ContaminantDB: Adefovir dipivoxil

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 05:46:04 UTC

Update Date

2016-11-09 01:15:55 UTC

Accession Number

CHEM019032

Identification

Common Name

Adefovir dipivoxil

Class

Small Molecule

Description

Adefovir dipivoxil, previously called bis-POM PMEA, with trade names Adefovir Dipivoxil and Hepsera, is an orally-administered acyclic nucleotide analog reverse transcriptase inhibitor (ntRTI) used for treatment of hepatitis B. It is ineffective against HIV-1. Adefovir dipivoxil is the diester prodrug of adefovir.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Adefovir pivoxil	Kegg
Hepsera	Kegg
Adefovir	HMDB
Adefovirdipivoxl	HMDB
ADV	HMDB
Bis-pom pmea	HMDB
GS-840	HMDB
PMEA	HMDB
Adefovir depivoxil	HMDB
9-(2-((-Bis((pivaloyloxy)methoxy)phosphinyl)methoxy)ethyl)adenine	HMDB
Preveon	HMDB

Chemical Formula

C₂₀H₃₂N₅O₈P

Average Molecular Mass

501.471 g/mol

Monoisotopic Mass

501.199 g/mol

CAS Registry Number

142340-99-6

IUPAC Name

[({[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}({[(2,2-dimethylpropanoyl)oxy]methoxy})phosphoryl)oxy]methyl 2,2-dimethylpropanoate

Traditional Name

adefovir dipivoxil

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 Key

WOZSCQDILHKSGG-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

6-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.63 g/L	ALOGPS
logP	1.49	ALOGPS
logP	3.06	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	18.59	ChemAxon
pKa (Strongest Basic)	5.13	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	166.98 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	119.99 m³·mol⁻¹	ChemAxon
Polarizability	49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4j-9715200000-be4793aa3b5324f2d049	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00b9-0291650000-bfacc10ec3119e8320f0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0kfx-1372940000-7cb1aa4d35fd2d90d7b4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00b9-0291650000-bfacc10ec3119e8320f0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1902120000-70d9218f4799e4b06e06	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0r09-4902210000-8477053656f9d74eeb50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-6910000000-ff29d5990721f46c8df5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-0309020000-13dd87f577f6eae4df2c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0903000000-3c822353c37c29284a8f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-1922000000-607d6864a8d2801ab89f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udr-5239180000-444adb50df8e9dcc8e3c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0fk9-0096000000-592e65840a6c7d4fec2b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-4972000000-f60e4d26bcfe1943e60c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0429260000-3e0596d28028aed80ce0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1389000000-87f1f9b00d5ac0c19e44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-0090000000-6582070f7152c5e52322	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00718

HMDB ID

HMDB0014856

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Vazquez E: New drug in expanded access. Posit Aware. 1998 Jan-Feb;9(1):16.

2. FDA label

Adefovir dipivoxil (CHEM019032)

Structure for CHEM019032: Adefovir dipivoxil