Compound Detail

CHEMBL752

ADENOSINE PHOSPHATE

💊 Approved Drug

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💊 Approved Drug

Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL752
Name	ADENOSINE PHOSPHATE
Phase	Approved
Structure Type	MOL
InChI Key	UDMBCSSLTHHNCD-KQYNXXCUSA-N

Known Names

5'-adenylic acid A 5MP A-5MP Adenosine 5'-monophosphoric acid Adenosine monophosphate (amp) Adenosine phosphate Adenyl Fosfato de adenosina NSC-20264 Phosphate d'adenosine Vitamin b8

Targets

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Mechanisms

Molecular Properties

347.2

MW (Da)

-1.86

ALogP

HBA

HBD

186.1

PSA (Å²)

0.39

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Availability	Withdrawn
Chirality	Single Enantiomer

Flags

Withdrawn Natural Product

USAN Stem	-nosine
USAN Year	1963

Extended Properties

Molecular Formula	C10H14N5O7P
MW	347.22
Aromatic Rings	2
Heavy Atoms	23
NP-Likeness	1.30

Mechanism of Action

Mechanism	Action Type	Target	Direct	Efficacy
Unknown	-	-	✓	✓

Indications

Ischemia

Drug Warnings

Withdrawn

General Warning

Not safe or effective for intended use as vasodilator, anti-inflammatory

Country: United States Year: 1973

Withdrawn

General Warning

Not safe or effective for intended use as vasodilator, anti-inflammatory

Country: United States Year: 1973

Activity Summary

IC50 26 meas. best 7.0

EC50 15 meas. best 7.07

Kd 12 meas. best 8.95

Ki 8 meas. best 9.64

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Human immunodeficiency virus type 1 protease CHEMBL243	Ki	9.64	9.64	0.2	1
Human immunodeficiency virus type 1 protease CHEMBL243	Kd	8.95	8.95	1.1	1
P2Y purinoceptor 2 CHEMBL4398	EC50	7.07	6.25	85.0	2
Proto-oncogene tyrosine-protein kinase Src CHEMBL267	IC50	7.0	7.0	100.0	1
Fructose-1,6-bisphosphatase 1 CHEMBL3975	IC50	6.85	5.82	140.0	13
AMP-activated protein kinase, AMPK CHEMBL2096907	Kd	6.82	6.82	150.0	1
Unchecked CHEMBL612545	IC50	6.52	5.7167	300.0	6
Adenosine receptor A1 CHEMBL226	EC50	6.3	6.3	500.0	1
Fructose-1,6-bisphosphatase 1 CHEMBL2263	IC50	5.89	5.89	1300.0	2
Unchecked CHEMBL612545	EC50	5.85	5.825	1400.0	2
AMPK alpha2/beta1/gamma1 CHEMBL3038455	EC50	5.85	5.85	1400.0	1
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 CHEMBL2111345	EC50	5.82	4.985	1519.0	2
P2Y purinoceptor 1 CHEMBL4315	EC50	5.82	5.48	1500.0	2
No relevant target CHEMBL2362975	Kd	5.57	5.57	2700.0	1
P2Y purinoceptor 1 CHEMBL5720	EC50	5.55	5.505	2800.0	2
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1 CHEMBL2111345	Kd	5.43	5.43	3700.0	1
Unchecked CHEMBL612545	Kd	5.27	5.0	5400.0	5
AMP-activated protein kinase, AMPK CHEMBL2096907	EC50	5.23	5.23	5900.0	1
T1R1/T1R3 CHEMBL3832641	EC50	4.96	4.96	11000.0	1
P2Y purinoceptor 11 CHEMBL4867	EC50	4.76	4.76	17250.0	1
5-hydroxymethyl-dUMP N-hydrolase CHEMBL3351218	Ki	4.72	4.72	19200.0	1
Alcohol dehydrogenase CHEMBL2111372	Ki	4.42	4.42	38000.0	1
5-hydroxymethyl-dUMP N-hydrolase CHEMBL3329079	Ki	4.4	4.4	40000.0	1
Transient receptor potential cation channel subfamily M member 2 CHEMBL1250402	IC50	4.16	4.16	70000.0	2
Adenylate kinase 2, mitochondrial CHEMBL2376	Ki	4.1	4.1	80000.0	1
L-lactate dehydrogenase A chain CHEMBL4835	Kd	3.19	3.19	650000.0	1
2-dehydropantoate 2-reductase CHEMBL4855	Ki	2.2	2.2	6300000.0	1

