Rhaponticin

Details

• Internal ID: ff22fc0f-e2f9-47ce-a3bb-3ac5f3499b8b
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes > Stilbene glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• InChI: InChI=1S/C21H24O9/c1-28-16-5-4-11(8-15(16)24)2-3-12-6-13(23)9-14(7-12)29-21-20(27)19(26)18(25)17(10-22)30-21/h2-9,17-27H,10H2,1H3/b3-2+/t17-,18-,19+,20-,21-/m1/s1
• InChI Key: GKAJCVFOJGXVIA-DXKBKAGUSA-N
• Popularity: 118 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₄O₉
• Molecular Weight: 420.40 g/mol
• Exact Mass: 420.14203234 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.46
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• Rhaponticin
• 155-58-8
• Ponticin
• Rhaponticine
• DTXSID201018153
• K691M2Z08V
• CHEBI:92176
• NSC-43321
• 3-Hydroxy-5-(2-(3-hydroxy-4-methoxyphenyl)ethenyl)phenyl-beta-D-glucopyranoside
• (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• (2S,3R,4S,5S,6R)-2-(3-hydroxy-5-((E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl)phenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• (2S,3R,4S,5S,6R)-2-{3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• RefChem:930705
• 3,5,3'-trihydroxy-4'-methoxystilbene 3-O-beta-D-glucoside
• DTXCID401476400
• 205-845-0
• Rhaponiticin
• MFCD00010117
• CHEBI:8824
• NSC 43321
• (2S,3R,4S,5S,6R)-2-(3-hydroxy-5-((E)-3-hydroxy-4-methoxystyryl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxy-phenyl)vinyl]phenoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol
• beta-D-Glucopyranoside, 3-hydroxy-5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenyl
• UNII-K691M2Z08V
• trans-rhaponticin
• (E)-rhaponticin
• Rose oxide (cis)
• EINECS 205-845-0
• Rhapontin, 95%
• Rhapontin (Standard)
• Rhapontigenin, 3-beta-D-glucopyranoside
• RHAPONTIN [MI]
• Glucopyranoside, rhapontigenin-3, beta-D-
• Spectrum5_001757
• BSPBio_002946
• MLS002207294
• Rhapontin, analytical standard
• SCHEMBL160068
• CHEMBL109266
• orb1301341
• HMS503I09
• HY-N0671R
• BDBM644049
• GLXC-13093
• HY-N0671
• US11866416, Example 12
• CCG-38881
• LMPK13090002
• s9083
• AKOS016034205
• ET07010
• beta-D-Glucopyranoside, 3-hydroxy-5-(2-(3-hydroxy-4-methoxyphenyl)ethenyl)phenyl
• IDI1_001004
• NCGC00178379-01
• 3,3 inverted exclamation marka,5-Trihydroxy-4 inverted exclamation marka-methoxystilbene 3-O-|A-D-glucoside
• AC-34809
• AS-77402
• SMR001306806
• CS-0009703
• R0252
• 155R588
• SR-05000002217
• Q7320229
• SR-05000002217-2
• BRD-K10098805-001-02-0
• Rhapontin;4'-Methoxy-3,3',5-stilbenetriol-3-glucoside
• 3,3',5-Trihydroxy-4'-methoxystilbene 3-O-?-D-glucoside
• 3,3',5-Trihydroxy-4'-methoxystilbene 3-O-beta-D-glucoside
• .beta.-D-Glucopyranoside, 3-hydroxy-5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenyl
• |A-D-Glucopyranoside, 3-hydroxy-5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenyl
• 3-Hydroxy-5-(2-(3-hydroxy-4-methoxyphenyl)vinyl)phenyl-beta-D-glucopyranoside
• 3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenyl beta-D-glucopyranoside
• ss-D-Glucopyranoside, 3-hydroxy-5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenyl
• (2S,3R,4S,5S,6R)-2-{3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy}-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• 3-HYDROXY-5-((1E)-2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL)PHENYL .BETA.-D-GLUCOPYRANOSIDE

