Adenosine Phosphate

Details

• Internal ID: 85b57971-0dcd-4f78-ad31-b185da0854f4
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleotides > Purine ribonucleotides > Purine ribonucleoside monophosphates
• IUPAC Name: [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• SMILES (Canonical): C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)O)O)O)N
• SMILES (Isomeric): C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)O)O)O)N
• InChI: InChI=1S/C10H14N5O7P/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(22-10)1-21-23(18,19)20/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)/t4-,6-,7-,10-/m1/s1
• InChI Key: UDMBCSSLTHHNCD-KQYNXXCUSA-N
• Popularity: 39,412 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄N₅O₇P
• Molecular Weight: 347.22 g/mol
• Exact Mass: 347.06308480 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: -3.50
• Atomic LogP (AlogP): -1.86
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• 5'-adenylic acid
• adenosine phosphate
• Adenosine monophosphate
• 61-19-8
• adenylic acid
• adenosine 5'-phosphate
• 5'-AMP
• adenylate
• Phosphentaside
• Adenovite
• Phosphaden
• Cardiomone
• Phosaden
• Lycedan
• AMP
• Adenosine-5'-monophosphate
• Vitamin B8
• My-B-Den
• Myoston
• Monophosphadenine
• 5'-adenosine monophosphate
• Muskeladenylsaeure
• AMP (nucleotide)
• Ergadenylic acid
• Muscle adenylic acid
• a-5mp
• Adenosine 5'-(dihydrogen phosphate)
• Adenyl
• Fosfato de adenosina
• Adenosine-5'-monophosphoric acid
• Adenosine 5'-phosphoric acid
• Phosphate d'adenosine
• PAdo
• adenosine-monophosphate
• Adenosini phosphas
• adenosine-5'P
• Adenosine-5-monophosphoric acid
• Muskeladenosin-phosphorsaeure
• Adenylic acid (VAN)
• Ado5'P
• Adenosine 5'-monophosphoric acid
• adenosine-phosphate
• 5'-O-phosphonoadenosine
• A5MP
• AMP (VAN)
• NSC-20264
• Adenosini phosphas [INN-Latin]
• Adenosine, mono(dihydrogen phosphate) (ester)
• HSDB 3281
• A 5MP
• Fosfato de adenosina [INN-Spanish]
• Phosphate d'adenosine [INN-French]
• Adenosine-5-phosphate
• Formycin 5'-phosphate
• CHEBI:16027
• BRN 0054612
• 7gpb
• 8gpb
• EINECS 200-500-0
• Adenosine phosphate [USAN:INN:BAN]
• NSC 20264
• Formycin 5'-phosphate hydrate
• UNII-415SHH325A
• Adenyl (TN)
• ASMP
• [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
• DTXSID5022560
• Formycin 5'-monophosphate hydrate
• 415SHH325A
• Adenosine5'-monophosphate
• Formycin A 5'-monophosphate hydrate
• Adenosine phosphate [USAN:BAN:INN]
• Adenosine 5' monophosphate
• CHEMBL752
• 5'-Thio-5'-adenylic acid
• Adenosine Monophosphate (Amp)
• {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
• ADENOSINE-5'-PHOSPHATE
• DTXCID002560
• Adenosine 5-Monophosphate
• ((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl dihydrogen phosphate
• Adenosine phosphate (USAN/INN)
• 8-Aminoadenosine 5'-monophosphate
• 4-26-00-03615 (Beilstein Handbook Reference)
• 67583-85-1
• AMP dianion
• NCGC00163319-01
• NCGC00163319-03
• 5'-Deoxy-5'-thioadenosine 5'-monophosphate
• ADENOSINE 5'-(DIHYDROGEN PHOSPHATE).
• 7-Amino-3-beta-D-ribofuranosyl-1H-pyrazolo(4,3-d)pyrimidine 5'-(dihydrogen phosphate) hydrate
• 136920-07-5
• 122768-03-0
• Adenosini phosphas (INN-Latin)
• 5'-O-phosphonatoadenosine
• 7A8E6D15-9136-44C1-88C9-E1A224638E56
• ADENOSINE PHOSPHATE (MART.)
• ADENOSINE PHOSPHATE [MART.]
• NSC20264
• 5'-ADENYLIC ACID (USP-RS)
• 5'-ADENYLIC ACID [USP-RS]
• Adenosine-5'-Monophosphate, Free acid
• Adenosine-5-monophosphate(2-)
• CAS-61-19-8
• Adenosine-5-monophosphate dianion
• (S)-1-C-(7-Amino-1H-pyrazolo(4,3-d)pyrimidin-3-yl)-1,4-anhydro-D-ribitol, 5-(dihydrogen phosphate)
• 1H-Pyrazolo(4,3-d)pyrimidine, 7-amino-3-beta-D-ribofuranosyl-, 5'-(dihydrogen phosphate)-, hydrate
• adenosin-5'-monophosphat
• Adenosine 5' Phosphate
• 5'-Phosphate, Adenosine
• Adenosine 5 -monophosphate
• Muscle adenylate
• adenosina fosfato
• adenosinphosphat-
• MFCD00005750
• 5'adenylic acid
• Adenosine 5'-monophosphate, free acid
• 1pyg
• 2gsu
• 5'-adenylate
• My-beta-Den
• 24937-83-5
• T-ADENYLIC
• 1ua4
• 1z6s
• adenosine 5'-phosphates
• Adenosin-5-monophosphate
• Adenosine 5'-phosphorate
• Prestwick0_000356
• Prestwick1_000356
• Prestwick2_000356
• Prestwick3_000356
• bmse000005
• bmse000873
• bmse000992
• D06ACW
• Epitope ID:137353
• Adenosine-5-monophosphorate
• SCHEMBL5588
• 5-AMP
• Adenosine-5'-monophosphorate
• adenosine-5'-phosphoric acid
• BSPBio_000451
• SPBio_002372
• BPBio1_000497
• GTPL2455
• [3h]adenosine 5'-monophosphate
• Adenosine phosphate(Vitamin B8)
• C10H14N5O7P.H2O
• SCHEMBL18287224
• 5'-ADENYLIC ACID [MI]
• BDBM18137
• CHEBI:22256
• CHEBI:37096
• 5'-ADENYLIC ACID [FCC]
• ADENOSINE PHOSPHATE [INN]