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Human immunodeficiency virus type 1 protease	Ki	=	0.23	nM	9.64	Inhibition constant against HIV-1 Protease	12459011
Human immunodeficiency virus type 1 protease	Kd	=	1.13	nM	8.95	Equilibrium constant for the interaction between inhibitor and HIV-1 Protease	12459011
P2Y purinoceptor 2	EC50	=	85.0	nM	7.07	Measure of Agonist Potency at human P2Y purinoceptor 2 (hP2Y2) stably expressed ...	11754592
Proto-oncogene tyrosine-protein kinase Src	IC50	=	100.0	nM	7.0	Inhibition of p60c-src expressed in chick embryo fibroblast	1479375
Fructose-1,6-bisphosphatase 1	IC50	=	140.0	nM	6.85	Inhibition of FBPase in human liver using fructose-2,6phosphate as a substrate	19969452
AMP-activated protein kinase, AMPK	Kd	=	150.0	nM	6.82	Binding affinity to truncated AMPK (unknown origin) assessed as dissociation con...	38739840
Unchecked	IC50	=	300.0	nM	6.52	Inhibition of Rous sarcoma virus p60 v-src-induced IgG phosphorylation in tumor ...	1479375
Fructose-1,6-bisphosphatase 1	IC50	=	440.0	nM	6.36	Inhibition of FBPase in human liver	19969452
Adenosine receptor A1	EC50	=	500.0	nM	6.3	Agonist activity at human A1AR expressed in HEK293T/17 cells assessed as inhibit...	22738238
Fructose-1,6-bisphosphatase 1	IC50	=	800.0	nM	6.1	Concentration required to inhibit the human liver recombinant fructose-1,6-bisph...	11140724
Fructose-1,6-bisphosphatase 1	IC50	=	1000.0	nM	6.0	Inhibition of human liver FBPase expressed in Escherichia coli by spectrophotome...	19348494
Unchecked	IC50	=	1000.0	nM	6.0	Inhibition of rat FBPase	24900234
Fructose-1,6-bisphosphatase 1	IC50	=	1000.0	nM	6.0	Inhibition of FBPase (unknown origin)	-
Fructose-1,6-bisphosphatase 1	IC50	=	1000.0	nM	6.0	Inhibition of human liver FBPase expressed in Escherichia coli by spectrophotome...	29055870
Fructose-1,6-bisphosphatase 1	IC50	=	1300.0	nM	5.89	Inhibition of pig kidney fructose-1,6-bisphosphatase expressed in Escherichia co...	20116906
Fructose-1,6-bisphosphatase 1	IC50	=	1300.0	nM	5.89	Inhibition of pig FBPase expressed in Escherichia coli EK1601 by spectrophotomet...	19419876
Unchecked	IC50	=	1300.0	nM	5.89	Inhibition of human recombinant FBPase-mediated fructose-6-phosphate formation b...	24946215
Unchecked	EC50	=	1400.0	nM	5.85	Activation of rat GPPase	24900234
AMPK alpha2/beta1/gamma1	EC50	=	1400.0	nM	5.85	Allosteric activation of AMPK alpha2/beta1/gamma1 in human HepG2 cells by scinti...	31744674
AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1	EC50	=	1519.0	nM	5.82	Activation of recombinant human AMPK alpha1/beta1/gamma1 using Cy5-labelled SAMS...	27490827

Literature References

PubMed	DOI	Target Context	# Activities
36518704	10.1021/acsmedchemlett.2c00196	HCT-116	8
19678707	10.1021/jm900728u	Unchecked	7
11754592	10.1021/jm010369e	P2Y purinoceptor 1	6
12459011	10.1021/jm0208370	Human immunodeficiency virus type 1 protease	4
4045916	10.1021/jm00148a002	Vesicular stomatitis virus	4
29723786	10.1016/j.ejmech.2018.04.045	Transient receptor potential cation channel subfamily M member 2	4
4045916	10.1021/jm00148a002	Coxsackievirus B4	4
8254622	10.1021/jm00076a023	Cavia porcellus	3
966249	10.1021/jm00230a011	Unchecked	3
25091927	10.1016/j.bmcl.2014.07.036	Adenylate kinase isoenzyme 1	3
671448	10.1021/jm00204a004	NON-PROTEIN TARGET	3
17603473	10.1038/nature05981	5-methylthioadenosine/S-adenosylhomocysteine deaminase	3
36518704	10.1021/acsmedchemlett.2c00196	Unchecked	3
16884311	10.1021/jm060490r	2-dehydropantoate 2-reductase	3
27490827	10.1021/acs.jmedchem.6b00866	NON-PROTEIN TARGET	3
21755941	10.1021/jm200650j	Adenosine deaminase-like protein	3
12672257	10.1021/jm011070z	Rattus norvegicus	3
22417091	10.1021/jm201734r	L-lactate dehydrogenase A chain	3
8254622	10.1021/jm00076a023	Oryctolagus cuniculus	3
27490827	10.1021/acs.jmedchem.6b00866	AMP-activated protein kinase (AMPK) alpha-1/beta-1/gamma-1	3

Data from ChEMBL 36 via Core Engine