Betanine

Details

• Internal ID: 0f0a20fb-7e41-46e2-8282-2bf52a4113d5
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbohydrates and carbohydrate conjugates > Glycosyl compounds > Phenolic glycosides
• IUPAC Name: (2S)-4-[(E)-2-[(2S)-2-carboxy-6-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydroindol-1-yl]ethenyl]-2,3-dihydropyridine-2,6-dicarboxylic acid
• SMILES (Canonical): C1C(N=C(C=C1C=CN2C(CC3=CC(=C(C=C32)O)OC4C(C(C(C(O4)CO)O)O)O)C(=O)O)C(=O)O)C(=O)O
• SMILES (Isomeric): C1[C@H](N=C(C=C1/C=C/N2[C@@H](CC3=CC(=C(C=C32)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)C(=O)O)C(=O)O)C(=O)O
• InChI: InChI=1S/C24H26N2O13/c27-8-17-18(29)19(30)20(31)24(39-17)38-16-6-10-5-14(23(36)37)26(13(10)7-15(16)28)2-1-9-3-11(21(32)33)25-12(4-9)22(34)35/h1-3,6-7,12,14,17-20,24,27-31H,4-5,8H2,(H,32,33)(H,34,35)(H,36,37)/b2-1+/t12-,14-,17+,18+,19-,20+,24+/m0/s1
• InChI Key: CTMLKIKAUFEMLE-FTNGGYTGSA-N
• Popularity: 127 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₆N₂O₁₃
• Molecular Weight: 550.50 g/mol
• Exact Mass: 550.14348889 g/mol
• Topological Polar Surface Area (TPSA): 247.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -1.79
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

• Phytolaccanin
• 5YJC992ZP6
• UNII-5YJC992ZP6
• (2S)-4-[2-[(2S)-2-Carboxy-5-(beta-D-glucopyranosyloxy)-2,3-dihydro-6-hydroxy-1H-indol-1-yl]ethenyl]-2,3-dihydro-2,6-pyridinedicarboxylic acid
• Betanidin 5-beta-D-glucopyranoside
• EINECS 231-628-5
• NSC 170989
• 2,6-PYRIDINEDICARBOXYLIC ACID, 4-(2-(2-CARBOXY-5-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-6-HYDROXY-1H-INDOL-1-YL)ETHENYL)-2,3-DIHYDRO-, (S-(R*,R*))-
• BETANIN [MI]
• INS-162BETANIN
• E-162BETANIN
• (15S)-BETANIN
• INS NO.162BETANIN
• DTXSID80997924
• (S-(R*,R*))-4-(2-(2-Carboxy-5-(beta-D-glucopyranosyloxy)-2,3-dihydro-6-hydroxy-1H-indol-1-yl)vinyl)-2,3-dihydropyridine-2,6-dicarboxylic acid
• (S-(R*,R*-(E,E)))-2-Carboxy-1-((2,6-dicarboxy-2,3-dihydro-4(1H)-pyridinylidene)ethylidene)-5-(beta-D-glucopyranosyloxy)-2,3-dihydro-6-hydroxy-1H-indolium hydroxide, inner salt
• 2,6-Pyridinedicarboxylic acid, 4-(2-(2-carboxy-5-(beta-D-glucopyranosyloxy)-2,3-dihydro-6-hydroxy-1H-indol-1-yl)ethenyl)-2,3-dihydro-, (S-(R*,R*))-
• AKOS040750788
• HY-112578
• BETANIDIN 5-.BETA.-D-GLUCOPYRANOSIDE
• CS-0046867
• Q420138
• (S-(R*,R*))-4-(2-(2-CARBOXY-5-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-6-HYDROXY-1H-INDOL-1-YL)VINYL)-2,3-DIHYDROPYRIDINE-2,6-DICARBOXYLIC ACID
• (S-(R*,R*-(E,E)))-2-CARBOXY-1-((2,6-DICARBOXY-2,3-DIHYDRO-4(1H)-PYRIDINYLIDENE ETHYLIDENE)-5-(.BETA.-D-GLUCOPYRANOSYLOXY)-2,3-DIHYDRO-6-HYDROXY-1H-INDOLIUM HYDROXIDE, INNER SALT

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5855	58.55%
Caco-2	-	0.9024	90.24%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.4917	49.17%
OATP2B1 inhibitior	-	0.8464	84.64%
OATP1B1 inhibitior	+	0.8639	86.39%
OATP1B3 inhibitior	+	0.9366	93.66%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6617	66.17%
P-glycoprotein inhibitior	-	0.4777	47.77%
P-glycoprotein substrate	-	0.6444	64.44%
CYP3A4 substrate	+	0.6383	63.83%
CYP2C9 substrate	-	0.7950	79.50%
CYP2D6 substrate	-	0.8458	84.58%
CYP3A4 inhibition	-	0.8607	86.07%
CYP2C9 inhibition	-	0.7404	74.04%
CYP2C19 inhibition	-	0.7887	78.87%
CYP2D6 inhibition	-	0.8475	84.75%
CYP1A2 inhibition	-	0.5623	56.23%
CYP2C8 inhibition	+	0.5927	59.27%
CYP inhibitory promiscuity	-	0.7180	71.80%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5595	55.95%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.9244	92.44%
Skin irritation	-	0.7765	77.65%
Skin corrosion	-	0.9324	93.24%
Ames mutagenesis	-	0.6623	66.23%
Human Ether-a-go-go-Related Gene inhibition	-	0.4126	41.26%
Micronuclear	+	0.8800	88.00%
Hepatotoxicity	-	0.7196	71.96%
skin sensitisation	-	0.8282	82.82%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.7271	72.71%
Acute Oral Toxicity (c)	III	0.5907	59.07%
Estrogen receptor binding	+	0.6525	65.25%
Androgen receptor binding	+	0.5382	53.82%
Thyroid receptor binding	-	0.5668	56.68%
Glucocorticoid receptor binding	-	0.4842	48.42%
Aromatase binding	+	0.5295	52.95%
PPAR gamma	+	0.6252	62.52%
Honey bee toxicity	-	0.8228	82.28%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.8491	84.91%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.29%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.30%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.53%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.89%	99.17%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.70%	93.40%
CHEMBL2581	P07339	Cathepsin D	88.20%	98.95%
CHEMBL3714130	P46095	G-protein coupled receptor 6	87.61%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.28%	95.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.58%	95.89%
CHEMBL3891	P07384	Calpain 1	86.53%	93.04%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.18%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.63%	99.23%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.96%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.64%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.26%	94.45%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.43%	95.78%

Plants that contains it

• Phytolacca acinosa

Cross-Links

• PubChem: 6540685
• NPASS: NPC202432