Triphosphopyridine nucleotide

Details

• Internal ID: 58ab5820-8c1f-4508-968f-4ce19a999d17
• Taxonomy: Nucleosides, nucleotides, and analogues > (5->5)-dinucleotides
• IUPAC Name: [[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
• SMILES (Canonical): C1=CC(=C[N+](=C1)C2C(C(C(O2)COP(=O)([O-])OP(=O)(O)OCC3C(C(C(O3)N4C=NC5=C(N=CN=C54)N)OP(=O)(O)O)O)O)O)C(=O)N
• SMILES (Isomeric): C1=CC(=C[N+](=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)([O-])OP(=O)(O)OC[C@@H]3[C@H]([C@H]([C@@H](O3)N4C=NC5=C(N=CN=C54)N)OP(=O)(O)O)O)O)O)C(=O)N
• InChI: InChI=1S/C21H28N7O17P3/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(44-46(33,34)35)14(30)11(43-21)6-41-48(38,39)45-47(36,37)40-5-10-13(29)15(31)20(42-10)27-3-1-2-9(4-27)18(23)32/h1-4,7-8,10-11,13-16,20-21,29-31H,5-6H2,(H7-,22,23,24,25,32,33,34,35,36,37,38,39)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
• InChI Key: XJLXINKUBYWONI-NNYOXOHSSA-N
• Popularity: 33,852 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈N₇O₁₇P₃
• Molecular Weight: 743.40 g/mol
• Exact Mass: 743.07545344 g/mol
• Topological Polar Surface Area (TPSA): 368.00 Ų
• XlogP: -7.10
• Atomic LogP (AlogP): -3.53
• H-Bond Acceptor: 19
• H-Bond Donor: 8
• Rotatable Bonds: 13

Synonyms

• 53-59-8
• NADP
• coenzyme II
• Codehydrogenase II
• Cozymase II
• Codehydrase II
• TPN (nucleotide)
• NAD phosphate
• beta-NADP
• Nadide phosphate
• nicotinamide adenine dinucleotide phosphate
• beta-TPN
• beta-nicotinamide adenine dinucleotide phosphate
• Nicotinamide-adenine dinucleotide phosphate
• CHEBI:44409
• NADP zwitterion
• BRN 3885115
• Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'-5'-ester with 3-(aminocarbonyl)-1-beta-D-ribofuranosylpyridinium, inner salt
• Adenine-nicotinamide dinucleotide phosphate
• TPN-ox
• b-NADP
• Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), 5'->'-ester with 3-(aminocarbonyl)-1-beta-D-ribofuranosylpyridinium hydroxide, inner salt
• Pyridinium, 3-carbamoyl-1-beta-D-ribofuranosyl-, hydroxide, 5',5'-ester with adenosine 2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate), inner salt
• TPN+
• TPN
• 2'-MONOPHOSPHOADENOSINE 5'-DIPHOSPHORIBOSE
• nicotinamide adenine dinucleotide-P
• EINECS 200-178-1
• UNII-BY8P107XEP
• Codehydrogenaseii
• beta-Nicotinamide adenine dinucleotide phosphate hydrate
• .beta.-NADP
• b-TPN
• NADP+ (hydrate)
• SCHEMBL7869
• 4-26-00-03672 (Beilstein Handbook Reference)
• CHEMBL295069
• DTXSID50889327
• XJLXINKUBYWONI-NNYOXOHSSA-N
• Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-beta-D-ribofuranosylpyridinium, inner salt
• DB03461
• [[(2R,3R,4R,5R)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
• AC-37030
• Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'.fwdarw.5'-ester with 3-(aminocarbonyl)-1-.beta.-D-ribofuranosylpyridinium, inner salt
• BP-58609
• HY-113325
• b-Nicotinamide adenine dinucleotide phosphate
• CS-0059610
• D87726
• Q28747
• Beta -Nicotinamide adenine dinucleotide phosphate
• .beta.-Nicotinamide adenine dinucleotide phosphate
• W-203016
• 944A1E1D-E8B9-42AF-B61D-7C4242AB099A
• ss-Nicotinamide adenine dinucleotide phosphate hydrate, NAPD
• 1-((2R,3R,4S,5R)-5-((((((((2R,3R,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)tetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryl)oxy)oxidophosphoryl)oxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-3-carbamoylpyridin-1-ium
• 1-((2R,3R,4S,5R)-5-((((((2R,3R,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-hydroxy-4-(phosphonooxy)tetrahydrofuran-2-yl)methoxy)(hydroxy)phosphoryloxy)oxidophosphoryloxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-3-carbamoylpyridinium
• Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'->5'-ester with 3-(aminocarbonyl)-1-beta-D-ribofuranosylpyridinium, inner salt
• Adenosine 5'-(trihydrogen diphosphate), 2'-(dihydrogen phosphate), P'-5'-ester with 3-(aminocarbonyl)-1-beta-D-ribofuranosylpyridinium, inner salt (9CI)
• Pyridinium, 3-carbamoyl-1-beta-D-ribofuranosyl-, hydroxide, 5'-5'-ester with adenosine 2'-(dihydrogen phosphate) 5'-(trihydrogen pyrophosphate), inner salt (8CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6820	68.20%
Caco-2	-	0.8742	87.42%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.3954	39.54%
OATP2B1 inhibitior	+	0.5716	57.16%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6752	67.52%
P-glycoprotein inhibitior	+	0.7145	71.45%
P-glycoprotein substrate	+	0.6298	62.98%
CYP3A4 substrate	+	0.6760	67.60%
CYP2C9 substrate	-	0.8011	80.11%
CYP2D6 substrate	-	0.8708	87.08%
CYP3A4 inhibition	-	0.8838	88.38%
CYP2C9 inhibition	-	0.9148	91.48%
CYP2C19 inhibition	-	0.9027	90.27%
CYP2D6 inhibition	-	0.9136	91.36%
CYP1A2 inhibition	-	0.8820	88.20%
CYP2C8 inhibition	+	0.7233	72.33%
CYP inhibitory promiscuity	-	0.9353	93.53%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5237	52.37%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.9106	91.06%
Skin irritation	-	0.7634	76.34%
Skin corrosion	-	0.9263	92.63%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3594	35.94%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	-	0.5038	50.38%
skin sensitisation	-	0.8449	84.49%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.7746	77.46%
Acute Oral Toxicity (c)	III	0.4181	41.81%
Estrogen receptor binding	+	0.7513	75.13%
Androgen receptor binding	+	0.7224	72.24%
Thyroid receptor binding	+	0.5604	56.04%
Glucocorticoid receptor binding	+	0.6510	65.10%
Aromatase binding	+	0.6474	64.74%
PPAR gamma	+	0.7562	75.62%
Honey bee toxicity	-	0.7173	71.73%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.6432	64.32%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.18%	96.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	96.52%	80.33%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.67%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	90.77%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.47%	99.23%
CHEMBL3902	P09211	Glutathione S-transferase Pi	89.54%	93.81%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.30%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.43%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	87.03%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.95%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.39%	95.89%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	85.89%	95.48%
CHEMBL2535	P11166	Glucose transporter	82.77%	98.75%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.75%	95.83%
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	81.88%	88.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.79%	99.17%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	81.40%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.26%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.01%	96.95%
CHEMBL288	Q08499	Phosphodiesterase 4D	80.51%	97.50%
CHEMBL1741221	Q9Y4P1	Cysteine protease ATG4B	80.29%	87.50%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	80.24%	93.65%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 5885
• LOTUS: LTS0028089
• wikiData: Q71530982