompletedScreeningOther Diseases or Conditions1
Not AvailableUnknown StatusOtherHearing Loss, Cochlear / Homocysteine / Propofol / Sevoflurane1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility14.8 mg/mLALOGPS
logP-2.3ALOGPS
logP-2.6Chemaxon
logS-0.96ALOGPS
pKa (Strongest Acidic)2.46Chemaxon
pKa (Strongest Basic)9.41Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area63.32 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity32.94 m3·mol-1Chemaxon
Polarizability13.54 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9147
Blood Brain Barrier+0.7074
Caco-2 permeable-0.7281
P-glycoprotein substrateNon-substrate0.7756
P-glycoprotein inhibitor INon-inhibitor0.9835
P-glycoprotein inhibitor IINon-inhibitor0.9807
Renal organic cation transporterNon-inhibitor0.9192
CYP450 2C9 substrateNon-substrate0.8151
CYP450 2D6 substrateNon-substrate0.7863
CYP450 3A4 substrateNon-substrate0.7887
CYP450 1A2 substrateNon-inhibitor0.9004
CYP450 2C9 inhibitorNon-inhibitor0.9439
CYP450 2D6 inhibitorNon-inhibitor0.9542
CYP450 2C19 inhibitorNon-inhibitor0.9503
CYP450 3A4 inhibitorNon-inhibitor0.9581
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9777
Ames testAMES toxic0.8982
CarcinogenicityNon-carcinogens0.8852
BiodegradationReady biodegradable0.7634
Rat acute toxicity1.4790 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9784
hERG inhibition (predictor II)Non-inhibitor0.9595
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9000000000-1f800d28bca4b2b7a49f
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-004i-0920000000-20fbffbe76510c066e6f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014l-4900000000-c50d79ba3a5013bcf29f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-9000000000-025c9e1f4fb58138c43b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-014i-4900000000-33f205e002f49f034764
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-13ea1f39ef2bd5d4d495
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-8507c9c99132719e9673
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9600000000-b9a3d1d8fe8165d1456c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-9000000000-cc5b62e9ba8c1373c15f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052b-9000000000-5c6cc246a2e1071d5c55
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-a8ca942fa95780d0ddbe
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-125.2480725
predicted
DarkChem Lite v0.1.0
[M-H]-125.2943725
predicted
DarkChem Lite v0.1.0
[M-H]-123.59751
predicted
DeepCCS 1.0 (2019)
[M+H]+125.6842725
predicted
DarkChem Lite v0.1.0
[M+H]+125.7798725
predicted
DarkChem Lite v0.1.0
[M+H]+127.163925
predicted
DeepCCS 1.0 (2019)
[M+Na]+125.4420725
predicted
DarkChem Lite v0.1.0
[M+Na]+125.4979725
predicted
DarkChem Lite v0.1.0
[M+Na]+135.74773
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. S-ribosylhomocysteine lyase
Kind
Protein
Organism
Bacillus subtilis (strain 168)
Pharmacological action
Unknown
General Function
S-ribosylhomocysteine lyase activity
Specific Function
Involved in the synthesis of autoinducer 2 (AI-2) which is secreted by bacteria and is used to communicate both the cell density and the metabolic potential of the environment. The regulation of ge...
Gene Name
luxS
Uniprot ID
O34667
Uniprot Name
S-ribosylhomocysteine lyase
Molecular Weight
17714.11 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Details2. 5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Catalyzes the transfer of a methyl group from 5-methyltetrahydrofolate to homocysteine resulting in methionine formation.
Gene Name
metE
Uniprot ID
Q9X112
Uniprot Name
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase
Molecular Weight
85570.495 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Details3. 5-methyltetrahydrofolate S-homocysteine methyltransferase
Kind
Protein
Organism
Thermotoga maritima (strain ATCC 43589 / MSB8 / DSM 3109 / JCM 10099)
Pharmacological action
Unknown
General Function
Methionine synthase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
Q9WYA5
Uniprot Name
5-methyltetrahydrofolate S-homocysteine methyltransferase
Molecular Weight
85703.315 Da

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52