(3S)-3,5,7-trihydroxy-3-[(4-hydroxyphenyl)methyl]-6,8-dimethyl-2H-chromen-4-one

Details

• Internal ID: c39ab1b9-59f5-41e2-99bc-032c651ee0ff
• Taxonomy: Phenylpropanoids and polyketides > Homoisoflavonoids > Homoisoflavans
• IUPAC Name: (3S)-3,5,7-trihydroxy-3-[(4-hydroxyphenyl)methyl]-6,8-dimethyl-2H-chromen-4-one
• SMILES (Canonical): CC1=C(C(=C2C(=C1O)C(=O)C(CO2)(CC3=CC=C(C=C3)O)O)C)O
• SMILES (Isomeric): CC1=C(C(=C2C(=C1O)C(=O)[C@@](CO2)(CC3=CC=C(C=C3)O)O)C)O
• InChI: InChI=1S/C18H18O6/c1-9-14(20)10(2)16-13(15(9)21)17(22)18(23,8-24-16)7-11-3-5-12(19)6-4-11/h3-6,19-21,23H,7-8H2,1-2H3/t18-/m0/s1
• InChI Key: TUXGIPNQUYTUBE-SFHVURJKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈O₆
• Molecular Weight: 330.30 g/mol
• Exact Mass: 330.11033829 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 1.97
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• (3S)-3,5,7-Trihydroxy-3-(4-hydroxybenzyl)-6,8-dimethyl-2,3-dihydro-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9350	93.50%
Caco-2	-	0.5152	51.52%
Blood Brain Barrier	-	0.6395	63.95%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6244	62.44%
OATP2B1 inhibitior	+	0.5699	56.99%
OATP1B1 inhibitior	+	0.8183	81.83%
OATP1B3 inhibitior	+	0.8898	88.98%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.6581	65.81%
P-glycoprotein inhibitior	-	0.7628	76.28%
P-glycoprotein substrate	-	0.7618	76.18%
CYP3A4 substrate	+	0.5196	51.96%
CYP2C9 substrate	-	0.8052	80.52%
CYP2D6 substrate	-	0.7823	78.23%
CYP3A4 inhibition	-	0.6938	69.38%
CYP2C9 inhibition	-	0.7737	77.37%
CYP2C19 inhibition	-	0.7882	78.82%
CYP2D6 inhibition	-	0.8901	89.01%
CYP1A2 inhibition	+	0.6821	68.21%
CYP2C8 inhibition	+	0.5485	54.85%
CYP inhibitory promiscuity	-	0.6750	67.50%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6782	67.82%
Eye corrosion	-	0.9913	99.13%
Eye irritation	+	0.8720	87.20%
Skin irritation	-	0.7698	76.98%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7844	78.44%
Micronuclear	+	0.6159	61.59%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.7657	76.57%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.5826	58.26%
Acute Oral Toxicity (c)	III	0.6372	63.72%
Estrogen receptor binding	+	0.8670	86.70%
Androgen receptor binding	+	0.7316	73.16%
Thyroid receptor binding	+	0.6700	67.00%
Glucocorticoid receptor binding	+	0.7920	79.20%
Aromatase binding	+	0.6030	60.30%
PPAR gamma	+	0.7172	71.72%
Honey bee toxicity	-	0.9193	91.93%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.7203	72.03%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	97.83%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.78%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.42%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.32%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.10%	94.00%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	88.41%	90.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.69%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.36%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.75%	96.09%
CHEMBL4208	P20618	Proteasome component C5	82.38%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.66%	86.33%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.08%	93.10%

Plants that contains it

• Polygonatum odoratum

Cross-Links

• PubChem: 71625780
• NPASS: NPC156917