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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:33:19 UTC
Update Date2019-07-23 06:05:07 UTC
HMDB IDHMDB0029895
Secondary Accession Numbers
  • HMDB29895
Metabolite Identification
Common NameD-erythro-Eritadenine
DescriptionD-erythro-Eritadenine, also known as eritadenine or D-erythro-form, belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. D-erythro-Eritadenine is a very strong basic compound (based on its pKa).
Structure
Data?1563861907
Synonyms
ValueSource
4-(6-Amino-9H-purin-9-yl)-4-deoxy-D-erythronic acidHMDB
6-Amino-alpha,beta-dihydroxy-9H-purine-9-butanoic acidHMDB
D-4-(6-Amino-9H-purin-9-yl)-4-deoxyerythronic acidHMDB
D-EritadenineHMDB
D-Erythro-formHMDB
DEAHMDB
EritadenineHMDB
LentinacinHMDB
LentysineHMDB
Eritadenine, (R-(r*,s*))-isomerMeSH
Eritadenine, (S-(r*,r*))-isomerMeSH
Eritadenine, (S-(r*,s*))-isomerMeSH
Eritadenine, monosodium salt, (R-(r*,r*))-isomerMeSH
Eritadenine, monosodium salt, (S-(r*,r*))-isomerMeSH
4-(6-Amino-9H-purin-9-yl)-2,3-dihydroxybutanoateGenerator
Chemical FormulaC9H11N5O4
Average Molecular Weight253.2147
Monoisotopic Molecular Weight253.081103865
IUPAC Name4-(6-amino-9H-purin-9-yl)-2,3-dihydroxybutanoic acid
Traditional NameD-eritadenine
CAS Registry Number23918-98-1
SMILES
NC1=NC=NC2=C1N=CN2CC(O)C(O)C(O)=O
InChI Identifier
InChI=1S/C9H11N5O4/c10-7-5-8(12-2-11-7)14(3-13-5)1-4(15)6(16)9(17)18/h2-4,6,15-16H,1H2,(H,17,18)(H2,10,11,12)
InChI KeyLIEMBEWXEZJEEZ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentLimonoids
Alternative Parents
Substituents
  • Limonoid skeleton
  • Pentacarboxylic acid or derivatives
  • Caprolactone
  • Delta valerolactone
  • Fatty acid ester
  • Delta_valerolactone
  • Oxepane
  • Fatty acyl
  • Oxane
  • Cyclic alcohol
  • Furan
  • Heteroaromatic compound
  • Tertiary alcohol
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point261 - 263 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility9.78 g/LALOGPS
logP-1.7ALOGPS
logP-3.4ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.26ChemAxon
pKa (Strongest Basic)5.13ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area147.38 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity59.58 m³·mol⁻¹ChemAxon
Polarizability22.88 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ba-9840000000-8949541137318be09e5dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0udi-6349300000-1aee357820c029208a51Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0090000000-e690b283a4a756df9493Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0970000000-55e0ea2279f0ffad12c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-4ecf3a4a52ab72994a0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0090000000-e690b283a4a756df9493Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0970000000-55e0ea2279f0ffad12c3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2900000000-4ecf3a4a52ab72994a0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pc0-1290000000-bcd7490171b5d0dda8f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0910000000-f520c1fe16b14283763dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2900000000-3638fda929f585333aeaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pc0-1290000000-bcd7490171b5d0dda8f5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0910000000-f520c1fe16b14283763dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2900000000-3638fda929f585333aeaSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001137
KNApSAcK IDNot Available
Chemspider ID2830
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2933
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

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
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. [PubMed:17139284 ]
  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. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]