cyclic ADP-ribose

Details

• Internal ID: 90028159-e907-407c-b412-7ae4cad988cb
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Monosaccharides > Pentoses > Pentose phosphates
• IUPAC Name: (2R,3R,4S,5R,13R,14S,15R,16R)-8,10-dihydroxy-24-imino-8,10-dioxo-7,9,11,25,26-pentaoxa-1,17,19,22-tetraza-8lambda5,10lambda5-diphosphapentacyclo[18.3.1.12,5.113,16.017,21]hexacosa-18,20,22-triene-3,4,14,15-tetrol
• SMILES (Canonical): C1C2C(C(C(O2)N3C=NC4=C3N=CN(C4=N)C5C(C(C(O5)COP(=O)(OP(=O)(O1)O)O)O)O)O)O
• SMILES (Isomeric): C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C3N=CN(C4=N)[C@H]5[C@@H]([C@@H]([C@H](O5)COP(=O)(OP(=O)(O1)O)O)O)O)O)O
• InChI: InChI=1S/C15H21N5O13P2/c16-12-7-13-18-4-19(12)14-10(23)8(21)5(31-14)1-29-34(25,26)33-35(27,28)30-2-6-9(22)11(24)15(32-6)20(13)3-17-7/h3-6,8-11,14-16,21-24H,1-2H2,(H,25,26)(H,27,28)/t5-,6-,8-,9-,10-,11-,14-,15-/m1/s1
• InChI Key: BQOHYSXSASDCEA-KEOHHSTQSA-N
• Popularity: 766 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₁N₅O₁₃P₂
• Molecular Weight: 541.30 g/mol
• Exact Mass: 541.06110974 g/mol
• Topological Polar Surface Area (TPSA): 259.00 Ų
• XlogP: -5.70
• Atomic LogP (AlogP): -2.79
• H-Bond Acceptor: 16
• H-Bond Donor: 7
• Rotatable Bonds: 0

Synonyms

• cADPR
• 119340-53-3
• cAPD ribose
• E-NAD
• Cyclic ADP-?ribose
• cyclic ADP-D-ribose
• Cyclic Adenosine Diphosphate Ribose
• cADP-Ribose (cADPR)
• Q780BR06V8
• (2R,3R,4S,5R,13R,14S,15R,16R)-8,10-dihydroxy-24-imino-8,10-dioxo-7,9,11,25,26-pentaoxa-1,17,19,22-tetraza-8lambda5,10lambda5-diphosphapentacyclo[18.3.1.12,5.113,16.017,21]hexacosa-18,20,22-triene-3,4,14,15-tetrol
• Cyclic ADP Ribose
• Cyclic adenosine 5'-diphosphate ribose ammonium salt
• Adenosine 5'-(trihydrogen diphosphate), N-alpha-D-ribofuranosyl-, intramol. 5'-5'-ester
• UNII-Q780BR06V8
• GTPL2445
• SCHEMBL21437128
• CHEBI:31445
• DTXSID50896995
• BQOHYSXSASDCEA-KEOHHSTQSA-N
• HY-N7395
• AKOS040744206
• CS-0119339
• J-004109
• Q2467043
• Q27459000
• (2R,3R,4S,5R,13R,14S,15R,16R)-3,4,8,10,14,15-hexahydroxy-24-imino-7,9,11,25,26-pentaoxa-1,17,19,22-tetraaza-8$l^{5},10$l^{5}-diphosphapentacyclo[18.3.1.1^{2,5}.1^{13,16}.0^{17,21}]hexacosa-18,20,22-triene-8,10-dione
• (2R,3R,4S,5R,8S,10R,13R,14S,15R,16R,24E)-24-imino-7,9,11,25,26-pentaoxa-1,17,19,22-tetraaza-8,10-diphosphapentacyclo[18.3.1.1~2,5~.1~13,16~.0~17,21~]hexacosa-18,20,22-triene-3,4,8,10,14,15-hexol 8,10-dioxide (non-preferred name)
• ADENOSINE 5'-(TRIHYDROGEN DIPHOSPHATE), N-.ALPHA.-D-RIBOFURANOSYL-, INTRAMOL. 5'-5'-ESTER

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6661	66.61%
Caco-2	-	0.8756	87.56%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.3881	38.81%
OATP2B1 inhibitior	-	0.8584	85.84%
OATP1B1 inhibitior	+	0.9548	95.48%
OATP1B3 inhibitior	+	0.9434	94.34%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.4868	48.68%
P-glycoprotein inhibitior	-	0.4587	45.87%
P-glycoprotein substrate	-	0.6870	68.70%
CYP3A4 substrate	+	0.5209	52.09%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8675	86.75%
CYP3A4 inhibition	-	0.9607	96.07%
CYP2C9 inhibition	-	0.9029	90.29%
CYP2C19 inhibition	-	0.8876	88.76%
CYP2D6 inhibition	-	0.9070	90.70%
CYP1A2 inhibition	-	0.8178	81.78%
CYP2C8 inhibition	-	0.8085	80.85%
CYP inhibitory promiscuity	-	0.9756	97.56%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.5994	59.94%
Eye corrosion	-	0.9838	98.38%
Eye irritation	-	0.9395	93.95%
Skin irritation	-	0.7593	75.93%
Skin corrosion	-	0.9254	92.54%
Ames mutagenesis	-	0.5154	51.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.4586	45.86%
Micronuclear	+	0.9700	97.00%
Hepatotoxicity	+	0.5630	56.30%
skin sensitisation	-	0.8410	84.10%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.5616	56.16%
Acute Oral Toxicity (c)	III	0.5297	52.97%
Estrogen receptor binding	+	0.7043	70.43%
Androgen receptor binding	+	0.7364	73.64%
Thyroid receptor binding	+	0.5505	55.05%
Glucocorticoid receptor binding	-	0.5567	55.67%
Aromatase binding	+	0.7128	71.28%
PPAR gamma	+	0.6539	65.39%
Honey bee toxicity	-	0.7857	78.57%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.5708	57.08%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	97.30%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.64%	96.09%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	92.91%	95.48%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	89.98%	80.33%
CHEMBL3401	O75469	Pregnane X receptor	88.36%	94.73%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	87.38%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.48%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.04%	99.23%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	85.67%	98.46%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.99%	89.00%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	82.35%	93.65%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.14%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.00%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.90%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.63%	100.00%
CHEMBL3038469	P24941	CDK2/Cyclin A	80.39%	91.38%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 123847
• LOTUS: LTS0252818
• wikiData: Q2467043