3',5'-cyclic AMP(1-)

Details

• Internal ID: 57d2a4df-ba07-469f-a8c8-a14f47e964fa
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleotides > Cyclic purine nucleotides > 3,5-cyclic purine nucleotides
• IUPAC Name: (4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
• SMILES (Canonical): C1C2C(C(C(O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(O1)[O-]
• SMILES (Isomeric): C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(O1)[O-]
• InChI: InChI=1S/C10H12N5O6P/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)/p-1/t4-,6-,7-,10-/m1/s1
• InChI Key: IVOMOUWHDPKRLL-KQYNXXCUSA-M
• Popularity: 72,503 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₁N₅O₆P-
• Molecular Weight: 328.20 g/mol
• Exact Mass: 328.04469509 g/mol
• Topological Polar Surface Area (TPSA): 158.00 Ų
• XlogP: -2.60
• Atomic LogP (AlogP): -1.45
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• cyclic-AMP
• MLS001333136
• adenosine-3',5'-monophosphate
• adenosine cyclic-3',5'-monophosphate
• adenosine-3',5'-cyclic monophosphate
• cyclic-3',5'-adenosine monophosphate
• SMR000875274
• 3clp
• 3ocp
• 3otf
• 2k0g
• 3',5'-cyclic AMP anion
• BDBM81289
• CHEBI:58165
• 3u10
• cid_23669773
• DTXSID501214160
• NCGC00485221-01
• (4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
• adenosine 3',5'-cyclic monophosphate anion
• adenosine 3',5'-cyclic monophosphate(1-)
• A832959
• Q27125416
• Adenosine, cyclic 3',5'-(hydrogen phosphate), ion(1-)
• (1S,6R,8R,9R)-8-(6-aminopurin-9-yl)-3-hydroxy-3-oxo-2,4,7-trioxa-3?5-phosphabicyclo[4.3.0]nonan-9-ol
• (4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-oxidanidyl-2-oxidanylidene-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
• (4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphorin-7-ol
• 62906-31-4
• sodium;(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-oxidanidyl-2-oxidanylidene-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
• sodium;(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphorin-7-ol
• sodium;(4aR,6R,7R,7aS)-6-adenin-9-yl-2-keto-2-oxido-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphorin-7-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6936	69.36%
Caco-2	-	0.8727	87.27%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.3537	35.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9508	95.08%
OATP1B3 inhibitior	+	0.9439	94.39%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9626	96.26%
P-glycoprotein inhibitior	-	0.8586	85.86%
P-glycoprotein substrate	-	0.6216	62.16%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8694	86.94%
CYP3A4 inhibition	-	0.9446	94.46%
CYP2C9 inhibition	-	0.9380	93.80%
CYP2C19 inhibition	-	0.9229	92.29%
CYP2D6 inhibition	-	0.9347	93.47%
CYP1A2 inhibition	-	0.9035	90.35%
CYP2C8 inhibition	-	0.7528	75.28%
CYP inhibitory promiscuity	-	0.9644	96.44%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4589	45.89%
Eye corrosion	-	0.9855	98.55%
Eye irritation	-	0.9550	95.50%
Skin irritation	-	0.7711	77.11%
Skin corrosion	-	0.9308	93.08%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8699	86.99%
Micronuclear	+	0.9900	99.00%
Hepatotoxicity	+	0.6381	63.81%
skin sensitisation	-	0.8614	86.14%
Respiratory toxicity	+	0.9000	90.00%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6979	69.79%
Acute Oral Toxicity (c)	III	0.5411	54.11%
Estrogen receptor binding	+	0.6462	64.62%
Androgen receptor binding	-	0.7933	79.33%
Thyroid receptor binding	+	0.5989	59.89%
Glucocorticoid receptor binding	-	0.8662	86.62%
Aromatase binding	+	0.6849	68.49%
PPAR gamma	+	0.6211	62.11%
Honey bee toxicity	-	0.8285	82.85%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	-	0.5828	58.28%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	98.11%	95.48%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	96.74%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	96.71%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.39%	96.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	91.44%	80.33%
CHEMBL3589	P55263	Adenosine kinase	89.92%	98.05%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.17%	91.11%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.14%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.89%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.77%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.63%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	86.27%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.95%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.82%	86.33%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	82.54%	98.46%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.65%	82.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.21%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.31%	97.36%

Plants that contains it

• Ziziphus jujuba

Cross-Links

• PubChem: 7059571
• NPASS: NPC212549