(4aS,8S,8aS,9aS)-8,9a-dihydroxy-3,4a,5-trimethyl-7,8,8a,9-tetrahydro-4H-benzo[f][1]benzofuran-2-one

Details

• Internal ID: 5a0515fe-2c76-49e6-a971-82dba2ff4e75
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (4aS,8S,8aS,9aS)-8,9a-dihydroxy-3,4a,5-trimethyl-7,8,8a,9-tetrahydro-4H-benzo[f][1]benzofuran-2-one
• SMILES (Canonical): CC1=CCC(C2C1(CC3=C(C(=O)OC3(C2)O)C)C)O
• SMILES (Isomeric): CC1=CC[C@@H]([C@@H]2[C@@]1(CC3=C(C(=O)O[C@]3(C2)O)C)C)O
• InChI: InChI=1S/C15H20O4/c1-8-4-5-12(16)11-7-15(18)10(6-14(8,11)3)9(2)13(17)19-15/h4,11-12,16,18H,5-7H2,1-3H3/t11-,12+,14-,15+/m1/s1
• InChI Key: GBAWDNPOGWZKDX-OSRDXIQISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.68
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9953	99.53%
Caco-2	+	0.7753	77.53%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.6788	67.88%
OATP2B1 inhibitior	-	0.8540	85.40%
OATP1B1 inhibitior	+	0.9247	92.47%
OATP1B3 inhibitior	+	0.9357	93.57%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6348	63.48%
P-glycoprotein inhibitior	-	0.9403	94.03%
P-glycoprotein substrate	-	0.8740	87.40%
CYP3A4 substrate	+	0.6096	60.96%
CYP2C9 substrate	-	0.7943	79.43%
CYP2D6 substrate	-	0.8686	86.86%
CYP3A4 inhibition	-	0.6613	66.13%
CYP2C9 inhibition	-	0.9066	90.66%
CYP2C19 inhibition	-	0.9044	90.44%
CYP2D6 inhibition	-	0.9627	96.27%
CYP1A2 inhibition	-	0.7717	77.17%
CYP2C8 inhibition	-	0.8925	89.25%
CYP inhibitory promiscuity	-	0.8869	88.69%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4074	40.74%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.9381	93.81%
Skin irritation	+	0.6272	62.72%
Skin corrosion	-	0.9301	93.01%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6291	62.91%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.5408	54.08%
skin sensitisation	-	0.7776	77.76%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9500	95.00%
Nephrotoxicity	+	0.7145	71.45%
Acute Oral Toxicity (c)	I	0.5983	59.83%
Estrogen receptor binding	-	0.7706	77.06%
Androgen receptor binding	+	0.5625	56.25%
Thyroid receptor binding	+	0.5415	54.15%
Glucocorticoid receptor binding	-	0.4734	47.34%
Aromatase binding	-	0.5861	58.61%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.8872	88.72%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9941	99.41%

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	96.93%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.57%	95.56%
CHEMBL2581	P07339	Cathepsin D	90.39%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.25%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.82%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.81%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	84.63%	94.73%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.25%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.37%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.92%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.67%	97.09%
CHEMBL4208	P20618	Proteasome component C5	82.14%	90.00%
CHEMBL1937	Q92769	Histone deacetylase 2	82.07%	94.75%

Plants that contains it

• Smyrnium connatum
• Smyrnium creticum

Cross-Links

• PubChem: 162912463
• LOTUS: LTS0160737
• wikiData: Q105005742