(2S,3S,4R,5R,6S)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)chromenylium-3-yl]oxy-6-methyloxane-3,4,5-triol

Details

• Internal ID: 7f5fae67-915b-4416-928b-b2e1f6826f28
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Anthocyanins > Anthocyanidin-3-O-glycosides
• IUPAC Name: (2S,3S,4R,5R,6S)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)chromenylium-3-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=CC3=C(C=C(C=C3[O+]=C2C4=CC=C(C=C4)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@@H]([C@@H](O1)OC2=CC3=C(C=C(C=C3[O+]=C2C4=CC=C(C=C4)O)O)O)O)O)O
• InChI: InChI=1S/C21H20O9/c1-9-17(25)18(26)19(27)21(28-9)30-16-8-13-14(24)6-12(23)7-15(13)29-20(16)10-2-4-11(22)5-3-10/h2-9,17-19,21,25-27H,1H3,(H2-,22,23,24)/p+1/t9-,17-,18+,19-,21-/m0/s1
• InChI Key: RFOBAKWGJRIIMU-TUJYBLGZSA-O
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₁O₉+
• Molecular Weight: 417.40 g/mol
• Exact Mass: 417.11855724 g/mol
• Topological Polar Surface Area (TPSA): 141.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 1.70
• H-Bond Acceptor: 8
• H-Bond Donor: 6
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4718	47.18%
Caco-2	-	0.7502	75.02%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.5368	53.68%
OATP2B1 inhibitior	+	0.5802	58.02%
OATP1B1 inhibitior	+	0.9121	91.21%
OATP1B3 inhibitior	+	0.9300	93.00%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.6391	63.91%
P-glycoprotein inhibitior	-	0.5272	52.72%
P-glycoprotein substrate	-	0.7639	76.39%
CYP3A4 substrate	+	0.5781	57.81%
CYP2C9 substrate	-	0.8038	80.38%
CYP2D6 substrate	-	0.8214	82.14%
CYP3A4 inhibition	-	0.8493	84.93%
CYP2C9 inhibition	-	0.8089	80.89%
CYP2C19 inhibition	-	0.7440	74.40%
CYP2D6 inhibition	-	0.9213	92.13%
CYP1A2 inhibition	-	0.5798	57.98%
CYP2C8 inhibition	+	0.8444	84.44%
CYP inhibitory promiscuity	-	0.5651	56.51%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5620	56.20%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.7829	78.29%
Skin irritation	-	0.6628	66.28%
Skin corrosion	-	0.9118	91.18%
Ames mutagenesis	-	0.5837	58.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6454	64.54%
Micronuclear	+	0.8400	84.00%
Hepatotoxicity	-	0.7324	73.24%
skin sensitisation	-	0.8804	88.04%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.7989	79.89%
Acute Oral Toxicity (c)	III	0.5235	52.35%
Estrogen receptor binding	+	0.7073	70.73%
Androgen receptor binding	+	0.6935	69.35%
Thyroid receptor binding	+	0.7397	73.97%
Glucocorticoid receptor binding	+	0.8072	80.72%
Aromatase binding	+	0.6672	66.72%
PPAR gamma	+	0.7779	77.79%
Honey bee toxicity	-	0.8305	83.05%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5051	50.51%
Fish aquatic toxicity	+	0.9252	92.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.80%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.39%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.50%	89.00%
CHEMBL2581	P07339	Cathepsin D	93.59%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.18%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.76%	94.00%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	92.02%	95.78%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.52%	96.09%
CHEMBL242	Q92731	Estrogen receptor beta	91.24%	98.35%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.20%	92.94%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.33%	99.15%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.20%	97.36%
CHEMBL1163125	O60885	Bromodomain-containing protein 4	84.35%	97.31%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.13%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.85%	95.56%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	83.82%	91.71%
CHEMBL3194	P02766	Transthyretin	83.22%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.25%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	81.07%	94.73%
CHEMBL4355	O14976	Serine/threonine-protein kinase GAK	80.39%	89.32%
CHEMBL1937	Q92769	Histone deacetylase 2	80.13%	94.75%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.11%	93.10%

Plants that contains it

• Anthemis aciphylla
• Chamaecyparis formosensis
• Chamaecyparis obtusa
• Eucalyptus globulus
• Millettia zechiana
• Persicaria minor

Cross-Links

• PubChem: 154497169
• LOTUS: LTS0203233
• wikiData: Q105143152