Robinin

Details

• Internal ID: 3ac3827f-279e-47b1-882d-c9d297b55d19
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• InChI: InChI=1S/C33H40O19/c1-10-19(36)23(40)26(43)31(47-10)46-9-17-21(38)25(42)28(45)33(51-17)52-30-22(39)18-15(35)7-14(49-32-27(44)24(41)20(37)11(2)48-32)8-16(18)50-29(30)12-3-5-13(34)6-4-12/h3-8,10-11,17,19-21,23-28,31-38,40-45H,9H2,1-2H3/t10-,11-,17+,19-,20-,21-,23+,24+,25-,26+,27+,28+,31+,32-,33-/m0/s1
• InChI Key: PEFASEPMJYRQBW-HKWQTAEVSA-N
• Popularity: 45 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₉
• Molecular Weight: 740.70 g/mol
• Exact Mass: 740.21637904 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.89
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 8

Synonyms

• 301-19-9
• 75RT1VGM60
• DTXSID401031393
• CHEBI:8878
• 4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-galactopyranosyl)oxy)-7-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-
• 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
• 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
• NSC-9222
• 5-hydroxy-2-(4-hydroxyphenyl)-7-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-3-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxymethyl)tetrahydropyran-2-yl)oxy-chromen-4-one
• 5-hydroxy-2-(4-hydroxyphenyl)-7-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-3-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl)oxan-2-yl)oxychromen-4-one
• RefChem:179724
• DTXCID101784927
• 206-113-3
• 5-hydroxy-2-(4-hydroxyphenyl)-7-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl)oxan-2-yl)oxychromen-4-one
• Kaempferol-3-O-gal-rham-7-O-rham
• EINECS 206-113-3
• NSC 9222
• Kaempferol-3-O-robinoside-7-O-rhamnoside
• 3-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-galactopyranosyl)oxy)-7-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• UNII-75RT1VGM60
• Robinin (Standard)
• AC1NQYWP
• SpecPlus_000819
• ROBININ [MI]
• DivK1c_006915
• SCHEMBL241939
• MEGxp0_001943
• orb1304708
• SCHEMBL29849153
• HY-N1346R
• KBio1_001859
• GLXC-14189
• Robinin, >=90.0% (HPLC)
• HY-N1346
• ZINC85643559
• AKOS032948817
• OR34983
• AC-36973
• DA-57495
• Kaempferol 3-O-robinoside-7-O-rhamnoside
• kaempherol-3-O-robinoside-7-O-rhamnoside
• MS-31289
• CS-0016754
• NS00015843
• Q7352943
• Kaempferol 3-O-beta-robinoside 7-O-alpha-L-rhamnopyranoside
• Kaempferol-3-O-robinoside-7-O-rhamnoside;Kaempferol-3-O-gal-rham-7-O-rham
• 4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-galactopyranosyl)oxy)-7-((6-deoxy-.alpha.-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl
• 4H-1-BENZOPYRAN-4-ONE, 3-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GALACTOPYRANOSYL)OXY)-7-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-5-HYDROXY-2-(4-HYDROXYPHENYL)-
• 5-Hydroxy-2-(4-hydroxyphenyl)-3-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-7-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
• 7-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-galactopyranoside
• KAEMPFEROL 3-O-.ALPHA.-L-RHAMNOPYRANOSYL-(1->6)-.BETA.-D-GALACTOPYRANOSYL 7-O-.ALPHA.-L-RHAMNOPYRANOSIDE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4659	46.59%
Caco-2	-	0.9089	90.89%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7552	75.52%
OATP2B1 inhibitior	-	0.5703	57.03%
OATP1B1 inhibitior	+	0.9118	91.18%
OATP1B3 inhibitior	+	0.9107	91.07%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9055	90.55%
P-glycoprotein inhibitior	-	0.4789	47.89%
P-glycoprotein substrate	+	0.5348	53.48%
CYP3A4 substrate	+	0.6197	61.97%
CYP2C9 substrate	-	0.7354	73.54%
CYP2D6 substrate	-	0.8607	86.07%
CYP3A4 inhibition	-	0.8904	89.04%
CYP2C9 inhibition	-	0.9134	91.34%
CYP2C19 inhibition	-	0.9158	91.58%
CYP2D6 inhibition	-	0.9500	95.00%
CYP1A2 inhibition	-	0.8713	87.13%
CYP2C8 inhibition	+	0.7912	79.12%
CYP inhibitory promiscuity	-	0.6602	66.02%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7067	70.67%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9034	90.34%
Skin irritation	-	0.8277	82.77%
Skin corrosion	-	0.9610	96.10%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7641	76.41%
Micronuclear	+	0.7292	72.92%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.9381	93.81%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.8817	88.17%
Acute Oral Toxicity (c)	III	0.6245	62.45%
Estrogen receptor binding	+	0.7770	77.70%
Androgen receptor binding	+	0.6139	61.39%
Thyroid receptor binding	-	0.4931	49.31%
Glucocorticoid receptor binding	+	0.5430	54.30%
Aromatase binding	+	0.5329	53.29%
PPAR gamma	+	0.7201	72.01%
Honey bee toxicity	-	0.7809	78.09%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5450	54.50%
Fish aquatic toxicity	+	0.9179	91.79%

