(2S)-1-[(2E)-2-[(2S)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene]-6-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-indolin-1-ium-2-carboxylate

Details

• Internal ID: dd4a9ef5-0ddb-480b-8ec8-246bbd63cfae
• Taxonomy: Alkaloids and derivatives > Betalains > Betacyanins and derivatives
• IUPAC Name: (2S)-1-[(2E)-2-[(2S)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene]-6-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydroindol-1-ium-2-carboxylate
• SMILES (Canonical): C1C(NC(=CC1=CC=[N+]2C(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): C\1[C@H](NC(=C/C1=C/C=[N+]2[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/h1-3,6-7,12,14,17-20,24,27,29-31H,4-5,8H2,(H4,28,32,33,34,35,36,37)/t12-,14-,17+,18+,19-,20+,24+/m0/s1
• InChI Key: DHHFDKNIEVKVKS-FMOSSLLZSA-N
• Popularity: 0 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): 249.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -3.70
• H-Bond Acceptor: 12
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

• C08540
• Beta vulgaris
• (2S)-1-[(2E)-2-[(2S)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene]-6-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-indolin-1-ium-2-carboxylate
• CHEBI:3080
• C24H26N2O13
• C24-H26-N2-O13
• AC1O44K9
• SCHEMBL21638973
• DHHFDKNIEVKVKS-FMOSSLLZSA-N
• 2,6-Pyridinedicarboxylic acid, 4-[2-[(2S)-2-carboxy-5-(.beta.-D-glucopyranosyloxy)-2,3-dihydro-6-hydroxy-1H-indol-1-yl]ethenyl]-2,3-dihydro-, (2S)-
• (2S)-1-[(2E)-2-[(2S)-2,6-dicarboxy-2,3-dihydro-1H-pyridin-4-ylidene]ethylidene]-6-hydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydroindol-1-ium-2-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5898	58.98%
Caco-2	-	0.9245	92.45%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Nucleus	0.4320	43.20%
OATP2B1 inhibitior	-	0.8467	84.67%
OATP1B1 inhibitior	+	0.8424	84.24%
OATP1B3 inhibitior	+	0.9349	93.49%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.8008	80.08%
P-glycoprotein inhibitior	-	0.5396	53.96%
P-glycoprotein substrate	+	0.5226	52.26%
CYP3A4 substrate	+	0.6529	65.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8531	85.31%
CYP3A4 inhibition	-	0.8947	89.47%
CYP2C9 inhibition	-	0.7692	76.92%
CYP2C19 inhibition	-	0.8021	80.21%
CYP2D6 inhibition	-	0.8291	82.91%
CYP1A2 inhibition	-	0.6095	60.95%
CYP2C8 inhibition	+	0.6484	64.84%
CYP inhibitory promiscuity	-	0.8348	83.48%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5301	53.01%
Eye corrosion	-	0.9837	98.37%
Eye irritation	-	0.9382	93.82%
Skin irritation	-	0.7742	77.42%
Skin corrosion	-	0.9293	92.93%
Ames mutagenesis	-	0.5223	52.23%
Human Ether-a-go-go-Related Gene inhibition	-	0.3731	37.31%
Micronuclear	+	0.9000	90.00%
Hepatotoxicity	-	0.8728	87.28%
skin sensitisation	-	0.8278	82.78%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9375	93.75%
Nephrotoxicity	-	0.8129	81.29%
Acute Oral Toxicity (c)	III	0.6038	60.38%
Estrogen receptor binding	+	0.6989	69.89%
Androgen receptor binding	+	0.5862	58.62%
Thyroid receptor binding	-	0.5185	51.85%
Glucocorticoid receptor binding	-	0.4636	46.36%
Aromatase binding	+	0.5697	56.97%
PPAR gamma	+	0.6559	65.59%
Honey bee toxicity	-	0.7302	73.02%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6900	69.00%
Fish aquatic toxicity	+	0.8022	80.22%

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	97.38%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.51%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.28%	99.17%
CHEMBL2581	P07339	Cathepsin D	92.88%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.99%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.89%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.45%	90.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.17%	96.95%
CHEMBL3194	P02766	Transthyretin	84.07%	90.71%
CHEMBL220	P22303	Acetylcholinesterase	83.35%	94.45%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	82.68%	89.67%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.17%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.11%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.96%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.99%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.91%	92.94%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.01%	97.21%

Plants that contains it

• Allium nutans
• Amaranthus caudatus
• Amaranthus cruentus
• Beta vulgaris
• Dalea gattingeri
• Lampranthus peersii
• Opuntia ficus-indica
• Phytolacca americana
• Portulaca grandiflora
• Portulaca oleracea
• Selenicereus monacanthus
• Solanum incanum
• Stachys mucronata

Cross-Links

• PubChem: 11953901
• NPASS: NPC90672
• LOTUS: LTS0188491
• wikiData: Q420138