Didymin

Details

• Internal ID: 97fdee57-ff3f-4cce-a849-31cbf18b5bdd
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: (2S)-5-hydroxy-2-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=C(C=C5)OC)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC=C(C=C5)OC)O)O)O)O)O)O)O
• InChI: InChI=1S/C28H34O14/c1-11-21(31)23(33)25(35)27(39-11)38-10-19-22(32)24(34)26(36)28(42-19)40-14-7-15(29)20-16(30)9-17(41-18(20)8-14)12-3-5-13(37-2)6-4-12/h3-8,11,17,19,21-29,31-36H,9-10H2,1-2H3/t11-,17-,19+,21-,22+,23+,24-,25+,26+,27+,28+/m0/s1
• InChI Key: RMCRQBAILCLJGU-HIBKWJPLSA-N
• Popularity: 24 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₄O₁₄
• Molecular Weight: 594.60 g/mol
• Exact Mass: 594.19485575 g/mol
• Topological Polar Surface Area (TPSA): 214.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.86
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• 14259-47-3
• Neoponcirin
• Isosakuranetin-7-O-rutinoside
• Didymine
• 02Q5OS3TU3
• Isosakuranetin-7-beta-rutinoside
• EINECS 238-139-6
• Isosakuranetin 7-rutinoside
• UNII-02Q5OS3TU3
• CITRIFOLIOL-7-O-RUTINOSIDE
• (2S)-5-hydroxy-2-(4-methoxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• (S)-7-[[6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl]oxy]-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-4H-benzopyran-4-one
• DIDYMIN (USP-RS)
• DIDYMIN [USP-RS]
• Isosakuranetin 7-O-rutinoside
• 4'-METHOXY-5,7-DIHYDROXYFLAVANONE 7-O-RUTINOSIDE
• (S)-7-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-4H-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 7-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-methoxyphenyl)-, (S)-
• Didymin, analytical standard
• Iso-sakuranetin-7-putinoside
• SCHEMBL497764
• DTXSID90931536
• CHEBI:176179
• HY-N2068
• MFCD00151177
• s9235
• AKOS016010158
• CCG-270180
• CS-T-59226
• NCGC00163539-01
• AC-34874
• AS-75739
• CS-0018573
• A885172
• SR-05000002279
• SR-05000002279-2
• Q63399321
• Z3235033284
• FLAVANONE, 5,7-DIHYDROXY-4'-METHOXY-, 7beta-RUTINOSIDE
• FLAVANONE, 5,7-DIHYDROXY-4'-METHOXY-, 7.BETA.-RUTINOSIDE
• (2S)-7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
• (2S)-7-((6-O-(6-DEOXY-alpha-L-MANNOPYRANOSYL)-beta-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONE
• (S)-5-hydroxy-2-(4-methoxyphenyl)-7-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)methyl)tetrahydro-2H-pyran-2-yloxy)chroman-4-one
• 4H-1-BENZOPYRAN-4-ONE, 7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-METHOXYPHENYL)-, (2S)-
• 4H-1-BENZOPYRAN-4-ONE, 7-((6-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-.BETA.-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-METHOXYPHENYL)-, (S)-
• 4H-1-BENZOPYRAN-4-ONE, 7-((6-O-(6-DEOXY-alpha-L-MANNOPYRANOSYL)-beta-D-GLUCOPYRANOSYL)OXY)-2,3-DIHYDRO-5-HYDROXY-2-(4-METHOXYPHENYL)-, (2S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4777	47.77%
Caco-2	-	0.8707	87.07%
Blood Brain Barrier	-	0.9250	92.50%
Human oral bioavailability	-	0.8571	85.71%
Subcellular localzation	Mitochondria	0.6902	69.02%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	+	0.9284	92.84%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7749	77.49%
P-glycoprotein inhibitior	-	0.8489	84.89%
P-glycoprotein substrate	-	0.6365	63.65%
CYP3A4 substrate	+	0.6349	63.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8428	84.28%
CYP3A4 inhibition	-	0.8619	86.19%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.4853	48.53%
CYP inhibitory promiscuity	-	0.6670	66.70%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6995	69.95%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9215	92.15%
Skin irritation	-	0.8249	82.49%
Skin corrosion	-	0.9594	95.94%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7341	73.41%
Micronuclear	+	0.7492	74.92%
Hepatotoxicity	-	0.8333	83.33%
skin sensitisation	-	0.9436	94.36%
Respiratory toxicity	-	0.7000	70.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.6625	66.25%
Nephrotoxicity	-	0.7701	77.01%
Acute Oral Toxicity (c)	III	0.6904	69.04%
Estrogen receptor binding	+	0.8064	80.64%
Androgen receptor binding	-	0.6934	69.34%
Thyroid receptor binding	+	0.5642	56.42%
Glucocorticoid receptor binding	+	0.5967	59.67%
Aromatase binding	-	0.4850	48.50%
PPAR gamma	+	0.7244	72.44%
Honey bee toxicity	-	0.7836	78.36%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.8477	84.77%

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	99.71%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.85%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.16%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.78%	98.95%
CHEMBL4208	P20618	Proteasome component C5	94.36%	90.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.10%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.20%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.71%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.30%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.37%	99.15%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.36%	89.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.25%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.95%	95.89%
CHEMBL3401	O75469	Pregnane X receptor	87.70%	94.73%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.84%	86.92%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	86.57%	94.80%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.11%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.02%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.27%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	80.75%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.13%	94.45%

Plants that contains it

• Citrus × aurantium
• Citrus cavaleriei
• Citrus deliciosa
• Citrus maxima
• Citrus trifoliata
• Clinopodium chinense
• Clinopodium laxiflorum
• Cyclotrichium niveum
• Mentha canadensis

Cross-Links

• PubChem: 16760075
• NPASS: NPC70206
• LOTUS: LTS0187794
• wikiData: Q63399321