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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:46 UTC
HMDB IDHMDB0014856
Secondary Accession Numbers
  • HMDB14856
Metabolite Identification
Common NameAdefovir Dipivoxil
DescriptionAdefovir Dipivoxil is only found in individuals that have used or taken this drug.Adefovir dipivoxil, previously called bis-POM PMEA, with trade names Preveon and Hepsera, is an orally-administered nucleotide analog reverse transcriptase inhibitor (ntRTI) used for treatment of hepatitis B. It is a failed treatment for HIV. [Wikipedia ]Adefovir dipivoxil is a prodrug of adefovir. Adefovir is an acyclic nucleotide analog of adenosine monophosphate which is phosphorylated to the active metabolite adefovir diphosphate by cellular kinases. Adefovir diphosphate inhibits HBV DNA polymerase (reverse transcriptase) by competing with the natural substrate deoxyadenosine triphosphate and by causing DNA chain termination after its incorporation into viral DNA. The inhibition constant (Ki) for adefovir diphosphate for HBV DNA polymerase was 0.1 μM. Adefovir diphosphate is a weak inhibitor of human DNA polymerases alpha and gamma with Ki values of 1.18 μM and 0.97μM, respectively.
Structure
Data?1582753228
Synonyms
ValueSource
Adefovir pivoxilKegg
HepseraKegg
AdefovirHMDB
AdefovirdipivoxlHMDB
ADVHMDB
Bis-pom pmeaHMDB
GS-840HMDB
PMEAHMDB
Adefovir depivoxilHMDB
9-(2-((-Bis((pivaloyloxy)methoxy)phosphinyl)methoxy)ethyl)adenineHMDB
PreveonHMDB
Chemical FormulaC20H32N5O8P
Average Molecular Weight501.4705
Monoisotopic Molecular Weight501.198849537
IUPAC Name[({[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}({[(2,2-dimethylpropanoyl)oxy]methoxy})phosphoryl)oxy]methyl 2,2-dimethylpropanoate
Traditional Nameadefovir dipivoxil
CAS Registry Number142340-99-6
SMILES
CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N)N=CN=C12)OCOC(=O)C(C)(C)C
InChI Identifier
InChI=1S/C20H32N5O8P/c1-19(2,3)17(26)30-11-32-34(28,33-12-31-18(27)20(4,5)6)13-29-8-7-25-10-24-14-15(21)22-9-23-16(14)25/h9-10H,7-8,11-13H2,1-6H3,(H2,21,22,23)
InChI KeyWOZSCQDILHKSGG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-aminopurines
Alternative Parents
Substituents
  • 6-aminopurine
  • Aminopyrimidine
  • Dialkyl alkylphosphonate
  • Phosphonic acid diester
  • Dicarboxylic acid or derivatives
  • Imidolactam
  • Pyrimidine
  • Phosphonic acid ester
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Organophosphonic acid derivative
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Azacycle
  • Organophosphorus compound
  • Primary amine
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.63 g/LNot Available
LogP0.8Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.63 g/LALOGPS
logP1.49ALOGPS
logP3.06ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)18.59ChemAxon
pKa (Strongest Basic)5.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area166.98 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity119.99 m³·mol⁻¹ChemAxon
Polarizability49 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+213.38931661259
DarkChem[M-H]-204.65631661259
DeepCCS[M-2H]-242.38530932474
DeepCCS[M+Na]+217.8130932474
AllCCS[M+H]+210.932859911
AllCCS[M+H-H2O]+209.532859911
AllCCS[M+NH4]+212.332859911
AllCCS[M+Na]+212.732859911
AllCCS[M-H]-210.532859911
AllCCS[M+Na-2H]-212.032859911
AllCCS[M+HCOO]-213.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Adefovir DipivoxilCC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N)N=CN=C12)OCOC(=O)C(C)(C)C3756.4Standard polar33892256
Adefovir DipivoxilCC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N)N=CN=C12)OCOC(=O)C(C)(C)C3041.9Standard non polar33892256
Adefovir DipivoxilCC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N)N=CN=C12)OCOC(=O)C(C)(C)C3346.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Adefovir Dipivoxil,1TMS,isomer #1CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C3311.3Semi standard non polar33892256
Adefovir Dipivoxil,1TMS,isomer #1CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C3239.4Standard non polar33892256
Adefovir Dipivoxil,1TMS,isomer #1CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C5496.1Standard polar33892256
Adefovir Dipivoxil,2TMS,isomer #1CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C3275.4Semi standard non polar33892256
Adefovir Dipivoxil,2TMS,isomer #1CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C3301.7Standard non polar33892256
Adefovir Dipivoxil,2TMS,isomer #1CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C4718.8Standard polar33892256
Adefovir Dipivoxil,1TBDMS,isomer #1CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C3457.5Semi standard non polar33892256
Adefovir Dipivoxil,1TBDMS,isomer #1CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C3411.3Standard non polar33892256
Adefovir Dipivoxil,1TBDMS,isomer #1CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C5392.0Standard polar33892256
Adefovir Dipivoxil,2TBDMS,isomer #1CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C3610.2Semi standard non polar33892256
