(4aR,6S,7S,7aR)-6-(6-aminopurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol

Details

• Internal ID: 0d780a21-47c8-40be-b362-00e5f7f91370
• Taxonomy: Nucleosides, nucleotides, and analogues > Purine nucleotides > Cyclic purine nucleotides > 3,5-cyclic purine nucleotides
• IUPAC Name: (4aR,6S,7S,7aR)-6-(6-aminopurin-9-yl)-2-hydroxy-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)/t4-,6+,7+,10+/m1/s1
• InChI Key: IVOMOUWHDPKRLL-ASCDQALMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂N₅O₆P
• Molecular Weight: 329.21 g/mol
• Exact Mass: 329.05252012 g/mol
• Topological Polar Surface Area (TPSA): 155.00 Ų
• XlogP: -2.60
• Atomic LogP (AlogP): -0.82
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

• CHEBI:181694
• Q63408961
• (4aR,6S,7S,7aR)-6-(6-aminopurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol
• (4aR,6S,7S,7aR)-6-(6-aminopurin-9-yl)-2-hydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-uro[3,2-d][1,3,2]dioxaphosphinin-7-ol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8142	81.42%
Caco-2	-	0.8727	87.27%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.4051	40.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9507	95.07%
OATP1B3 inhibitior	+	0.9449	94.49%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9626	96.26%
P-glycoprotein inhibitior	-	0.8586	85.86%
P-glycoprotein substrate	-	0.6248	62.48%
CYP3A4 substrate	+	0.5130	51.30%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8647	86.47%
CYP3A4 inhibition	-	0.9146	91.46%
CYP2C9 inhibition	-	0.9169	91.69%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9295	92.95%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.7541	75.41%
CYP inhibitory promiscuity	-	0.9319	93.19%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5090	50.90%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.9550	95.50%
Skin irritation	-	0.7679	76.79%
Skin corrosion	-	0.9293	92.93%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8699	86.99%
Micronuclear	+	0.9900	99.00%
Hepatotoxicity	-	0.5103	51.03%
skin sensitisation	-	0.8571	85.71%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.7142	71.42%
Acute Oral Toxicity (c)	III	0.5080	50.80%
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	-	0.8097	80.97%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	-	0.5706	57.06%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	3.5 nM	Potency	via Super-PRED
CHEMBL1293299	Q03164	Histone-lysine N-methyltransferase MLL	125.9 nM	Potency	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	251.2 nM; 5 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	200 nM	EC50	via Super-PRED
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	0.6 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3137261	O14744	PRMT5/MEP50 complex	97.45%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.66%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.54%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.27%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.57%	95.56%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	88.44%	80.33%
CHEMBL3589	P55263	Adenosine kinase	88.18%	98.05%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.11%	95.89%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	87.03%	98.46%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.44%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.42%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.78%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	82.93%	94.73%
CHEMBL2535	P11166	Glucose transporter	81.35%	98.75%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.12%	97.36%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.74%	93.10%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.02%	82.50%

Plants that contains it

• Isodon rubescens
• Ziziphus jujuba

Cross-Links

• PubChem: 25322948
• NPASS: NPC303729