Isorhapontin

Details

• Internal ID: 4e9a6dad-e9e3-44e4-a376-efc496b3f156
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes > Stilbene glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC2=CC(=CC(=C2)OC3C(C(C(C(O3)CO)O)O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C2=CC(=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O)O)O
• InChI: InChI=1S/C21H24O9/c1-28-16-8-11(4-5-15(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: KLPUXMNQDCUPNO-DXKBKAGUSA-N
• Popularity: 10 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: 1.10
• Atomic LogP (AlogP): 0.46
• H-Bond Acceptor: 9
• H-Bond Donor: 6
• Rotatable Bonds: 6

Synonyms

• 32727-29-0
• CHEBI:6053
• Isorhapontigenin 3-O-beta-D-glucoside
• (2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• E-Isorhapontin
• CHEMBL113339
• MEGxp0_000822
• ACon1_001069
• DTXSID701031823
• LMPK13090010
• AKOS040762908
• Isorhapontin, >=95% (LC/MS-ELSD)
• NCGC00169707-01
• NCGC00169707-02
• ISORHAPONTIGENIN 3-(.BETA.-D-GLUCOPYRANOSIDE)
• Q18352366
• 3,4',5-TRIHYDROXY-3'-METHOXYSTILBENE 3-O-.BETA.-D-GLUCOPYRANOSIDE
• (2S,3R,4S,5S,6R)-2-(3-Hydroxy-5-((E)-4-hydroxy-3-methoxystyryl)phenoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• .BETA.-D-GLUCOPYRANOSIDE, 3-HYDROXY-5-(2-(4-HYDROXY-3-METHOXYPHENYL)ETHENYL)PHENYL, (E)-
• 3-HYDROXY-5-((1E)-2-(4-HYDROXY-3-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	-	0.8857	88.57%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5554	55.54%
OATP2B1 inhibitior	+	0.5713	57.13%
OATP1B1 inhibitior	+	0.9389	93.89%
OATP1B3 inhibitior	+	0.9764	97.64%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.6966	69.66%
P-glycoprotein inhibitior	-	0.7548	75.48%
P-glycoprotein substrate	-	0.8993	89.93%
CYP3A4 substrate	+	0.5353	53.53%
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	+	0.6286	62.86%
CYP inhibitory promiscuity	-	0.5322	53.22%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6862	68.62%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9025	90.25%
Skin irritation	-	0.8375	83.75%
Skin corrosion	-	0.9473	94.73%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6745	67.45%
Micronuclear	+	0.5759	57.59%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8384	83.84%
Respiratory toxicity	-	0.7556	75.56%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.7478	74.78%
Acute Oral Toxicity (c)	III	0.7605	76.05%
Estrogen receptor binding	+	0.6464	64.64%
Androgen receptor binding	-	0.5235	52.35%
Thyroid receptor binding	+	0.6391	63.91%
Glucocorticoid receptor binding	-	0.5765	57.65%
Aromatase binding	+	0.6956	69.56%
PPAR gamma	+	0.7173	71.73%
Honey bee toxicity	-	0.7845	78.45%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
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	99.51%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.66%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.76%	96.09%
CHEMBL3194	P02766	Transthyretin	93.96%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.88%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.21%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	91.47%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.53%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	90.49%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.00%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.26%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.18%	86.92%
CHEMBL2581	P07339	Cathepsin D	82.93%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.64%	99.15%
CHEMBL4208	P20618	Proteasome component C5	81.42%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.37%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	80.66%	95.93%

Plants that contains it

• Achlys triphylla
• Albizia procera
• Artemisia giraldii
• Bulbophyllum protractum
• Calystegia pubescens
• Cypripedium calceolus
• Diospyros japonica
• Gnetum montanum
• Hortonia floribunda
• Lactuca sativa
• Lampranthus sociorum
• Perymenium mendezii
• Picea abies
• Picea glauca
• Picea koraiensis
• Picea sitchensis
• Pinus koraiensis
• Pongamia pinnata
• Protium tonkinense
• Rheum rhabarbarum
• Salacia lehmbachii
• Seriphidium porrectum
• Tarchonanthus camphoratus
• Typha latifolia
• Uncaria rhynchophylla
• Veratrum taliense

Cross-Links

• PubChem: 5281716
• NPASS: NPC212770
• LOTUS: LTS0038705
• wikiData: Q18352366