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	99.27%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.29%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.69%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.86%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.16%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.39%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	94.15%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	93.89%	95.64%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.13%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.44%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.15%	85.14%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.36%	95.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.32%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.76%	97.09%
CHEMBL242	Q92731	Estrogen receptor beta	84.57%	98.35%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.42%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.21%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.25%	97.36%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.17%	86.92%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.94%	94.80%
CHEMBL4208	P20618	Proteasome component C5	80.41%	90.00%
CHEMBL3194	P02766	Transthyretin	80.08%	90.71%

Plants that contains it

• Abies alba
• Abies marocana
• Aconitum anthora
• Ampelocera edentula
• Angelica acutiloba
• Arnica mollis
• Aspilia foliosa
• Astragalus dipelta
• Astragalus eupeplus
• Astragalus falcatus
• Astragalus laxmannii
• Astragalus laxmannii subsp. laxmannii
• Astragalus levieri
• Astragalus wagneri
• Barringtonia acutangula
• Brassica carinata
• Bryonia alba
• Canavalia gladiata
• Carpha glomerata
• Cephalocereus senilis
• Corydalis densiflora
• Craibiodendron yunnanense
• Crotalaria trichotoma
• Croton gratissimus
• Cyanostegia angustifolia
• Cyperus pedunculatus
• Dactylorhiza viridis
• Dalbergia congestiflora
• Desmodium canadense
• Diplopterygium glaucum
• Embelia ribes
• Eucalyptus resinifera
• Euphrasia nana
• Eurycoma harmandiana
• Ginkgo biloba
• Gliricidia sepium
• Glycine max
• Ixeris japonica
• Khaya grandifoliola
• Lysimachia fordiana
• Mabea fistulifera
• Melilotus albus
• Melilotus officinalis
• Melilotus officinalis
• Napoleonaea vogelii
• Orthosiphon aristatus
• Oxytropis falcata
• Oxytropis muricata
• Oxytropis muricata subsp. varlakovii
• Pterolobium hexapetalum
• Pueraria montana var. lobata
• Ranunculus asiaticus
• Rhazya stricta
• Schleichera oleosa
• Schultesia guianensis
• Sinapis alba
• Solanum lanceolatum
• Triclisia subcordata
• Trifolium ambiguum
• Viburnum erubescens
• Vigna umbellata
• Vinca erecta
• Vinca major
• Wikstroemia indica
• Xanthorhiza simplicissima

Cross-Links

• PubChem: 5281693
• NPASS: NPC226333
• LOTUS: LTS0260167
• wikiData: Q7352943