3,3'-Methylenebis[4-hydroxy-5,6-dimethyl-2H-pyran-2-one]

Details

• Internal ID: a4ce9bf4-13c9-402d-8e75-6928b992bedf
• Taxonomy: Organoheterocyclic compounds > Pyrans > Pyranones and derivatives
• IUPAC Name: 4-hydroxy-3-[(4-hydroxy-5,6-dimethyl-2-oxopyran-3-yl)methyl]-5,6-dimethylpyran-2-one
• SMILES (Canonical): CC1=C(OC(=O)C(=C1O)CC2=C(C(=C(OC2=O)C)C)O)C
• SMILES (Isomeric): CC1=C(OC(=O)C(=C1O)CC2=C(C(=C(OC2=O)C)C)O)C
• InChI: InChI=1S/C15H16O6/c1-6-8(3)20-14(18)10(12(6)16)5-11-13(17)7(2)9(4)21-15(11)19/h16-17H,5H2,1-4H3
• InChI Key: DATAFHMYYHJRSS-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₆
• Molecular Weight: 292.28 g/mol
• Exact Mass: 292.09468823 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.83
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 3,3'-Methylenebis[4-hydroxy-5,6-dimethyl-2H-pyran-2-one]
• COLLETOPYRONE
• 3,3'-Methylenebis(4-hydroxy-5,6-dimethyl-2H-pyran-2-one)
• NSC279558
• CHEMBL4571711
• DTXSID30715993
• FT-0774747

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8506	85.06%
Caco-2	+	0.5933	59.33%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8814	88.14%
OATP2B1 inhibitior	-	0.5715	57.15%
OATP1B1 inhibitior	-	0.4624	46.24%
OATP1B3 inhibitior	-	0.2452	24.52%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8870	88.70%
P-glycoprotein inhibitior	-	0.8722	87.22%
P-glycoprotein substrate	-	0.9797	97.97%
CYP3A4 substrate	-	0.6191	61.91%
CYP2C9 substrate	+	0.7031	70.31%
CYP2D6 substrate	-	0.8744	87.44%
CYP3A4 inhibition	-	0.9029	90.29%
CYP2C9 inhibition	+	0.5107	51.07%
CYP2C19 inhibition	-	0.8447	84.47%
CYP2D6 inhibition	-	0.9623	96.23%
CYP1A2 inhibition	-	0.8886	88.86%
CYP2C8 inhibition	-	0.9264	92.64%
CYP inhibitory promiscuity	-	0.8213	82.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8813	88.13%
Carcinogenicity (trinary)	Non-required	0.6492	64.92%
Eye corrosion	-	0.9889	98.89%
Eye irritation	+	0.6230	62.30%
Skin irritation	-	0.7952	79.52%
Skin corrosion	-	0.9636	96.36%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7012	70.12%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.6158	61.58%
skin sensitisation	-	0.8946	89.46%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.6519	65.19%
Acute Oral Toxicity (c)	III	0.5315	53.15%
Estrogen receptor binding	+	0.6196	61.96%
Androgen receptor binding	+	0.5735	57.35%
Thyroid receptor binding	-	0.5849	58.49%
Glucocorticoid receptor binding	+	0.5925	59.25%
Aromatase binding	-	0.6080	60.80%
PPAR gamma	+	0.6312	63.12%
Honey bee toxicity	-	0.9623	96.23%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9722	97.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	96.60%	89.34%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	91.47%	83.57%
CHEMBL3401	O75469	Pregnane X receptor	91.44%	94.73%
CHEMBL2581	P07339	Cathepsin D	89.76%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.98%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.54%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.56%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.98%	89.00%

Plants that contains it

• Helichrysum arenarium
• Helichrysum stoechas

Cross-Links

• PubChem: 54697221
• LOTUS: LTS0035260
• wikiData: Q82653372