Entecavir (CED0003082)

Record Information

Version

1.0

Creation Date

2016-05-22 05:44:54 UTC

Update Date

2026-05-14 16:38:57 UTC

SynCED ID

CED0003082

Secondary Accession Numbers

CHEM018998

Identification

Common Name

Entecavir

Class

Small Molecule

Description

Entecavir belongs to the nucleoside and nucleotide analogues, a class of nucleosides, nucleotides, and analogues within the organic compounds. It has a chemical formula of C12H15N5O3 and an average molecular weight of 277.28 g/mol. This compound is recorded as a source in healthcare, pharmaceuticals, and veterinary products specifically as an antiviral, with an oral exposure route. In terms of biological activity, it acts as an inhibitor of the protein target reverse transcriptase (rt).

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Baraclude	HMDB
Entecavir	ChEBI

Chemical Formula

C₁₂H₁₅N₅O₃

Average Molecular Mass

277.279 g/mol

Monoisotopic Mass

277.117 g/mol

CAS Registry Number

142217-69-4

IUPAC Name

2-amino-9-[(1S,3R,4S)-4-hydroxy-3-(hydroxymethyl)-2-methylidenecyclopentyl]-6,9-dihydro-3H-purin-6-one

Traditional Name

entecavir

SMILES

NC1=NC(=O)C2=C(N1)N(C=N2)[C@H]1C[C@H](O)[C@@H](CO)C1=C

InChI Identifier

InChI=1S/C12H15N5O3/c1-5-6(3-18)8(19)2-7(5)17-4-14-9-10(17)15-12(13)16-11(9)20/h4,6-8,18-19H,1-3H2,(H3,13,15,16,20)/t6-,7-,8-/m0/s1

InChI Key

QDGZDCVAUDNJFG-FXQIFTODSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as nucleoside and nucleotide analogues. These are analogues of nucleosides and nucleotides. These include phosphonated nucleosides, C-glycosylated nucleoside bases, analogues where the sugar unit is a pyranose, and carbocyclic nucleosides, among others.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Nucleoside and nucleotide analogues

Sub Class

Not Available

Direct Parent

Nucleoside and nucleotide analogues

Alternative Parents

Substituents

6-oxopurine
Hypoxanthine
Purinone
Purine
Imidazopyrimidine
Aminopyrimidine
Pyrimidone
Cyclopentanol
Pyrimidine
N-substituted imidazole
Azole
Cyclic alcohol
Heteroaromatic compound
Imidazole
Vinylogous amide
Secondary alcohol
Azacycle
Organoheterocyclic compound
Primary alcohol
Primary amine
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

secondary alcohol (CHEBI:473990 )
oxopurine (CHEBI:473990 )
primary alcohol (CHEBI:473990 )
2-aminopurines (CHEBI:473990 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