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7134	71.34%
Caco-2	-	0.8466	84.66%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.5554	55.54%
OATP2B1 inhibitior	-	0.5676	56.76%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9764	97.64%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5926	59.26%
P-glycoprotein inhibitior	-	0.7669	76.69%
P-glycoprotein substrate	-	0.8639	86.39%
CYP3A4 substrate	+	0.5388	53.88%
CYP2C9 substrate	-	0.6100	61.00%
CYP2D6 substrate	-	0.8073	80.73%
CYP3A4 inhibition	-	0.8070	80.70%
CYP2C9 inhibition	-	0.8461	84.61%
CYP2C19 inhibition	-	0.7952	79.52%
CYP2D6 inhibition	-	0.8974	89.74%
CYP1A2 inhibition	-	0.8653	86.53%
CYP2C8 inhibition	+	0.6272	62.72%
CYP inhibitory promiscuity	-	0.5322	53.22%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6862	68.62%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.8860	88.60%
Skin irritation	-	0.8375	83.75%
Skin corrosion	-	0.9473	94.73%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7336	73.36%
Micronuclear	+	0.5759	57.59%
Hepatotoxicity	-	0.8675	86.75%
skin sensitisation	-	0.8384	83.84%
Respiratory toxicity	-	0.7778	77.78%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.7176	71.76%
Acute Oral Toxicity (c)	III	0.7605	76.05%
Estrogen receptor binding	+	0.5970	59.70%
Androgen receptor binding	-	0.5999	59.99%
Thyroid receptor binding	+	0.6611	66.11%
Glucocorticoid receptor binding	-	0.5474	54.74%
Aromatase binding	+	0.5988	59.88%
PPAR gamma	+	0.6841	68.41%
Honey bee toxicity	-	0.7845	78.45%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.7719	77.19%

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	98.71%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.68%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.27%	96.09%
CHEMBL3194	P02766	Transthyretin	93.73%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.17%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.85%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.10%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	89.92%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.04%	99.17%
CHEMBL2581	P07339	Cathepsin D	87.86%	98.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.64%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.96%	95.89%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.73%	89.62%
CHEMBL1951	P21397	Monoamine oxidase A	84.21%	91.49%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.37%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.93%	95.89%
CHEMBL4208	P20618	Proteasome component C5	80.55%	90.00%

Plants that contains it

• Albizia myriophylla
• Amphorogyne spicata
• Anaphalis lactea
• Anchusa azurea
• Balanophora laxiflora
• Benincasa hispida
• Carduus tenuiflorus
• Chaiturus marrubiastrum
• Commelina communis
• Cryptochilus strictus
• Degenia velebitica
• Delphinium nuttallianum
• Delphinium virgatum
• Dillenia indica
• Dipsacus dipsacoides
• Erythrophleum ivorense
• Eucalyptus rubida
• Grangea maderaspatana
• Guibourtia tessmannii
• Helichrysum chionosphaerum
• Jacquemontia paniculata
• Leptocereus quadricostatus
• Lespedeza tomentosa
• Lupinus argenteus subsp. argenteus
• Mandragora officinarum
• Metrodorea nigra
• Nepeta granatensis
• Onobrychis arenaria
• Petunia inflata
• Phedimus selskanianus
• Photinia serratifolia
• Quercus rubra
• Reynoutria multiflora
• Rheum officinale
• Rheum palmatum
• Rheum rhabarbarum
• Rheum ribes
• Rheum tanguticum
• Rosa villosa
• Salvia greggii
• Senecio behnii
• Senecio praecox
• Sticherus quadripartitus
• Tagetes filifolia
• Tanacetum coccineum
• Verbascum densiflorum

Cross-Links

• PubChem: 637213
• NPASS: NPC98777
• ChEMBL: CHEMBL109266
• LOTUS: LTS0071349
• wikiData: Q7320229