Flavin Adenine Dinucleotide

Details

• Internal ID: 296634ce-d283-4eea-9544-2d154f96527a
• Taxonomy: Nucleosides, nucleotides, and analogues > Flavin nucleotides
• IUPAC Name: [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] hydrogen phosphate
• InChI: InChI=1S/C27H33N9O15P2/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43)/t14-,15+,16+,19-,20+,21+,26+/m0/s1
• InChI Key: VWWQXMAJTJZDQX-UYBVJOGSSA-N
• Popularity: 6,395 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₃N₉O₁₅P₂
• Molecular Weight: 785.50 g/mol
• Exact Mass: 785.15713538 g/mol
• Topological Polar Surface Area (TPSA): 356.00 Ų
• XlogP: -5.00
• Atomic LogP (AlogP): -2.42
• H-Bond Acceptor: 21
• H-Bond Donor: 9
• Rotatable Bonds: 13

Synonyms

• 146-14-5
• Flavin-adenine dinucleotide
• Flavine-adenine dinucleotide
• FAD
• Flavine adenosine diphosphate
• Adenine-riboflavin dinucleotide
• Riboflavin 5'-adenosine diphosphate
• flavitan
• Flavin adenin dinucleotide
• Adenine-flavin dinucleotide
• Adenine-flavine dinucleotide
• Flavine adenine dinucleotide
• Riboflavin-adenine dinucleotide
• Adenine-riboflavine dinucleotide
• Riboflavine-adenine dinucleotide
• Flanin F
• Isoalloxazine-adenine dinucleotide
• Flavinat
• Flamitajin B
• ZC44YTI8KK
• Flaziren (free acid)
• CHEBI:16238
• Adenine-riboflavin dinuceotide
• NSC-112207
• [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxobenzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl] hydrogen phosphate
• Riboflavin 5'-(trihydrogen diphosphate), 5'-5'-ester with adenosine
• Riboflavin 5'-(trihydrogen diphosphate), P'-5'-ester with adenosine
• ADENOSINE 5'-(TRIHYDROGEN PYROPHOSPHATE), 5'-5'-ESTER with RIBOFLAVINE
• Riboflavin 5'-(trihydrogen diphosphate), P'.fwdarw.5'-ester with adenosine
• 1H-Purin-6-amine, flavin dinucleotide
• 1H-Purin-6-amine, flavine dinucleotide
• adenosine 5'-[3-(riboflavin-5'-yl) dihydrogen diphosphate]
• Riboflavin 5'-(trihydrogen diphosphate), P'->5'-ester with adenosine
• BRN 0078150
• (((2R,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl)methoxy)(((((2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl)-2,3,4-trihydroxypentyl)oxy)(hydroxy)phosphoryl)oxy)phosphinic acid
• {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}[({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid
• UNII-ZC44YTI8KK
• Flamitajin
• FAD; NSC 112207
• Fademin
• Flaziren
• Adeflavin (TN)
• EINECS 205-663-1
• Flavinadenindinucleotid
• NSC 112207
• MFCD00041835
• flavin-adenine-dinucleotide
• 4-26-00-03632 (Beilstein Handbook Reference)
• SCHEMBL505095
• FLAVINADENINEDINUCLEOTIDE
• GTPL5184
• CHEMBL1232653
• DTXSID4048307
• VWWQXMAJTJZDQX-UYBVJOGSSA-N
• Flavin adenine dinucleotide (JAN)
• 1H-Purin-6-amine flavin dinucleotide
• 1H-Purin-6-amine flavine dinucleotide
• AKOS015915279
• DB03147
• FLAVIN-ADENINE DINUCLEOTIDE [MI]
• FLAVINE ADENINE DINUCLEOTIDE [WHO-DD]
• C00016
• D00005
• F87829
• Q28746
• EN300-19733360
• 3-HYDROXY-1H-INDOLE-2-CARBOXYLICACIDETHYLESTER
• Riboflavine, 5'-ester with adenosine 5'-diphosphate (8CI)
• Adenosine 5'-(trihydrogen pyrophosphate), 5'-5'-ester with riboflavine (8CI)
• RIBOFLAVINE 5'-(TRIHYDROGEN DIPHOSPHATE) 5'->5'-ESTER WITH ADENOSINE
• [({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4S)-5-{7,8-dimethyl-2,4-dioxo-2H,3H,4H,10H-benzo[g]pteridin-10-yl}-2,3,4-trihydroxypentyl]oxy})phosphinic acid
• [(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3S,4S)-5-(7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl)-2,3,4-trihydroxypentyl dihydrogen diphosphate (non-preferred name)
• adenosine 5'-(3-{D-ribo-5-[7,8-dimethyl-2,4-dioxo-3,4-dihydrobenzo[g]pteridin-10(2H)-yl]-2,3,4-trihydroxypentyl} dihydrogen diphosphate)
• Flavinadeninedinucleotide,riboflavinsquare5'-adenosinesquarediphosphate,adenineflavindinucleotide,isoalloxazinesquareadeninedinucleotide,fad

