Adefovir

Details

• Internal ID: 0a3b3e01-3be3-47eb-9f30-baefaf897c1c
• Taxonomy: Organoheterocyclic compounds > Imidazopyrimidines > Purines and purine derivatives > 6-aminopurines
• IUPAC Name: 2-(6-aminopurin-9-yl)ethoxymethylphosphonic acid
• InChI: InChI=1S/C8H12N5O4P/c9-7-6-8(11-3-10-7)13(4-12-6)1-2-17-5-18(14,15)16/h3-4H,1-2,5H2,(H2,9,10,11)(H2,14,15,16)
• InChI Key: SUPKOOSCJHTBAH-UHFFFAOYSA-N
• Popularity: 3,397 references in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₂N₅O₄P
• Molecular Weight: 273.19 g/mol
• Exact Mass: 273.06269088 g/mol
• Topological Polar Surface Area (TPSA): 136.00 Ų
• XlogP: -2.00
• Atomic LogP (AlogP): -0.44
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 106941-25-7
• PMEA
• ((2-(6-Amino-9H-purin-9-yl)ethoxy)methyl)phosphonic acid
• 9-(2-Phosphonylmethoxyethyl)adenine
• GS 0393
• GS-0393
• 9-(2-(Phosphonomethoxy)ethyl)adenine
• GS 393
• DRG-0156
• N-(2-Phosphonylmethoxyethyl)adenine
• {[2-(6-Amino-9h-Purin-9-Yl)ethoxy]methyl}phosphonic Acid
• HSDB 8079
• UNII-6GQP90I798
• 2-(6-aminopurin-9-yl)ethoxymethylphosphonic acid
• BRN 3561094
• DTXSID6046214
• 6GQP90I798
• 9-(2-phosphonomethoxyethyl)adenine
• N-(2-Phophonomethoxyethyl-2,6-diaminopurine)
• MFCD00866943
• CHEMBL484
• Phosphonic acid, [[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]-
• CHEBI:2469
• DTXCID4026214
• Phosphonic acid, ((2-(6-amino-9H-purin-9-yl)ethoxy)methyl)-
• 106941-25-7 (free acid)
• 9-[2-(phosphonomethoxy)ethyl]adenine
• (2-(6-amino-9H-purin-9-yl)ethoxy)methylphosphonic acid
• NCGC00160539-01
• [[2-(6-Amino-9H-purin-9-yl)ethoxy]methyl]phosphonic Acid
• ADEFOVIR (MART.)
• ADEFOVIR [MART.]
• 9-[2-phosphonomethoxyethyl]adenine
• 9-PMEA
• [2-(6-amino-9H-purin-9-yl)ethoxy]methylphosphonic acid
• Adefovir [USAN:INN:BAN]
• Adefovirum
• adefovir(1-)
• Phosphonylmethoxyethyl-a
• ADEFOVIR [USAN]
• Adefovir (USAN/INN)
• ADEFOVIR [INN]
• ADEFOVIR [MI]
• ADEFOVIR [VANDF]
• AMD3100 and PMEA
• ADEFOVIR [WHO-DD]
• SCHEMBL49373
• Adefovir, >=98% (HPLC)
• J05AF08
• CHEBI:134512
• SUPKOOSCJHTBAH-UHFFFAOYSA-N
• P-[[2-(6-Amino-9H-purin-9-yl)ethoxy]methyl]phosphonic acid
• BCP22955
• HY-B1826
• 9-(2-Phosphorylmethoxyethyl)adenine
• Tox21_111882
• AC-012
• BDBM50001103
• s5068
• 9-[(2-phosphonylmethoxy)ethyl]adenine
• AKOS005259246
• DB13868
• KS-5018
• NCGC00160539-02
• BA166179
• SY015278
• CAS-106941-25-7
• CS-0013877
• FT-0601785
• 9-[3-(Phosphonomethoxy)ethyl]adenine (PMEA)
• D02768
• EN300-6733813
• A801540
• Q353551
• SR-01000945034
• Q-200594
• SR-01000945034-1
• PMEA, GS-393, 9-(2-Phosphonylmethoxyethyl)adenine
• [2-(6-Amino-purin-9-yl)-ethoxymethyl]-phosphonic acid
• Z1741977297
• Phosphonic acid, ((2-6-amino-9H-purin-9-YL)ethoxy)methyl
• ((2-(6-Amino-9H-purin-9-yl)ethoxy)-methyl)phosphonic acid
• (PMEA)[2-(6-Amino-purin-9-yl)-ethoxymethyl]-phosphonic acid
• [2-(6-Amino-purin-9-yl)-ethoxymethyl]-phosphonic acid(PMEA)
• hydrogen {[2-(6-amino-9H-purin-9-yl)ethoxy]methyl}phosphonate
• P-[[2-(6-amino-9H-purin-9-yl)ethoxy]methyl]-phosphonic acid
• ((2-6-amino-9H-purin-9-yl) ethoxy) methyl)- phosphonic acid.
• 5HG

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7876	78.76%
Caco-2	-	0.6072	60.72%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.9286	92.86%
Subcellular localzation	Mitochondria	0.3834	38.34%
OATP2B1 inhibitior	-	0.8748	87.48%
OATP1B1 inhibitior	+	0.9608	96.08%
OATP1B3 inhibitior	+	0.9418	94.18%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7067	70.67%
BSEP inhibitior	-	0.9397	93.97%
P-glycoprotein inhibitior	-	0.9344	93.44%
P-glycoprotein substrate	-	0.9362	93.62%
CYP3A4 substrate	-	0.5902	59.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8882	88.82%
CYP3A4 inhibition	-	0.8616	86.16%
CYP2C9 inhibition	-	0.7945	79.45%
CYP2C19 inhibition	-	0.8340	83.40%
CYP2D6 inhibition	-	0.8575	85.75%
CYP1A2 inhibition	-	0.7902	79.02%
CYP2C8 inhibition	-	0.8697	86.97%
CYP inhibitory promiscuity	-	0.8880	88.80%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5233	52.33%
Eye corrosion	-	0.9762	97.62%
Eye irritation	-	0.9562	95.62%
Skin irritation	-	0.7537	75.37%
Skin corrosion	-	0.9201	92.01%
Ames mutagenesis	+	0.5946	59.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.6203	62.03%
Micronuclear	+	0.8900	89.00%
Hepatotoxicity	+	0.8500	85.00%
skin sensitisation	-	0.8525	85.25%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.6836	68.36%
Acute Oral Toxicity (c)	III	0.6057	60.57%
Estrogen receptor binding	+	0.5300	53.00%
Androgen receptor binding	+	0.6721	67.21%
Thyroid receptor binding	-	0.5302	53.02%
Glucocorticoid receptor binding	-	0.6637	66.37%
Aromatase binding	+	0.5179	51.79%
PPAR gamma	-	0.6528	65.28%
Honey bee toxicity	-	0.8131	81.31%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	-	0.7652	76.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.63%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	88.83%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.41%	94.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.08%	89.34%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	84.94%	80.33%
CHEMBL3891	P07384	Calpain 1	84.72%	93.04%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.70%	95.56%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	80.31%	94.01%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 60172
• LOTUS: LTS0265395
• wikiData: Q353551