3a,8-dihydroxy-3,5a,9-trimethyl-4,5,6,7,8,9b-hexahydro-3H-benzo[g][1]benzofuran-2-one

Details

• Internal ID: 49fbc4df-e3f4-4713-8cf5-d452f436dfe8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
• IUPAC Name: 3a,8-dihydroxy-3,5a,9-trimethyl-4,5,6,7,8,9b-hexahydro-3H-benzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1C(=O)OC2C1(CCC3(C2=C(C(CC3)O)C)C)O
• SMILES (Isomeric): CC1C(=O)OC2C1(CCC3(C2=C(C(CC3)O)C)C)O
• InChI: InChI=1S/C15H22O4/c1-8-10(16)4-5-14(3)6-7-15(18)9(2)13(17)19-12(15)11(8)14/h9-10,12,16,18H,4-7H2,1-3H3
• InChI Key: NVXJDQXVTHYURW-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 1.55
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• SCHEMBL10076528
• CHEBI:181483
• AKOS040738416
• NCGC00384597-02
• 3a,8-dihydroxy-3,5a,9-trimethyl-4,5,6,7,8,9b-hexahydro-3H-benzo[g][1]benzofuran-2-one
• 3a,8-dihydroxy-3,5a,9-trimethyl-4,5,6,7,8,9b-hexahydro-3H-benzo[g][1]benzouran-2-one
• NCGC00384597-01!3a,8-dihydroxy-3,5a,9-trimethyl-4,5,6,7,8,9b-hexahydro-3H-benzo[g][1]benzofuran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9948	99.48%
Caco-2	+	0.8036	80.36%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7017	70.17%
OATP2B1 inhibitior	-	0.8522	85.22%
OATP1B1 inhibitior	+	0.9249	92.49%
OATP1B3 inhibitior	+	0.9398	93.98%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	-	0.9425	94.25%
P-glycoprotein inhibitior	-	0.9290	92.90%
P-glycoprotein substrate	-	0.8390	83.90%
CYP3A4 substrate	+	0.5680	56.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8595	85.95%
CYP3A4 inhibition	-	0.6753	67.53%
CYP2C9 inhibition	-	0.9053	90.53%
CYP2C19 inhibition	-	0.9218	92.18%
CYP2D6 inhibition	-	0.9571	95.71%
CYP1A2 inhibition	-	0.7030	70.30%
CYP2C8 inhibition	-	0.9380	93.80%
CYP inhibitory promiscuity	-	0.9464	94.64%
UGT catelyzed	+	0.6362	63.62%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4314	43.14%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.8695	86.95%
Skin irritation	+	0.6846	68.46%
Skin corrosion	-	0.9140	91.40%
Ames mutagenesis	-	0.6854	68.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.7010	70.10%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.5493	54.93%
skin sensitisation	-	0.8247	82.47%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.5377	53.77%
Acute Oral Toxicity (c)	IV	0.4051	40.51%
Estrogen receptor binding	-	0.6076	60.76%
Androgen receptor binding	+	0.5721	57.21%
Thyroid receptor binding	+	0.5698	56.98%
Glucocorticoid receptor binding	+	0.5394	53.94%
Aromatase binding	-	0.6426	64.26%
PPAR gamma	-	0.7198	71.98%
Honey bee toxicity	-	0.8609	86.09%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9866	98.66%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.80%	95.56%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.42%	96.38%
CHEMBL2581	P07339	Cathepsin D	83.60%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.33%	96.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.31%	93.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.15%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.13%	86.33%

Plants that contains it

• Grangea maderaspatana
• Sphaeranthus indicus

Cross-Links

• PubChem: 14312974
• LOTUS: LTS0043200
• wikiData: Q105186467