Rhapontigenin

Details

• Internal ID: 7865cd1b-8917-423a-b24b-fef74c0401cd
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol
• SMILES (Canonical): COC1=C(C=C(C=C1)C=CC2=CC(=CC(=C2)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)/C=C/C2=CC(=CC(=C2)O)O)O
• InChI: InChI=1S/C15H14O4/c1-19-15-5-4-10(8-14(15)18)2-3-11-6-12(16)9-13(17)7-11/h2-9,16-18H,1H3/b3-2+
• InChI Key: PHMHDRYYFAYWEG-NSCUHMNNSA-N
• Popularity: 63 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.27 g/mol
• Exact Mass: 258.08920892 g/mol
• Topological Polar Surface Area (TPSA): 69.90 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.98
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• 500-65-2
• Protigenin
• Pontigenin
• Rhapontin genin
• 22BG4NNH6W
• 5-[(1E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol
• ?rhapontigenin
• 5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]benzene-1,3-diol
• 5-[(1E)-2-(3-Hydroxy-4-methoxyphenyl)ethenyl]-1,3-benzenediol
• 5-((1E)-2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL)-1,3-BENZENEDIOL
• PRONTIGENIN
• RHAPONTIN AGLYCONE
• UNII-22BG4NNH6W
• CHEMBL113029
• SCHEMBL1486816
• 5-((E)-2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL)BENZENE-1,3-DIOL
• CHEBI:174376
• PHMHDRYYFAYWEG-NSCUHMNNSA-N
• DTXSID501023634
• HMS3648K18
• 4-Methoxystilbene-3,3',5'-triol
• AMY40675
• BCP15039
• HY-N2229
• MFCD00017718
• s9163
• trans-1-(3,5-Dihydroxyphenyl)-2-(3-hydroxy-4-methoxyphenyl)ethylene
• AKOS015915122
• AC-7022
• CCG-267039
• AS-68092
• CS-0019552
• R0089
• 3,3',5-Trihydroxy-4'-methoxy-trans-stilbene
• A827955
• SR-01000946385
• 3,3,5-STILBENETRIOL, 4-METHOXY-, (E)-
• Q7320232
• SR-01000946385-1
• 5-[2-(3-hydroxy-4-methoxy-phenyl)vinyl]benzene-1,3-diol
• Rhapontigenin is known as a natural analog of resveratrol.
• (E)-5-[2-(3-Hydroxy-4-methoxyphenyl)ethenyl]-1,3-benzenediol
• 1,3-BENZENEDIOL, 5-((1E)-2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL)-
• 1,3-BENZENEDIOL, 5-(2-(3-HYDROXY-4-METHOXYPHENYL)ETHENYL)-, (E)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9682	96.82%
Caco-2	+	0.9350	93.50%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5713	57.13%
OATP2B1 inhibitior	-	0.8546	85.46%
OATP1B1 inhibitior	+	0.9560	95.60%
OATP1B3 inhibitior	+	0.9785	97.85%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9338	93.38%
BSEP inhibitior	-	0.5544	55.44%
P-glycoprotein inhibitior	-	0.9219	92.19%
P-glycoprotein substrate	-	0.9599	95.99%
CYP3A4 substrate	-	0.6412	64.12%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	-	0.6581	65.81%
CYP3A4 inhibition	+	0.5185	51.85%
CYP2C9 inhibition	+	0.8148	81.48%
CYP2C19 inhibition	+	0.6868	68.68%
CYP2D6 inhibition	-	0.8877	88.77%
CYP1A2 inhibition	+	0.9192	91.92%
CYP2C8 inhibition	+	0.6032	60.32%
CYP inhibitory promiscuity	+	0.8813	88.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7994	79.94%
Carcinogenicity (trinary)	Non-required	0.5977	59.77%
Eye corrosion	-	0.9623	96.23%
Eye irritation	+	0.9714	97.14%
Skin irritation	-	0.5964	59.64%
Skin corrosion	-	0.6008	60.08%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5662	56.62%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	-	0.6411	64.11%
skin sensitisation	+	0.5135	51.35%
Respiratory toxicity	-	0.8333	83.33%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.7375	73.75%
Nephrotoxicity	-	0.5629	56.29%
Acute Oral Toxicity (c)	III	0.6130	61.30%
Estrogen receptor binding	+	0.9069	90.69%
Androgen receptor binding	+	0.5998	59.98%
Thyroid receptor binding	+	0.6988	69.88%
Glucocorticoid receptor binding	+	0.6034	60.34%
Aromatase binding	+	0.9047	90.47%
PPAR gamma	+	0.8164	81.64%
Honey bee toxicity	-	0.9253	92.53%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9662	96.62%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3194	P02766	Transthyretin	96.28%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	94.68%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.05%	91.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	93.99%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.60%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.31%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.55%	96.09%
CHEMBL1929	P47989	Xanthine dehydrogenase	85.43%	96.12%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.45%	89.62%
CHEMBL4208	P20618	Proteasome component C5	82.90%	90.00%
CHEMBL1255126	O15151	Protein Mdm4	82.80%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.34%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.58%	89.00%
CHEMBL2535	P11166	Glucose transporter	80.92%	98.75%

Plants that contains it

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

Cross-Links

• PubChem: 5320954
• NPASS: NPC247364
• ChEMBL: CHEMBL113029
• LOTUS: LTS0127842
• wikiData: Q7320232