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7518	75.18%
Caco-2	-	0.8634	86.34%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.3623	36.23%
OATP2B1 inhibitior	-	0.7132	71.32%
OATP1B1 inhibitior	+	0.8806	88.06%
OATP1B3 inhibitior	+	0.9387	93.87%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8641	86.41%
P-glycoprotein inhibitior	+	0.7380	73.80%
P-glycoprotein substrate	+	0.6914	69.14%
CYP3A4 substrate	+	0.6936	69.36%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8734	87.34%
CYP3A4 inhibition	-	0.7323	73.23%
CYP2C9 inhibition	-	0.8818	88.18%
CYP2C19 inhibition	-	0.8720	87.20%
CYP2D6 inhibition	-	0.8636	86.36%
CYP1A2 inhibition	-	0.8426	84.26%
CYP2C8 inhibition	+	0.6756	67.56%
CYP inhibitory promiscuity	-	0.8967	89.67%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8500	85.00%
Carcinogenicity (trinary)	Non-required	0.5475	54.75%
Eye corrosion	-	0.9849	98.49%
Eye irritation	-	0.9106	91.06%
Skin irritation	-	0.7775	77.75%
Skin corrosion	-	0.9306	93.06%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3827	38.27%
Micronuclear	+	0.9900	99.00%
Hepatotoxicity	-	0.6307	63.07%
skin sensitisation	-	0.8583	85.83%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.9250	92.50%
Acute Oral Toxicity (c)	III	0.5359	53.59%
Estrogen receptor binding	+	0.7960	79.60%
Androgen receptor binding	+	0.7625	76.25%
Thyroid receptor binding	+	0.6116	61.16%
Glucocorticoid receptor binding	+	0.7011	70.11%
Aromatase binding	+	0.8686	86.86%
PPAR gamma	+	0.7377	73.77%
Honey bee toxicity	-	0.6899	68.99%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.7433	74.33%

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	99.03%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.85%	96.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	98.85%	80.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	95.54%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	95.20%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.38%	89.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	92.60%	93.10%
CHEMBL2581	P07339	Cathepsin D	92.23%	98.95%
CHEMBL235	P37231	Peroxisome proliferator-activated receptor gamma	92.21%	95.39%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.48%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.27%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.17%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.64%	99.17%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	89.23%	100.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.52%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.25%	95.56%
CHEMBL2243	O00519	Anandamide amidohydrolase	88.23%	97.53%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	88.13%	100.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.34%	93.40%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	87.03%	93.04%
CHEMBL2535	P11166	Glucose transporter	86.20%	98.75%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	85.65%	93.65%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.67%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.49%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	83.47%	94.75%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.39%	90.71%
CHEMBL4581	P52732	Kinesin-like protein 1	81.77%	93.18%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	81.57%	98.33%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	81.03%	96.67%
CHEMBL290	Q13370	Phosphodiesterase 3B	80.63%	94.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.59%	95.78%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.53%	95.64%
CHEMBL2424504	P29375	Lysine-specific demethylase 5A	80.49%	99.23%
CHEMBL3979	Q03181	Peroxisome proliferator-activated receptor delta	80.45%	93.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.43%	99.15%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	80.30%	97.31%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 643975
• LOTUS: LTS0159199
• wikiData: Q28746