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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-17 15:35:22 UTC
Update Date2020-02-26 21:23:36 UTC
HMDB IDHMDB0001915
Secondary Accession Numbers
  • HMDB01915
Metabolite Identification
Common NameAlendronic acid
DescriptionAlendronic acid, also known as alendronate or acido alendronico, belongs to the class of organic compounds known as bisphosphonates. These are organic compounds containing two phosphonate groups linked together through a carbon atoms. In humans, alendronic acid is involved in the alendronate action pathway. Alendronic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make alendronic acid a potential biomarker for the consumption of these foods. Alendronic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Alendronic acid.
Structure
Data?1582752216
Synonyms
ValueSource
(4-Amino-1-hydroxybutylidene)bisphosphonic acidChEBI
Acide alendroniqueChEBI
Acido alendronicoChEBI
Acidum alendronicumChEBI
AlendronateChEBI
(4-Amino-1-hydroxybutylidene)bisphosphonateGenerator
4-Amino-1-hydroxybutylidene 1,1-biphosphonateMeSH
Alendronate monosodium salt, trihydrateMeSH
Alendronate sodiumMeSH
Aminohydroxybutane bisphosphonateMeSH
FosamaxMeSH
Alendronate sodium hydrateHMDB
Sodium, alendronateMeSH, HMDB
4 amino 1 Hydroxybutylidene 1,1 biphosphonateMeSH, HMDB
Bisphosphonate, aminohydroxybutaneMeSH, HMDB
Chemical FormulaC4H13NO7P2
Average Molecular Weight249.096
Monoisotopic Molecular Weight249.016724799
IUPAC Name(4-amino-1-hydroxy-1-phosphonobutyl)phosphonic acid
Traditional Namealendronate
CAS Registry Number66376-36-1
SMILES
NCCCC(O)(P(O)(O)=O)P(O)(O)=O
InChI Identifier
InChI=1S/C4H13NO7P2/c5-3-1-2-4(6,13(7,8)9)14(10,11)12/h6H,1-3,5H2,(H2,7,8,9)(H2,10,11,12)
InChI KeyOGSPWJRAVKPPFI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bisphosphonates. These are organic compounds containing two phosphonate groups linked together through a carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphonic acids and derivatives
Sub ClassBisphosphonates
Direct ParentBisphosphonates
Alternative Parents
Substituents
  • Bisphosphonate
  • Organophosphonic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organophosphorus compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility16.9 g/LALOGPS
logP-1.3ALOGPS
logP-4.2ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)0.69ChemAxon
pKa (Strongest Basic)9.91ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area161.31 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity47.37 m³·mol⁻¹ChemAxon
Polarizability19.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available153.26731661259
DarkChem[M-H]-PredictedNot Available147.1231661259
AllCCS[M+H]+PredictedNot Available150.67632859911
AllCCS[M-H]-PredictedNot Available141.19632859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Alendronic acid,1TMS,#12323.4194https://arxiv.org/abs/1905.12712
Alendronic acid,1TMS,#22302.8345https://arxiv.org/abs/1905.12712
Alendronic acid,1TMS,#32371.831https://arxiv.org/abs/1905.12712
Alendronic acid,1TBDMS,#12563.9644https://arxiv.org/abs/1905.12712
Alendronic acid,1TBDMS,#22535.0369https://arxiv.org/abs/1905.12712
Alendronic