1,4-Dihydronicotinamide adenine dinucleotide

Details

• Internal ID: 93fdfa4d-8995-4567-b0c1-b0744aa03cdc
• Taxonomy: Nucleosides, nucleotides, and analogues > (5->5)-dinucleotides
• IUPAC Name: [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
• SMILES (Canonical): C1C=CN(C=C1C(=O)N)C2C(C(C(O2)COP(=O)(O)OP(=O)(O)OCC3C(C(C(O3)N4C=NC5=C(N=CN=C54)N)O)O)O)O
• SMILES (Isomeric): C1C=CN(C=C1C(=O)N)[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)O)O)O)O
• InChI: InChI=1S/C21H29N7O14P2/c22-17-12-19(25-7-24-17)28(8-26-12)21-16(32)14(30)11(41-21)6-39-44(36,37)42-43(34,35)38-5-10-13(29)15(31)20(40-10)27-3-1-2-9(4-27)18(23)33/h1,3-4,7-8,10-11,13-16,20-21,29-32H,2,5-6H2,(H2,23,33)(H,34,35)(H,36,37)(H2,22,24,25)/t10-,11-,13-,14-,15-,16-,20-,21-/m1/s1
• InChI Key: BOPGDPNILDQYTO-NNYOXOHSSA-N
• Popularity: 64,971 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₉N₇O₁₄P₂
• Molecular Weight: 665.40 g/mol
• Exact Mass: 665.12477262 g/mol
• Topological Polar Surface Area (TPSA): 318.00 Ų
• XlogP: -5.70
• Atomic LogP (AlogP): -2.69
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

