(2S)-1-[(2E)-2-[(2S)-6-carboxy-2-carboxylato-2,3-dihydro-1H-pyridin-1-ium-4-ylidene]ethylidene]-5-[(3R,4S,5S,6R)-3-[(3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-oxido-2,3-dihydroindol-1-ium-2-carboxylate

Details

• Internal ID: 0a18cae5-d81c-4b8a-9398-fb938fd2f28d
• Taxonomy: Alkaloids and derivatives > Betalains > Betacyanins and derivatives
• IUPAC Name: (2S)-1-[(2E)-2-[(2S)-6-carboxy-2-carboxylato-2,3-dihydro-1H-pyridin-1-ium-4-ylidene]ethylidene]-5-[(3R,4S,5S,6R)-3-[(3R,4S,5S,6S)-6-carboxylato-3,4,5-trihydroxyoxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-oxido-2,3-dihydroindol-1-ium-2-carboxylate
• SMILES (Canonical): C1C([NH2+]C(=CC1=CC=[N+]2C(CC3=CC(=C(C=C32)[O-])OC4C(C(C(C(O4)CO)O)O)OC5C(C(C(C(O5)C(=O)[O-])O)O)O)C(=O)[O-])C(=O)O)C(=O)[O-]
• SMILES (Isomeric): C\1[C@H]([NH2+]C(=C/C1=C/C=[N+]2[C@@H](CC3=CC(=C(C=C32)[O-])OC4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)OC5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)[O-])O)O)O)C(=O)[O-])C(=O)O)C(=O)[O-]
• InChI: InChI=1S/C30H34N2O19/c33-8-17-18(35)20(37)24(51-29-22(39)19(36)21(38)23(50-29)28(46)47)30(49-17)48-16-6-10-5-14(27(44)45)32(13(10)7-15(16)34)2-1-9-3-11(25(40)41)31-12(4-9)26(42)43/h1-3,6-7,12,14,17-24,29-30,33,35-39H,4-5,8H2,(H5,34,40,41,42,43,44,45,46,47)/p-2/t12-,14-,17+,18+,19-,20-,21-,22+,23-,24+,29?,30?/m0/s1
• InChI Key: ATSKDYKYMQVTGH-FIQIUYQZSA-L
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₂N₂O₁₉-₂
• Molecular Weight: 724.60 g/mol
• Exact Mass: 724.15992680 g/mol
• Topological Polar Surface Area (TPSA): 359.00 Ų
• XlogP: -2.50
• Atomic LogP (AlogP): -10.11
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5728	57.28%
Caco-2	-	0.8992	89.92%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Nucleus	0.4857	48.57%
OATP2B1 inhibitior	-	0.7163	71.63%
OATP1B1 inhibitior	+	0.8509	85.09%
OATP1B3 inhibitior	+	0.9364	93.64%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.5562	55.62%
P-glycoprotein inhibitior	+	0.6134	61.34%
P-glycoprotein substrate	+	0.5919	59.19%
CYP3A4 substrate	+	0.6893	68.93%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8461	84.61%
CYP3A4 inhibition	-	0.8958	89.58%
CYP2C9 inhibition	-	0.7912	79.12%
CYP2C19 inhibition	-	0.8070	80.70%
CYP2D6 inhibition	-	0.8362	83.62%
CYP1A2 inhibition	-	0.6425	64.25%
CYP2C8 inhibition	+	0.7381	73.81%
CYP inhibitory promiscuity	-	0.8814	88.14%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.4905	49.05%
Eye corrosion	-	0.9832	98.32%
Eye irritation	-	0.9155	91.55%
Skin irritation	-	0.7734	77.34%
Skin corrosion	-	0.9267	92.67%
Ames mutagenesis	-	0.5893	58.93%
Human Ether-a-go-go-Related Gene inhibition	-	0.4191	41.91%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.8070	80.70%
skin sensitisation	-	0.8264	82.64%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	-	0.7827	78.27%
Acute Oral Toxicity (c)	III	0.5970	59.70%
Estrogen receptor binding	+	0.7702	77.02%
Androgen receptor binding	+	0.6267	62.67%
Thyroid receptor binding	+	0.5137	51.37%
Glucocorticoid receptor binding	-	0.4700	47.00%
Aromatase binding	+	0.5741	57.41%
PPAR gamma	+	0.7032	70.32%
Honey bee toxicity	-	0.6330	63.30%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.7278	72.78%

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	97.81%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.50%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.33%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.79%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.98%	96.95%
CHEMBL226	P30542	Adenosine A1 receptor	87.98%	95.93%
CHEMBL2581	P07339	Cathepsin D	86.85%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.44%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.27%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.76%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.53%	97.36%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.34%	82.50%

Plants that contains it

• Celosia argentea

Cross-Links

• PubChem: 54740356
• NPASS: NPC158997