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

Details

• Internal ID: dedb42e2-7f8d-40ff-84c8-257431b87031
• Taxonomy: Phenylpropanoids and polyketides > Homoisoflavonoids > Homoisoflavans
• IUPAC Name: (3S)-3,5,7-trihydroxy-3-[(4-hydroxyphenyl)methyl]-8-methoxy-6-methyl-2H-chromen-4-one
• SMILES (Canonical): CC1=C(C2=C(C(=C1O)OC)OCC(C2=O)(CC3=CC=C(C=C3)O)O)O
• SMILES (Isomeric): CC1=C(C2=C(C(=C1O)OC)OC[C@](C2=O)(CC3=CC=C(C=C3)O)O)O
• InChI: InChI=1S/C18H18O7/c1-9-13(20)12-15(16(24-2)14(9)21)25-8-18(23,17(12)22)7-10-3-5-11(19)6-4-10/h3-6,19-21,23H,7-8H2,1-2H3/t18-/m0/s1
• InChI Key: KJLKHEXGKXUNTN-SFHVURJKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₈O₇
• Molecular Weight: 346.30 g/mol
• Exact Mass: 346.10525291 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 1.67
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

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

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9320	93.20%
Caco-2	+	0.5573	55.73%
Blood Brain Barrier	-	0.6895	68.95%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6090	60.90%
OATP2B1 inhibitior	-	0.5681	56.81%
OATP1B1 inhibitior	+	0.8642	86.42%
OATP1B3 inhibitior	+	0.8823	88.23%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5856	58.56%
P-glycoprotein inhibitior	-	0.7320	73.20%
P-glycoprotein substrate	-	0.7345	73.45%
CYP3A4 substrate	+	0.5745	57.45%
CYP2C9 substrate	-	0.8052	80.52%
CYP2D6 substrate	-	0.7823	78.23%
CYP3A4 inhibition	-	0.5222	52.22%
CYP2C9 inhibition	-	0.7906	79.06%
CYP2C19 inhibition	-	0.5952	59.52%
CYP2D6 inhibition	-	0.7138	71.38%
CYP1A2 inhibition	+	0.5751	57.51%
CYP2C8 inhibition	+	0.5859	58.59%
CYP inhibitory promiscuity	-	0.5896	58.96%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6928	69.28%
Eye corrosion	-	0.9857	98.57%
Eye irritation	+	0.7328	73.28%
Skin irritation	-	0.8005	80.05%
Skin corrosion	-	0.9509	95.09%
Ames mutagenesis	-	0.6054	60.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6645	66.45%
Micronuclear	+	0.6818	68.18%
Hepatotoxicity	+	0.5855	58.55%
skin sensitisation	-	0.8367	83.67%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6580	65.80%
Acute Oral Toxicity (c)	III	0.6897	68.97%
Estrogen receptor binding	+	0.9334	93.34%
Androgen receptor binding	+	0.6729	67.29%
Thyroid receptor binding	+	0.6914	69.14%
Glucocorticoid receptor binding	+	0.7386	73.86%
Aromatase binding	+	0.5512	55.12%
PPAR gamma	+	0.6668	66.68%
Honey bee toxicity	-	0.8744	87.44%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	-	0.4127	41.27%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.03%	94.45%
CHEMBL2581	P07339	Cathepsin D	96.66%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.30%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.77%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.73%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.40%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.59%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.51%	95.89%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.54%	90.93%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.37%	97.28%
CHEMBL4208	P20618	Proteasome component C5	81.86%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.37%	99.17%

Plants that contains it

• Polygonatum odoratum

Cross-Links

• PubChem: 71625779
• NPASS: NPC290205