(3S)-3-(1,3-benzodioxol-5-ylmethyl)-5-hydroxy-6-methyl-4-oxo-7-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromene-8-carbaldehyde

Details

• Internal ID: 59ef1582-30ad-48cd-bc8f-c49d8278691e
• Taxonomy: Phenylpropanoids and polyketides > Homoisoflavonoids > Homoisoflavans > Homoisoflavanones
• IUPAC Name: (3S)-3-(1,3-benzodioxol-5-ylmethyl)-5-hydroxy-6-methyl-4-oxo-7-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromene-8-carbaldehyde
• SMILES (Canonical): CC1=C(C2=C(C(=C1OC3C(C(C(C(O3)CO)O)O)O)C=O)OCC(C2=O)CC4=CC5=C(C=C4)OCO5)O
• SMILES (Isomeric): CC1=C(C2=C(C(=C1O[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)O)O)C=O)OC[C@@H](C2=O)CC4=CC5=C(C=C4)OCO5)O
• InChI: InChI=1S/C25H26O12/c1-10-18(28)17-19(29)12(4-11-2-3-14-15(5-11)35-9-34-14)8-33-24(17)13(6-26)23(10)37-25-22(32)21(31)20(30)16(7-27)36-25/h2-3,5-6,12,16,20-22,25,27-28,30-32H,4,7-9H2,1H3/t12-,16+,20-,21-,22+,25-/m0/s1
• InChI Key: OBMSIXVTKJATDI-CVEKKARXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₆O₁₂
• Molecular Weight: 518.50 g/mol
• Exact Mass: 518.14242626 g/mol
• Topological Polar Surface Area (TPSA): 181.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): -0.15
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5417	54.17%
Caco-2	-	0.8806	88.06%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.6190	61.90%
OATP2B1 inhibitior	-	0.8478	84.78%
OATP1B1 inhibitior	+	0.8084	80.84%
OATP1B3 inhibitior	+	0.9711	97.11%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7421	74.21%
P-glycoprotein inhibitior	-	0.5705	57.05%
P-glycoprotein substrate	-	0.6093	60.93%
CYP3A4 substrate	+	0.6594	65.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8513	85.13%
CYP3A4 inhibition	-	0.7154	71.54%
CYP2C9 inhibition	-	0.8409	84.09%
CYP2C19 inhibition	-	0.7315	73.15%
CYP2D6 inhibition	-	0.9112	91.12%
CYP1A2 inhibition	-	0.8798	87.98%
CYP2C8 inhibition	+	0.5766	57.66%
CYP inhibitory promiscuity	-	0.6300	63.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5726	57.26%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9297	92.97%
Skin irritation	-	0.8278	82.78%
Skin corrosion	-	0.9448	94.48%
Ames mutagenesis	+	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4225	42.25%
Micronuclear	+	0.6333	63.33%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.8598	85.98%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.7983	79.83%
Acute Oral Toxicity (c)	III	0.6551	65.51%
Estrogen receptor binding	+	0.7895	78.95%
Androgen receptor binding	+	0.6733	67.33%
Thyroid receptor binding	-	0.5878	58.78%
Glucocorticoid receptor binding	+	0.5528	55.28%
Aromatase binding	-	0.5622	56.22%
PPAR gamma	+	0.5858	58.58%
Honey bee toxicity	-	0.7687	76.87%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8552	85.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.45%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.26%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.89%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.30%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.19%	96.77%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	96.67%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.79%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	93.77%	94.73%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	92.23%	83.57%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.73%	97.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.44%	94.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.86%	93.40%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.38%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	87.81%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.59%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.89%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.82%	86.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	85.44%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.63%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.27%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.17%	92.62%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.80%	96.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.08%	96.09%

Plants that contains it

• Ophiopogon japonicus

Cross-Links

• PubChem: 162966428
• LOTUS: LTS0061312
• wikiData: Q105189070