(3R)-3-hydroxy-2,2-dimethyl-7-(2-methylbut-3-en-2-yl)-3,4-dihydropyrano[3,2-g]chromen-8-one

Details

• Internal ID: e2afa74b-8fa4-4798-b25d-232d80adde9f
• Taxonomy: Phenylpropanoids and polyketides > Coumarins and derivatives > Pyranocoumarins > Linear pyranocoumarins
• IUPAC Name: (3R)-3-hydroxy-2,2-dimethyl-7-(2-methylbut-3-en-2-yl)-3,4-dihydropyrano[3,2-g]chromen-8-one
• SMILES (Canonical): CC1(C(CC2=C(O1)C=C3C(=C2)C=C(C(=O)O3)C(C)(C)C=C)O)C
• SMILES (Isomeric): CC1([C@@H](CC2=C(O1)C=C3C(=C2)C=C(C(=O)O3)C(C)(C)C=C)O)C
• InChI: InChI=1S/C19H22O4/c1-6-18(2,3)13-8-11-7-12-9-16(20)19(4,5)23-15(12)10-14(11)22-17(13)21/h6-8,10,16,20H,1,9H2,2-5H3/t16-/m1/s1
• InChI Key: GXNOBSWJKBHASE-MRXNPFEDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₉H₂₂O₄
• Molecular Weight: 314.40 g/mol
• Exact Mass: 314.15180918 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 3.33
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9887	98.87%
Caco-2	+	0.6218	62.18%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.6111	61.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8808	88.08%
OATP1B3 inhibitior	+	0.9505	95.05%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.4928	49.28%
P-glycoprotein inhibitior	-	0.7810	78.10%
P-glycoprotein substrate	-	0.6487	64.87%
CYP3A4 substrate	+	0.5782	57.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8001	80.01%
CYP3A4 inhibition	-	0.6688	66.88%
CYP2C9 inhibition	-	0.9462	94.62%
CYP2C19 inhibition	-	0.8734	87.34%
CYP2D6 inhibition	-	0.8788	87.88%
CYP1A2 inhibition	-	0.7506	75.06%
CYP2C8 inhibition	-	0.7522	75.22%
CYP inhibitory promiscuity	-	0.9401	94.01%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5296	52.96%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.7065	70.65%
Skin irritation	-	0.6453	64.53%
Skin corrosion	-	0.9113	91.13%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3810	38.10%
Micronuclear	+	0.5018	50.18%
Hepatotoxicity	-	0.6197	61.97%
skin sensitisation	-	0.6589	65.89%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.4654	46.54%
Acute Oral Toxicity (c)	III	0.6215	62.15%
Estrogen receptor binding	+	0.8847	88.47%
Androgen receptor binding	+	0.5521	55.21%
Thyroid receptor binding	+	0.7337	73.37%
Glucocorticoid receptor binding	+	0.6232	62.32%
Aromatase binding	+	0.8127	81.27%
PPAR gamma	+	0.8277	82.77%
Honey bee toxicity	-	0.8236	82.36%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9871	98.71%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.62%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.40%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.20%	85.14%
CHEMBL2581	P07339	Cathepsin D	96.11%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.28%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.18%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.86%	97.25%
CHEMBL3401	O75469	Pregnane X receptor	89.13%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.88%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.79%	89.34%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.07%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	84.90%	90.71%
CHEMBL5408	Q9UHD2	Serine/threonine-protein kinase TBK1	83.41%	90.48%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.90%	94.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.19%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.17%	89.00%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	82.15%	80.00%
CHEMBL1937	Q92769	Histone deacetylase 2	81.77%	94.75%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.00%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.90%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.28%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.09%	94.45%

Plants that contains it

• Aeollanthus buchnerianus
• Cynoglossum viridiflorum
• Echium plantagineum
• Helianthus niveus
• Helietta apiculata
• Hernandia sonora
• Leptospermum recurvum

Cross-Links

• PubChem: 92470573
• NPASS: NPC99751
• LOTUS: LTS0267805
• wikiData: Q105023225