Adefovir Dipivoxil,2TBDMS,isomer #1CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C3625.3Standard non polar33892256
Adefovir Dipivoxil,2TBDMS,isomer #1CC(C)(C)C(=O)OCOP(=O)(COCCN1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21)OCOC(=O)C(C)(C)C4661.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Adefovir Dipivoxil GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4j-9715200000-be4793aa3b5324f2d0492017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Adefovir Dipivoxil LC-ESI-qTof , Positive-QTOFsplash10-00b9-0291650000-bfacc10ec3119e8320f02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adefovir Dipivoxil , positive-QTOFsplash10-0kfx-1372940000-7cb1aa4d35fd2d90d7b42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Adefovir Dipivoxil , positive-QTOFsplash10-00b9-0291650000-bfacc10ec3119e8320f02017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adefovir Dipivoxil 10V, Positive-QTOFsplash10-0udi-1902120000-70d9218f4799e4b06e062016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adefovir Dipivoxil 20V, Positive-QTOFsplash10-0r09-4902210000-8477053656f9d74eeb502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adefovir Dipivoxil 40V, Positive-QTOFsplash10-0a4r-6910000000-ff29d5990721f46c8df52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adefovir Dipivoxil 10V, Negative-QTOFsplash10-0f6t-0309020000-13dd87f577f6eae4df2c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adefovir Dipivoxil 20V, Negative-QTOFsplash10-0udi-0903000000-3c822353c37c29284a8f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adefovir Dipivoxil 40V, Negative-QTOFsplash10-001i-1922000000-607d6864a8d2801ab89f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adefovir Dipivoxil 10V, Positive-QTOFsplash10-0udr-5239180000-444adb50df8e9dcc8e3c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adefovir Dipivoxil 20V, Positive-QTOFsplash10-0fk9-0096000000-592e65840a6c7d4fec2b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adefovir Dipivoxil 40V, Positive-QTOFsplash10-000i-4972000000-f60e4d26bcfe1943e60c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adefovir Dipivoxil 10V, Negative-QTOFsplash10-0udi-0429260000-3e0596d28028aed80ce02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adefovir Dipivoxil 20V, Negative-QTOFsplash10-0udi-1389000000-87f1f9b00d5ac0c19e442021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Adefovir Dipivoxil 40V, Negative-QTOFsplash10-00di-0090000000-6582070f7152c5e523222021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00718 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00718 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00718
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID54855
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAdefovir
METLIN IDNot Available
PubChem Compound60871
PDB IDNot Available
ChEBI ID183515
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Vazquez E: New drug in expanded access. Posit Aware. 1998 Jan-Feb;9(1):16. [PubMed:11364994 ]
  2. (). FDA label . .

Transporters

General function:
Involved in ATP binding
Specific function:
May be an organic anion pump relevant to cellular detoxification
Gene Name:
ABCC4
Uniprot ID:
O15439
Molecular weight:
149525.3
References
  1. Schuetz JD, Connelly MC, Sun D, Paibir SG, Flynn PM, Srinivas RV, Kumar A, Fridland A: MRP4: A previously unidentified factor in resistance to nucleoside-based antiviral drugs. Nat Med. 1999 Sep;5(9):1048-51. [PubMed:10470083 ]
General function:
Involved in ATP binding
Specific function:
Acts as a multispecific organic anion pump which can transport nucleotide analogs
Gene Name:
ABCC5
Uniprot ID:
O15440
Molecular weight:
160658.8
References
  1. Wijnholds J, Mol CA, van Deemter L, de Haas M, Scheffer GL, Baas F, Beijnen JH, Scheper RJ, Hatse S, De Clercq E, Balzarini J, Borst P: Multidrug-resistance protein 5 is a multispecific organic anion transporter able to transport nucleotide analogs. Proc Natl Acad Sci U S A. 2000 Jun 20;97(13):7476-81. [PubMed:10840050 ]
General function:
Involved in transmembrane transport
Specific function:
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain
Gene Name:
SLC22A3
Uniprot ID:
O75751
Molecular weight:
61279.5
References
  1. Grundemann D, Schechinger B, Rappold GA, Schomig E: Molecular identification of the corticosterone-sensitive extraneuronal catecholamine transporter. Nat Neurosci. 1998 Sep;1(5):349-51. [PubMed:10196521 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Cihlar T, Ho ES: Fluorescence-based assay for the interaction of small molecules with the human renal organic anion transporter 1. Anal Biochem. 2000 Jul 15;283(1):49-55. [PubMed:10929807 ]
  2. Cihlar T, Lin DC, Pritchard JB, Fuller MD, Mendel DB, Sweet DH: The antiviral nucleotide analogs cidofovir and adefovir are novel substrates for human and rat renal organic anion transporter 1. Mol Pharmacol. 1999 Sep;56(3):570-80. [PubMed:10462545 ]
  3. Ho ES, Lin DC, Mendel DB, Cihlar T: Cytotoxicity of antiviral nucleotides adefovir and cidofovir is induced by the expression of human renal organic anion transporter 1. J Am Soc Nephrol. 2000 Mar;11(3):383-93. [PubMed:10703662 ]