5,7-Dihydroxy-6-[(2-hydroxyphenyl)methyl]-2-phenyl-2,3-dihydrochromen-4-one

Details

• Internal ID: dbec26d4-9148-4bbe-bc4a-8e4b7907bcd5
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: 5,7-dihydroxy-6-[(2-hydroxyphenyl)methyl]-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): C1C(OC2=C(C1=O)C(=C(C(=C2)O)CC3=CC=CC=C3O)O)C4=CC=CC=C4
• SMILES (Isomeric): C1C(OC2=C(C1=O)C(=C(C(=C2)O)CC3=CC=CC=C3O)O)C4=CC=CC=C4
• InChI: InChI=1S/C22H18O5/c23-16-9-5-4-8-14(16)10-15-17(24)11-20-21(22(15)26)18(25)12-19(27-20)13-6-2-1-3-7-13/h1-9,11,19,23-24,26H,10,12H2
• InChI Key: KSBALECVCJXYHU-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₁₈O₅
• Molecular Weight: 362.40 g/mol
• Exact Mass: 362.11542367 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.10
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9130	91.30%
Caco-2	-	0.8029	80.29%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7686	76.86%
OATP2B1 inhibitior	-	0.5831	58.31%
OATP1B1 inhibitior	+	0.8953	89.53%
OATP1B3 inhibitior	-	0.3025	30.25%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.6842	68.42%
P-glycoprotein inhibitior	-	0.4476	44.76%
P-glycoprotein substrate	-	0.8811	88.11%
CYP3A4 substrate	-	0.5142	51.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7429	74.29%
CYP3A4 inhibition	+	0.6558	65.58%
CYP2C9 inhibition	+	0.8097	80.97%
CYP2C19 inhibition	+	0.8177	81.77%
CYP2D6 inhibition	-	0.8657	86.57%
CYP1A2 inhibition	+	0.6017	60.17%
CYP2C8 inhibition	+	0.5343	53.43%
CYP inhibitory promiscuity	+	0.6897	68.97%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6514	65.14%
Eye corrosion	-	0.9931	99.31%
Eye irritation	+	0.6210	62.10%
Skin irritation	-	0.5990	59.90%
Skin corrosion	-	0.9610	96.10%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6443	64.43%
Micronuclear	+	0.8159	81.59%
Hepatotoxicity	-	0.5842	58.42%
skin sensitisation	-	0.8406	84.06%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.7549	75.49%
Acute Oral Toxicity (c)	II	0.3843	38.43%
Estrogen receptor binding	+	0.8423	84.23%
Androgen receptor binding	+	0.6709	67.09%
Thyroid receptor binding	-	0.4928	49.28%
Glucocorticoid receptor binding	+	0.7308	73.08%
Aromatase binding	+	0.6085	60.85%
PPAR gamma	+	0.8499	84.99%
Honey bee toxicity	-	0.8563	85.63%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.8699	86.99%

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	99.62%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.96%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.24%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.00%	99.15%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.01%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.64%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.47%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.07%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	84.36%	93.99%
CHEMBL3401	O75469	Pregnane X receptor	83.49%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.17%	96.09%

Plants that contains it

• Piper sarmentosum
• Stellera chamaejasme
• Uvaria chamae
• Uvaria lucida

Cross-Links

• PubChem: 21721817
• NPASS: NPC102166
• LOTUS: LTS0187148
• wikiData: Q105145337