(2S)-2-[2-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one

Details

• Internal ID: 16958bbf-ab04-4084-a022-65c62a7e80ee
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > Flavanones
• IUPAC Name: (2S)-2-[2-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxyphenyl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C(C=C(C=C2)O)C3CC(=O)C4=C(C=C(C=C4O3)O)O)O)OC5C(C(C(C(O5)CO)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(C=C(C=C2)O)[C@@H]3CC(=O)C4=C(C=C(C=C4O3)O)O)O)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)O
• InChI: InChI=1S/C27H32O15/c1-9-20(33)25(42-26-23(36)22(35)21(34)18(8-28)41-26)24(37)27(38-9)40-15-3-2-10(29)4-12(15)16-7-14(32)19-13(31)5-11(30)6-17(19)39-16/h2-6,9,16,18,20-31,33-37H,7-8H2,1H3/t9-,16-,18+,20-,21+,22-,23+,24+,25+,26-,27-/m0/s1
• InChI Key: JTQOVBLCPLYXBN-VDBSBOKISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₁₅
• Molecular Weight: 596.50 g/mol
• Exact Mass: 596.17412031 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): -1.46
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.9049	90.49%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.8484	84.84%
OATP1B1 inhibitior	+	0.9065	90.65%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6699	66.99%
P-glycoprotein inhibitior	-	0.7227	72.27%
P-glycoprotein substrate	-	0.5409	54.09%
CYP3A4 substrate	+	0.6499	64.99%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8479	84.79%
CYP3A4 inhibition	-	0.9358	93.58%
CYP2C9 inhibition	-	0.9271	92.71%
CYP2C19 inhibition	-	0.9330	93.30%
CYP2D6 inhibition	-	0.9643	96.43%
CYP1A2 inhibition	-	0.8830	88.30%
CYP2C8 inhibition	+	0.5805	58.05%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9272	92.72%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6480	64.80%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.6000	60.00%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7548	75.48%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.8014	80.14%
Androgen receptor binding	-	0.5641	56.41%
Thyroid receptor binding	+	0.5329	53.29%
Glucocorticoid receptor binding	-	0.4831	48.31%
Aromatase binding	-	0.5129	51.29%
PPAR gamma	+	0.7024	70.24%
Honey bee toxicity	-	0.6984	69.84%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5850	58.50%
Fish aquatic toxicity	+	0.8289	82.89%

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	99.09%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.36%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.82%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.18%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.78%	89.00%
CHEMBL4208	P20618	Proteasome component C5	90.62%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.43%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.16%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.42%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.57%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.70%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.47%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	84.64%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.90%	90.71%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.44%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.22%	86.92%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.47%	99.15%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.12%	96.21%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.64%	95.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.56%	99.23%

Plants that contains it

• Thelypteris acuminata

Cross-Links

• PubChem: 11995074
• LOTUS: LTS0048855
• wikiData: Q105134940