• DPNH
• 58-68-4
• beta-DPNH
• beta-NADH
• 1,4-Dihydronicotinamide adenine dinucleotide
• Dihydrocozymase
• Coenzyme I, reduced
• Cozymase I, reduced
• NADH2
• dihydronicotinamide adenine dinucleotide
• Dihydrocodehydrogenase I
• Reduced codehydrogenase I
• Reduced nicotinamide adenine diphosphate
• Codehydrase I, reduced
• Dihydronicotinamide mononucleotide
• Reduced nicotinamide-adenine dinucleotide
• Codehydrogenase I, reduced
• Reduced diphosphopyridine nucleotide
• NAD reduced form
• Reduced Nicotinamide Adenine Dinucleotide
• [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl hydrogen phosphate
• CHEBI:16908
• Dihydronicotinamide-adenine dinucleotide
• 4J24DQ0916
• Nicotinamide-adenine dinucleotide, reduced
• nicotinamide adenine dinucleotide (reduced)
• Adenosine 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide
• Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with 1,4-dihydro-1beta-D-ribofuranosylnicotinamide
• nadh hydride
• coenzyme-I
• b-dpnh
• UNII-4J24DQ0916
• EINECS 200-393-0
• ENADA
• b-NADH
• Nicotinamide - adenine dinucleotide, reduced
• NADH [WHO-DD]
• bmse000054
• SCHEMBL8187
• NAD REDUCED FORM [MI]
• GTPL4487
• CHEMBL1234616
• DTXSID30889320
• BOPGDPNILDQYTO-NNYOXOHSSA-N
• DB00157
• [(2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-[[(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-phosphinic acid
• Adenosine 5'-(trihydrogen diphosphate), P'->5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide (9CI)
• Adenosine 5'-(trihydrogen pyrophosphate), 5'->5'-ester with 1,4-dihydro-1-beta-D-ribofuranosylnicotinamide (8CI)
• adenosine 5'-{3-[1-(3-carbamoyl-1,4-dihydropyridin-1-yl)-1,4-anhydro-D-ribitol-5-yl] dihydrogen diphosphate}
• Adenosine pyrophosphate, 5'->5'-ester with 1,4-dihydro-1-beta-D-ribofuranosylnicotinamide (7CI)
• C00004
• EN300-19742425
• Q26987453
• ((2R,3S,4R,5R)-5-(6-Aminopurin-9-yl)-3,4-dihydroxy-oxolan-2-yl)methoxy-((((2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxy-oxolan-2-yl)methoxy)hydroxyphosphoryl)oxyphosphinic acid
• [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4R,5R)-5-(3-carbamoyl-1,4-dihydropyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid
• [(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl [[(2R,3S,4R,5R)-5-(3-carbamoyl-4H-pyridin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] hydrogen phosphate
• Adenosine 5'-(trihydrogen diphosphate), 5'->'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide
• Adenosine 5'-(trihydrogen diphosphate), P'-->5'-ester with 1,4-dihydro-1-.beta.-D-ribofuranosyl-3-pyridinecarboxamide
• ADENOSINE 5'-(TRIHYDROGEN DIPHOSPHATE), P'->5'-ESTER WITH 1,4-DIHYDRO-1-.BETA.-D-RIBOFURANOSYL-3-PYRIDINECARBOXAMIDE
• Adenosine 5'-(trihydrogen diphosphate), P'->5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide
• Adenosine 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with 1,4-dihydro-1-beta-D-ribofuranosyl-3-pyridinecarboxamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5835	58.35%
Caco-2	-	0.8760	87.60%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.3957	39.57%
OATP2B1 inhibitior	-	0.7144	71.44%
OATP1B1 inhibitior	+	0.9297	92.97%
OATP1B3 inhibitior	+	0.9433	94.33%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	+	0.5927	59.27%
P-glycoprotein inhibitior	+	0.6919	69.19%
P-glycoprotein substrate	-	0.5000	50.00%
CYP3A4 substrate	+	0.6127	61.27%
CYP2C9 substrate	-	0.6050	60.50%
CYP2D6 substrate	-	0.8619	86.19%
CYP3A4 inhibition	-	0.8753	87.53%
CYP2C9 inhibition	-	0.8490	84.90%
CYP2C19 inhibition	-	0.8294	82.94%
CYP2D6 inhibition	-	0.8849	88.49%
CYP1A2 inhibition	-	0.7565	75.65%
CYP2C8 inhibition	+	0.5086	50.86%
CYP inhibitory promiscuity	-	0.8373	83.73%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.5192	51.92%
Eye corrosion	-	0.9841	98.41%
Eye irritation	-	0.9183	91.83%
Skin irritation	-	0.7602	76.02%
Skin corrosion	-	0.9210	92.10%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6484	64.84%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	-	0.5236	52.36%
skin sensitisation	-	0.8383	83.83%
Respiratory toxicity	+	0.9333	93.33%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.7418	74.18%
Acute Oral Toxicity (c)	III	0.4695	46.95%
Estrogen receptor binding	+	0.7191	71.91%
Androgen receptor binding	+	0.7378	73.78%
Thyroid receptor binding	+	0.5313	53.13%
Glucocorticoid receptor binding	+	0.6133	61.33%
Aromatase binding	+	0.6694	66.94%
PPAR gamma	+	0.7305	73.05%
Honey bee toxicity	-	0.7548	75.48%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8234	82.34%

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	99.38%	96.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	98.32%	80.33%
CHEMBL2243	O00519	Anandamide amidohydrolase	97.17%	97.53%
CHEMBL4040	P28482	MAP kinase ERK2	96.98%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.43%	91.11%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	93.45%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.98%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.94%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	88.81%	94.73%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	87.98%	95.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.21%	97.36%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.15%	99.23%
CHEMBL3891	P07384	Calpain 1	84.59%	93.04%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	84.44%	95.48%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.27%	99.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.50%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.09%	86.33%
CHEMBL1293294	P51151	Ras-related protein Rab-9A	82.50%	87.67%
CHEMBL5957	P21589	5'-nucleotidase	82.46%	97.78%
CHEMBL221	P23219	Cyclooxygenase-1	82.16%	90.17%
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	81.56%	82.86%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.51%	89.00%
CHEMBL2535	P11166	Glucose transporter	81.18%	98.75%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	81.00%	96.67%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.54%	94.33%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.41%	82.50%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 439153
• LOTUS: LTS0116908
• wikiData: Q26987453