(3aR,5R,5aR,9aR)-3a,5,9a-trihydroxy-1,5-dimethyl-8-methylidene-5a,6,7,9-tetrahydro-4H-benzo[e][1]benzofuran-2-one

Details

• Internal ID: 53e2aaa7-5f21-4b7f-ae79-9c72a04fd040
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (3aR,5R,5aR,9aR)-3a,5,9a-trihydroxy-1,5-dimethyl-8-methylidene-5a,6,7,9-tetrahydro-4H-benzo[e][1]benzofuran-2-one
• InChI: InChI=1S/C15H20O5/c1-8-4-5-10-13(3,17)7-15(19)11(14(10,18)6-8)9(2)12(16)20-15/h10,17-19H,1,4-7H2,2-3H3/t10-,13-,14-,15-/m1/s1
• InChI Key: RVQZLIFPBJHWSH-JUDXGUMMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 0.79
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9847	98.47%
Caco-2	+	0.5887	58.87%
Blood Brain Barrier	+	0.5027	50.27%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6829	68.29%
OATP2B1 inhibitior	-	0.8539	85.39%
OATP1B1 inhibitior	+	0.9193	91.93%
OATP1B3 inhibitior	+	0.8714	87.14%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5670	56.70%
BSEP inhibitior	-	0.9162	91.62%
P-glycoprotein inhibitior	-	0.9104	91.04%
P-glycoprotein substrate	-	0.8951	89.51%
CYP3A4 substrate	+	0.6121	61.21%
CYP2C9 substrate	-	0.8016	80.16%
CYP2D6 substrate	-	0.8657	86.57%
CYP3A4 inhibition	-	0.6226	62.26%
CYP2C9 inhibition	-	0.8991	89.91%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9407	94.07%
CYP1A2 inhibition	-	0.6988	69.88%
CYP2C8 inhibition	-	0.7853	78.53%
CYP inhibitory promiscuity	-	0.8863	88.63%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5028	50.28%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.7180	71.80%
Skin irritation	+	0.5979	59.79%
Skin corrosion	-	0.8997	89.97%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5936	59.36%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.5217	52.17%
skin sensitisation	-	0.7983	79.83%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	+	0.7010	70.10%
Acute Oral Toxicity (c)	I	0.4566	45.66%
Estrogen receptor binding	+	0.7019	70.19%
Androgen receptor binding	+	0.5302	53.02%
Thyroid receptor binding	+	0.7132	71.32%
Glucocorticoid receptor binding	+	0.5984	59.84%
Aromatase binding	+	0.6098	60.98%
PPAR gamma	-	0.4840	48.40%
Honey bee toxicity	-	0.9359	93.59%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9946	99.46%

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	95.38%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.76%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.90%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.48%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.79%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.04%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.96%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.31%	89.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	81.47%	93.03%

Plants that contains it

• Chloranthus serratus

Cross-Links

• PubChem: 57409961
• LOTUS: LTS0202858
• wikiData: Q105246246