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	6.59 g/L	ALOGPS
logP	-0.81	ALOGPS
logP	-1.4	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	8	ChemAxon
pKa (Strongest Basic)	2.77	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71 m³·mol⁻¹	ChemAxon
Polarizability	27.31 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-001j-3190000000-4c1e30013236fcf851e8	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0a4l-4009600000-59f2f642d2b55baa6f98	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03fr-0090000000-fece17372f19f5c56b9b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03dl-4190000000-2224afe131c0d7ffddeb	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-2940000000-a8c2e92ba3db7d5cb611	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0090000000-f7f436db2922d84e90de	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0kdi-0290000000-c1ee67566ff6950ae6f0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0zfu-5930000000-de30bdfb529397180104	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-0190000000-7ffc04d8ffba36aeed92	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fb9-0590000000-1b65c7578c809b708633	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4l-3910000000-a8e292ae929a7d25bd82	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fb9-0890000000-debf13b5f5c060081554	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0fb9-0490000000-e8b9bbbb389fdfb1560f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-1920000000-f30d5851e10d4f2b16c5	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
2336.0 Log mg/kg [1300:4200]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000351	Antivirals?Antivirals are synthetic chemicals designed to inhibit the replication of viruses and are widely used in the treatment of viral infections in humans and animals.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000537	Television Systems?Television systems can be a source of synthetic chemical contamination due to the various materials and components used in their manufacture and operation.	Electrical & Electronic Equipment	PubChem
CEDs000539	Video Games?Video games, through their production and disposal processes, can be a source of synthetic chemical contamination.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	PubChem
CEDs000559	Non Electric Simulated Smoking Devices?Non-electric simulated smoking devices, often designed to mimic the experience of smoking without combustion, can be sources of synthetic chemical contamination due to the materials and chemicals used in their construction and operation.	Household cleaning & consumer products	PubChem
CEDs000560	Other Smoking Requisites?Other smoking requisites, including items such as lighters, matches, and rolling papers, can introduce synthetic chemical contamination through various components and additives.	Household cleaning & consumer products	PubChem
CEDs000563	Soap Detergents?Soap detergents are synthetic surfactants designed to enhance the cleaning efficacy of water by reducing surface tension, allowing for better interaction with dirt and grease.	Household cleaning & consumer products	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000605	Pest Repellants?Pest repellents, often formulated from synthetic chemicals, are widely used to protect crops from insect infestations and other pests.	Agriculture & land management	PubChem
CEDs000606	Plant Growth Regulators?Plant Growth Regulators (PGRs) are synthetic chemicals designed to influence the growth and development of plants.	Agriculture & land management	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000615	Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000643	Headwear?Headwear made from synthetic materials often incorporates chemicals used in the manufacturing and finishing processes, such as dyes, flame retardants, and water repellents.	Textiles, leather & furnishings	PubChem
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	PubChem
CEDs000673	Unmanned Aerial Vehicles?Unmanned Aerial Vehicles (UAVs), commonly known as drones, utilize various synthetic chemicals in their manufacturing, operation, and maintenance processes.	Aviation & Aerospace	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