• C01EB10
• [(2R,3S,4R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-2-oxolanyl]methyl dihydrogen phosphate
• ADENOSINE PHOSPHATE [HSDB]
• ADENOSINE PHOSPHATE [INCI]
• ADENOSINE PHOSPHATE [USAN]
• ADENOSINE PHOSPHATE [VANDF]
• AMY30021
• HY-A0181
• Tox21_112046
• ADENOSINE PHOSPHATE [WHO-DD]
• s9366
• AKOS015833068
• AKOS015888563
• Tox21_112046_1
• CCG-267996
• DB00131
• Adenosine 5\'-monophosphate monohydrate
• NCGC00163319-02
• [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate
• AS-11783
• BP-58695
• C10-H14-N5-O7-P.H2-O
• LS-129209
• A0158
• CS-0017523
• Adenosine 5'-Monophosphate (5'-Adenylic Acid)
• C00020
• D02769
• F20323
• EN300-1700412
• Adenosine-3(+2')-monophosphoric acid monohydrate*
• Q318369
• J-700145
• W-105182
• Adenosine 5'-monophosphate-Agarose, lyophilized powder
• Adenosine 5'-monophosphate-Agarose, saline suspension
• Z2216887941
• 9H-Purin-6-amine, 9-(5-O-phosphono-.beta.-D-ribofuranosyl)-
• 9H-purin-6-amine, 9-(5-O-phosphono-beta-D-ribofuranosyl)-
• [(2R,3S,4R,5R)-5-adenin-9-yl-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl dihydrogen phosphate;hydrate
• 53624-78-5
• Adenosine 5'-monophosphate-Agarose, lyophilized powder, Contains lactose stabilizers that must be removed prior to use.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4885	48.85%
Caco-2	-	0.9203	92.03%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4045	40.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9575	95.75%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9164	91.64%
P-glycoprotein inhibitior	-	0.8621	86.21%
P-glycoprotein substrate	-	0.8584	85.84%
CYP3A4 substrate	-	0.5092	50.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8648	86.48%
CYP3A4 inhibition	-	0.9296	92.96%
CYP2C9 inhibition	-	0.9419	94.19%
CYP2C19 inhibition	-	0.9293	92.93%
CYP2D6 inhibition	-	0.9210	92.10%
CYP1A2 inhibition	-	0.9078	90.78%
CYP2C8 inhibition	-	0.8010	80.10%
CYP inhibitory promiscuity	-	0.9633	96.33%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5557	55.57%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9610	96.10%
Skin irritation	-	0.7589	75.89%
Skin corrosion	-	0.9254	92.54%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7483	74.83%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	-	0.5486	54.86%
skin sensitisation	-	0.8414	84.14%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8449	84.49%
Acute Oral Toxicity (c)	III	0.4907	49.07%
Estrogen receptor binding	+	0.5944	59.44%
Androgen receptor binding	+	0.5601	56.01%
Thyroid receptor binding	+	0.6201	62.01%
Glucocorticoid receptor binding	-	0.4750	47.50%
Aromatase binding	+	0.8403	84.03%
PPAR gamma	+	0.5543	55.43%
Honey bee toxicity	-	0.7807	78.07%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.6308	63.08%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL226	P30542	Adenosine A1 receptor	500 nM; 500 nM	EC50; EC50	PMID: 22738238; via Super-PRED
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	800 nM; 1000 nM; 440 nM; 140 nM; 1000 nM; 140 nM	IC50; IC50; IC50; IC50; IC50; IC50	PMID: 11140724; PMID: 19348494; PMID: 19969452; PMID: 19969452; DOI: 10.1039/C0MD00269K; via Super-PRED
CHEMBL4315	P47900	Purinergic receptor P2Y1	1500 nM; 7200 nM	EC50; EC50	PMID: 11754592; PMID: 11754592
CHEMBL4398	P41231	Purinergic receptor P2Y2	85 nM; 3700 nM	EC50; EC50	PMID: 11754592; PMID: 11754592
CHEMBL1293232	Q16637	Survival motor neuron protein	31622.8 nM	Potency	via CMAUP
CHEMBL267	P12931	Tyrosine-protein kinase SRC	100 nM	IC50	PMID: 1479375

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.49%	96.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	97.75%	80.33%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	94.42%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	91.27%	94.73%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	88.62%	94.01%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.15%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.47%	95.89%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	83.05%	95.48%
CHEMBL5957	P21589	5'-nucleotidase	82.96%	97.78%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	82.13%	91.11%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	82.03%	96.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.75%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.55%	99.23%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.16%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.34%	99.17%

Plants that contains it

• Arabidopsis thaliana
• Helianthus tuberosus
• Isodon rubescens
• Populus tremula

Cross-Links

• PubChem: 6083
• NPASS: NPC185991
• ChEMBL: CHEMBL752
• LOTUS: LTS0007212
• wikiData: Q318369