acid,1TBDMS,#32637.2874https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9010000000-6b540b3cfe12455ee0472017-08-28View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-9020000000-f4a0f6418448b21083712017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-2930000000-99692afb4ed2532519472012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-0900000000-d2c07307d66e1c7d52e82012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0kdl-9500000000-c82a6e6e898154627c7d2012-07-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ue9-0590000000-ed1b4585584330309b422017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uyi-4900000000-42101c55bda7e112b2af2017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-9330000000-8ac66f69531027a0950f2017-07-25View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kb-2590000000-2c9bde6c398541c5cb712017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-017i-6950000000-d1f8822b01485883083d2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9000000000-7b5e5c1f9b218640040b2017-07-26View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Intestine
  • Prostate
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00630
Phenol Explorer Compound IDNot Available
FooDB IDFDB022734
KNApSAcK IDNot Available
Chemspider ID2004
KEGG Compound IDC07752
BioCyc IDALENDRONATE
BiGG IDNot Available
Wikipedia LinkAlendronic_acid
METLIN ID818
PubChem Compound2088
PDB IDNot Available
ChEBI ID2567
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Virtanen SS, Vaananen HK, Harkonen PL, Lakkakorpi PT: Alendronate inhibits invasion of PC-3 prostate cancer cells by affecting the mevalonate pathway. Cancer Res. 2002 May 1;62(9):2708-14. [PubMed:11980672 ]
  2. Ezra A, Hoffman A, Breuer E, Alferiev IS, Monkkonen J, El Hanany-Rozen N, Weiss G, Stepensky D, Gati I, Cohen H, Tormalehto S, Amidon GL, Golomb G: A peptide prodrug approach for improving bisphosphonate oral absorption. J Med Chem. 2000 Oct 5;43(20):3641-52. [PubMed:11020278 ]
  3. Cremers SC, van Hogezand R, Banffer D, den Hartigh J, Vermeij P, Papapoulos SE, Hamdy NA: Absorption of the oral bisphosphonate alendronate in osteoporotic patients with Crohn's disease. Osteoporos Int. 2005 Dec;16(12):1727-30. Epub 2005 Jun 15. [PubMed:15959617 ]
  4. Sarno M, Sarno L, Baylink D, Drinkwater B, Farley S, Kleerekoper M, Lang R, Lappe J, Licata A, McClung M, Miller P, Nattrass S, Recker R, Schwartz EN, Tucci JR, Wolf S, Powell H, Tjersland G, Warnick GR: Excretion of sweat and urine pyridinoline crosslinks in healthy controls and subjects with established metabolic bone disease. Clin Chem Lab Med. 2001 Mar;39(3):223-8. [PubMed:11350019 ]
  5. Rossini M, Gatti D, Isaia G, Sartori L, Braga V, Adami S: Effects of oral alendronate in elderly patients with osteoporosis and mild primary hyperparathyroidism. J Bone Miner Res. 2001 Jan;16(1):113-9. [PubMed:11149474 ]
  6. Makowski GS, Ramsby ML: Autoactivation profiles of calcium-dependent matrix metalloproteinase-2 and -9 in inflammatory synovial fluid: effect of pyrophosphate and bisphosphonates. Clin Chim Acta. 2005 Aug;358(1-2):182-91. [PubMed:15921672 ]
  7. Yalcin F, Gurgan S, Gurgan T: The effect of menopause, hormone replacement therapy (HRT), alendronate (ALN), and calcium supplements on saliva. J Contemp Dent Pract. 2005 May 15;6(2):10-7. [PubMed:15915200 ]
  8. Rudge S, Hailwood S, Horne A, Lucas J, Wu F, Cundy T: Effects of once-weekly oral alendronate on bone in children on glucocorticoid treatment. Rheumatology (Oxford). 2005 Jun;44(6):813-8. Epub 2005 Feb 3. [PubMed:15695300 ]
  9. Ravn P, Thompson DE, Ross PD, Christiansen C: Biochemical markers for prediction of 4-year response in bone mass during bisphosphonate treatment for prevention of postmenopausal osteoporosis. Bone. 2003 Jul;33(1):150-8. [PubMed:12919710 ]
  10. Chesnut CH 3rd, Harris ST: Short-term effect of alendronate on bone mass and bone remodeling in postmenopausal women. Osteoporos Int. 1993;3 Suppl 3:S17-9. [PubMed:8298198 ]
  11. Yun MH, Kwon KI: High-performance liquid chromatography method for determining alendronate sodium in human plasma by detecting fluorescence: application to a pharmacokinetic study in humans. J Pharm Biomed Anal. 2006 Jan 23;40(1):168-72. Epub 2005 Aug 10. [PubMed:16095861 ]