3 pathwaysPathway Source: PathBank

Entecavir Action Pathway

Entecavir Drug Metabolism

Entecavir Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Cyclic di-GMP phosphodiesterase RocR	Q9HX69	Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)	Predicted (SEA)	Prediction Confidence Score 0.305 Applicability Domain 0.316 Statistical Significance 7.30e-04 Supporting Reference Compounds 2 E-value 5.68299
Click to view 3D structure	Serine/threonine protein kinase UL97	P16788	HHV-5	Predicted (SEA)	Prediction Confidence Score 0.304 Applicability Domain 0.304 Statistical Significance 1.30e-04 Supporting Reference Compounds 1 E-value 1.01204
Click to view 3D structure	Hypoxanthine-guanine phosphoribosyltransferase	P9WHQ9	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Predicted (SEA)	Prediction Confidence Score 0.288 Applicability Domain 0.311 Statistical Significance 4.20e-04 Supporting Reference Compounds 3 E-value 3.26967
Click to view 3D structure	Hypoxanthine-guanine-xanthine phosphoribosyltransferase	P20035	Plasmodium falciparum (isolate FCR-3 / Gambia)	Predicted (SEA)	Prediction Confidence Score 0.286 Applicability Domain 0.286 Low confidence Statistical Significance 3.70e-04 Supporting Reference Compounds 1 E-value 2.88042
Click to view 3D structure	Adenosine receptor A1	P25099	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.285 Applicability Domain 0.319 Statistical Significance 0.0216 Supporting Reference Compounds 221 E-value 168.31
Click to view 3D structure	Adenosylhomocysteinase	P23526	Humans	Predicted (SEA)	Prediction Confidence Score 0.28 Applicability Domain 0.303 Statistical Significance 0.0044 Supporting Reference Compounds 19 E-value 34.6429
Click to view 3D structure	Adenosylhomocysteinase	P50250	Plasmodium falciparum (isolate 3D7)	Predicted (SEA)	Prediction Confidence Score 0.278 Applicability Domain 0.338 Statistical Significance 0.0012 Supporting Reference Compounds 4 E-value 9.34191
Click to view 3D structure	Adenosine receptor A2a	P30543	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.278 Applicability Domain 0.303 Statistical Significance 0.0221 Supporting Reference Compounds 174 E-value 171.813
Click to view 3D structure	Purine nucleoside phosphorylase	P00491	Humans	Predicted (SEA)	Prediction Confidence Score 0.271 Applicability Domain 0.319 Statistical Significance 7.10e-04 Supporting Reference Compounds 19 E-value 5.52729
Click to view 3D structure	Adenosine receptor A3	P0DMS8	Humans	Predicted (SEA)	Prediction Confidence Score 0.266 Applicability Domain 0.271 Low confidence Statistical Significance 0.0705 Supporting Reference Compounds 391 E-value 548.526
Click to view 3D structure	AdoHcyase_NAD domain-containing protein	G1SVH0	Oryctolagus cuniculus	Predicted (SEA)	Prediction Confidence Score 0.263 Applicability Domain 0.265 Low confidence Statistical Significance 5.60e-04 Supporting Reference Compounds 3 E-value 4.35956
Click to view 3D structure	Adenosine receptor A2a	P29274	Humans	Predicted (SEA)	Prediction Confidence Score 0.263 Applicability Domain 0.271 Low confidence Statistical Significance 0.0638 Supporting Reference Compounds 303 E-value 496.989
Click to view 3D structure	Xanthine-guanine phosphoribosyltransferase	P0A9M5	Escherichia coli (strain K12)	Predicted (SEA)	Prediction Confidence Score 0.26 Applicability Domain 0.286 Low confidence Statistical Significance 4.80e-04 Supporting Reference Compounds 2 E-value 3.73676
Click to view 3D structure	Adenosine receptor A3	P28647	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.258 Applicability Domain 0.271 Low confidence Statistical Significance 0.0141 Supporting Reference Compounds 71 E-value 109.845
Click to view 3D structure	Heat shock protein HSP 90-alpha	P07900	Humans	Predicted (SEA)	Prediction Confidence Score 0.256 Applicability Domain 0.271 Low confidence Statistical Significance 0.0223 Supporting Reference Compounds 109 E-value 173.37
Click to view 3D structure	Endoplasmin	P14625	Humans	Predicted (SEA)	Prediction Confidence Score 0.256 Applicability Domain 0.271 Low confidence Statistical Significance 0.0073 Supporting Reference Compounds 31 E-value 57.1413
Click to view 3D structure	Adenosine receptor A1	P30542	Humans	Predicted (SEA)	Prediction Confidence Score 0.255 Applicability Domain 0.271 Low confidence Statistical Significance 0.0725 Supporting Reference Compounds 302 E-value 564.718
Click to view 3D structure	Adenosine receptor A1	P28190	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.255 Applicability Domain 0.271 Low confidence Statistical Significance 0.0162 Supporting Reference Compounds 72 E-value 126.505
Click to view 3D structure	Hypoxanthine-guanine phosphoribosyltransferase	P00492	Humans	Predicted (SEA)	Prediction Confidence Score 0.254 Applicability Domain 0.286 Low confidence Statistical Significance 4.40e-04 Supporting Reference Compounds 7 E-value 3.42537
Click to view 3D structure	Ribonuclease pancreatic	P07998	Humans	Predicted (SEA)	Prediction Confidence Score 0.253 Applicability Domain 0.253 Low confidence Statistical Significance 0.0043 Supporting Reference Compounds 1 E-value 33.553
Click to view 3D structure	Non-secretory ribonuclease	P10153	Humans	Predicted (SEA)	Prediction Confidence Score 0.253 Applicability Domain 0.253 Low confidence Statistical Significance 0.0043 Supporting Reference Compounds 1 E-value 33.553
Click to view 3D structure	Adenosine receptor A1	P47745	Cavia porcellus	Predicted (SEA)	Prediction Confidence Score 0.251 Applicability Domain 0.271 Low confidence Statistical Significance 0.0086 Supporting Reference Compounds 38 E-value 67.0282
Click to view 3D structure	S-adenosylhomocysteine hydrolase-like protein 1	O43865	Humans	Predicted (SEA)	Prediction Confidence Score 0.248 Applicability Domain 0.261 Low confidence Statistical Significance 4.70e-04 Supporting Reference Compounds 2 E-value 3.65891
Click to view 3D structure	Inosine-uridine preferring nucleoside hydrolase	Q27546	Crithidia fasciculata	Predicted (SEA)	Prediction Confidence Score 0.246 Applicability Domain 0.246 Low confidence Statistical Significance 0.0028 Supporting Reference Compounds 1 E-value 21.5642
Click to view 3D structure	Inosine-adenosine-guanosine-nucleoside hydrolase	O15727	Trypanosoma brucei brucei	Predicted (SEA)	Prediction Confidence Score 0.246 Applicability Domain 0.246 Low confidence Statistical Significance 0.0028 Supporting Reference Compounds 1 E-value 21.5642