Iridin

Details

• Internal ID: ce196a69-1a61-45e8-a02a-839c3da7e3ea
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavonoid O-glycosides
• IUPAC Name: 5-hydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): COC1=CC(=CC(=C1OC)O)C2=COC3=CC(=C(C(=C3C2=O)O)OC)OC4C(C(C(C(O4)CO)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1OC)O)C2=COC3=CC(=C(C(=C3C2=O)O)OC)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
• InChI: InChI=1S/C24H26O13/c1-32-13-5-9(4-11(26)22(13)33-2)10-8-35-12-6-14(23(34-3)19(29)16(12)17(10)27)36-24-21(31)20(30)18(28)15(7-25)37-24/h4-6,8,15,18,20-21,24-26,28-31H,7H2,1-3H3/t15-,18-,20+,21-,24-/m1/s1
• InChI Key: LNQCUTNLHUQZLR-OZJWLQQPSA-N
• Popularity: 27 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₂₆O₁₃
• Molecular Weight: 522.50 g/mol
• Exact Mass: 522.13734088 g/mol
• Topological Polar Surface Area (TPSA): 194.00 Ų
• XlogP: 0.80
• Atomic LogP (AlogP): 0.08
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 7

Synonyms

• 491-74-7
• UNII-6NTS007OHQ
• 6NTS007OHQ
• CHEBI:5963
• Spectrum_000619
• SpecPlus_000143
• Spectrum2_000198
• Spectrum3_000192
• DTXSID80197689
• irigenin 7-O-beta-D-glucopyranoside
• 5-hydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• Irigenin 7-O-glucoside
• Lridin
• 4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-5-hydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-
• 5-hydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4-oxo-4H-1-benzopyran-7-yl beta-D-glucopyranoside
• 5-HYDROXY-3-(3-HYDROXY-4,5-DIMETHOXYPHENYL)-6-METHOXY-7-((2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL)OXYCHROMEN-4-ONE
• Irisin
• C24H26O13
• Spectrum4_001510
• Spectrum5_000279
• BSPBio_001743
• KBioGR_002179
• KBioSS_001099
• SPECTRUM200793
• DivK1c_006239
• SCHEMBL243567
• SPBio_000155
• CHEMBL487014
• KBio1_001183
• KBio2_001099
• KBio2_003667
• KBio2_006235
• KBio3_001243
• DTXCID90120180
• HY-N3011
• CCG-38404
• MFCD28166495
• SDCCGMLS-0066463.P001
• NCGC00179041-01
• AC-34954
• MS-29677
• CS-0022925
• Q419014
• SR-05000002736
• SR-05000002736-1
• BRD-K22550622-001-02-7
• BRD-K22550622-001-03-5
• 5-hydroxy-3-(3-hydroxy-4,5-dimethoxy-phenyl)-6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one
• 5-hydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
• 5-hydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5088	50.88%
Caco-2	-	0.8491	84.91%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6030	60.30%
OATP2B1 inhibitior	-	0.8410	84.10%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.6264	62.64%
P-glycoprotein inhibitior	-	0.4876	48.76%
P-glycoprotein substrate	-	0.6794	67.94%
CYP3A4 substrate	+	0.6392	63.92%
CYP2C9 substrate	-	0.8485	84.85%
CYP2D6 substrate	-	0.8501	85.01%
CYP3A4 inhibition	-	0.9371	93.71%
CYP2C9 inhibition	-	0.9410	94.10%
CYP2C19 inhibition	-	0.9438	94.38%
CYP2D6 inhibition	-	0.9518	95.18%
CYP1A2 inhibition	-	0.9134	91.34%
CYP2C8 inhibition	+	0.6637	66.37%
CYP inhibitory promiscuity	-	0.7474	74.74%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7050	70.50%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9092	90.92%
Skin irritation	-	0.8406	84.06%
Skin corrosion	-	0.9638	96.38%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4277	42.77%
Micronuclear	+	0.6433	64.33%
Hepatotoxicity	-	0.5625	56.25%
skin sensitisation	-	0.9409	94.09%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7674	76.74%
Acute Oral Toxicity (c)	III	0.6685	66.85%
Estrogen receptor binding	+	0.8329	83.29%
Androgen receptor binding	-	0.5136	51.36%
Thyroid receptor binding	+	0.5579	55.79%
Glucocorticoid receptor binding	+	0.7188	71.88%
Aromatase binding	+	0.5962	59.62%
PPAR gamma	+	0.6929	69.29%
Honey bee toxicity	-	0.7609	76.09%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6049	60.49%
Fish aquatic toxicity	+	0.7605	76.05%

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	99.07%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	95.84%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.54%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.84%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.90%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.66%	85.14%
CHEMBL4302	P08183	P-glycoprotein 1	93.54%	92.98%
CHEMBL3060	Q9Y345	Glycine transporter 2	92.32%	99.17%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.59%	96.21%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.09%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.49%	86.92%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	86.33%	95.64%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.17%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.87%	96.00%

Plants that contains it

• Erythrina sigmoidea
• Iris domestica
• Iris hookeriana
• Iris kemaonensis
• Iris milesii
• Iris pallida
• Iris pallida subsp. cengialti
• Iris pseudacorus
• Iris pseudopumila
• Iris tectorum
• Juniperus polycarpos var. seravschanica
• Lantana camara
• Scutellaria baicalensis

Cross-Links

• PubChem: 5281777
• NPASS: NPC224462
• LOTUS: LTS0254558
• wikiData: Q419014