Pinocembrin 7-rhamnosylglucoside

Details

• Internal ID: 081043b5-293e-43da-a4c7-862bc67f5653
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=CC=C5)O)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC=CC=C5)O)CO)O)O)O)O)O
• InChI: InChI=1S/C27H32O13/c1-11-20(31)22(33)24(35)26(36-11)40-25-23(34)21(32)18(10-28)39-27(25)37-13-7-14(29)19-15(30)9-16(38-17(19)8-13)12-5-3-2-4-6-12/h2-8,11,16,18,20-29,31-35H,9-10H2,1H3/t11-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
• InChI Key: UVPBNPUZWAOBQX-AFUJZTQMSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₂O₁₃
• Molecular Weight: 564.50 g/mol
• Exact Mass: 564.18429107 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.87
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

• 13241-31-1
• C09828
• (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-phenyl-2,3-dihydrochromen-4-one
• AC1L9CUZ
• Pinocembrin 7-O-neohesperidoside
• CHEBI:8222
• DTXSID90331830
• Q27107989
• (2S)-5-hydroxy-4-oxo-2-phenyl-3,4-dihydro-2H-1-benzopyran-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
• (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-phenyl-chroman-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.8903	89.03%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.9571	95.71%
Subcellular localzation	Mitochondria	0.6881	68.81%
OATP2B1 inhibitior	-	0.8506	85.06%
OATP1B1 inhibitior	+	0.9370	93.70%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6782	67.82%
P-glycoprotein inhibitior	-	0.8432	84.32%
P-glycoprotein substrate	-	0.7147	71.47%
CYP3A4 substrate	+	0.6374	63.74%
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	+	0.5691	56.91%
CYP inhibitory promiscuity	-	0.7188	71.88%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7023	70.23%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9415	94.15%
Skin irritation	-	0.8192	81.92%
Skin corrosion	-	0.9626	96.26%
Ames mutagenesis	-	0.5670	56.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7064	70.64%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.9312	93.12%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.6977	69.77%
Acute Oral Toxicity (c)	III	0.5734	57.34%
Estrogen receptor binding	+	0.7432	74.32%
Androgen receptor binding	-	0.6192	61.92%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5503	55.03%
Aromatase binding	+	0.5411	54.11%
PPAR gamma	+	0.7193	71.93%
Honey bee toxicity	-	0.7121	71.21%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
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	99.66%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.37%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.50%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.55%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.98%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.77%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.56%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	89.52%	94.73%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.95%	97.36%
CHEMBL4208	P20618	Proteasome component C5	87.78%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.47%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.08%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.49%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.17%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.47%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.56%	96.21%

Plants that contains it

• Glycyrrhiza yunnanensis
• Litchi chinensis
• Nierembergia linariifolia
• Onychium japonicum
• Sparattosperma leucanthum

Cross-Links

• PubChem: 442454
• NPASS: NPC14838
• LOTUS: LTS0148735
• wikiData: Q27107989