(3R)-15-hydroxy-3,7,7-trimethyl-13-propan-2-yl-4-oxatricyclo[9.4.0.03,8]pentadeca-1(15),8,10,12-tetraene-5,14-dione

Details

• Internal ID: 5dc908e6-b162-41ea-a8b7-30289fc8da48
• Taxonomy: Organoheterocyclic compounds > Lactones > Delta valerolactones
• IUPAC Name: (3R)-15-hydroxy-3,7,7-trimethyl-13-propan-2-yl-4-oxatricyclo[9.4.0.03,8]pentadeca-1(15),8,10,12-tetraene-5,14-dione
• SMILES (Canonical): CC(C)C1=CC2=CC=C3C(CC(=O)OC3(CC2=C(C1=O)O)C)(C)C
• SMILES (Isomeric): CC(C)C1=CC2=CC=C3[C@@](CC2=C(C1=O)O)(OC(=O)CC3(C)C)C
• InChI: InChI=1S/C20H24O4/c1-11(2)13-8-12-6-7-15-19(3,4)10-16(21)24-20(15,5)9-14(12)18(23)17(13)22/h6-8,11,23H,9-10H2,1-5H3/t20-/m1/s1
• InChI Key: HMJSIJZITOCLAD-HXUWFJFHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₄
• Molecular Weight: 328.40 g/mol
• Exact Mass: 328.16745924 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 3.95
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9823	98.23%
Caco-2	+	0.6112	61.12%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7852	78.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8843	88.43%
OATP1B3 inhibitior	+	0.9149	91.49%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.7144	71.44%
P-glycoprotein inhibitior	-	0.7841	78.41%
P-glycoprotein substrate	-	0.7502	75.02%
CYP3A4 substrate	+	0.5684	56.84%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9024	90.24%
CYP3A4 inhibition	-	0.8322	83.22%
CYP2C9 inhibition	-	0.8399	83.99%
CYP2C19 inhibition	-	0.8721	87.21%
CYP2D6 inhibition	-	0.9451	94.51%
CYP1A2 inhibition	-	0.8991	89.91%
CYP2C8 inhibition	-	0.8786	87.86%
CYP inhibitory promiscuity	-	0.9535	95.35%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5802	58.02%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.8802	88.02%
Skin irritation	-	0.6066	60.66%
Skin corrosion	-	0.9265	92.65%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7259	72.59%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.5502	55.02%
skin sensitisation	-	0.6413	64.13%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6139	61.39%
Acute Oral Toxicity (c)	III	0.6124	61.24%
Estrogen receptor binding	+	0.8329	83.29%
Androgen receptor binding	+	0.5637	56.37%
Thyroid receptor binding	+	0.6920	69.20%
Glucocorticoid receptor binding	+	0.7418	74.18%
Aromatase binding	+	0.7054	70.54%
PPAR gamma	+	0.8069	80.69%
Honey bee toxicity	-	0.7173	71.73%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9724	97.24%

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	97.56%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.23%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.98%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.34%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.93%	99.23%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	88.66%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.17%	89.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.54%	90.71%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	85.54%	93.40%
CHEMBL3401	O75469	Pregnane X receptor	83.53%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.93%	96.09%

Plants that contains it

• Premna herbacea

Cross-Links

• PubChem: 53364007
• LOTUS: LTS0031150
• wikiData: Q105030539