1,9b-Dihydroxy-6,6,9a-trimethyl-1,5,5a,7,8,9-hexahydrobenzo[e][2]benzofuran-3-one

Details

• Internal ID: 3b197700-632b-4604-9de7-cfbb02f1a00e
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: 1,9b-dihydroxy-6,6,9a-trimethyl-1,5,5a,7,8,9-hexahydrobenzo[e][2]benzofuran-3-one
• SMILES (Canonical): CC1(CCCC2(C1CC=C3C2(C(OC3=O)O)O)C)C
• SMILES (Isomeric): CC1(CCCC2(C1CC=C3C2(C(OC3=O)O)O)C)C
• InChI: InChI=1S/C15H22O4/c1-13(2)7-4-8-14(3)10(13)6-5-9-11(16)19-12(17)15(9,14)18/h5,10,12,17-18H,4,6-8H2,1-3H3
• InChI Key: XLGNZQXMDVSKOV-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: 2.20
• Atomic LogP (AlogP): 1.76
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• Compound NP-015072
• CHEBI:181275
• AKOS040738808
• NCGC00380941-01
• 1,9b-dihydroxy-6,6,9a-trimethyl-1,5,5a,7,8,9-hexahydrobenzo[e][2]benzouran-3-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9840	98.40%
Caco-2	+	0.7915	79.15%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7641	76.41%
OATP2B1 inhibitior	-	0.8538	85.38%
OATP1B1 inhibitior	+	0.8724	87.24%
OATP1B3 inhibitior	+	0.8525	85.25%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5821	58.21%
BSEP inhibitior	-	0.8354	83.54%
P-glycoprotein inhibitior	-	0.9350	93.50%
P-glycoprotein substrate	-	0.9319	93.19%
CYP3A4 substrate	+	0.5681	56.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8786	87.86%
CYP3A4 inhibition	-	0.7228	72.28%
CYP2C9 inhibition	-	0.6878	68.78%
CYP2C19 inhibition	-	0.7223	72.23%
CYP2D6 inhibition	-	0.9237	92.37%
CYP1A2 inhibition	+	0.5324	53.24%
CYP2C8 inhibition	-	0.8517	85.17%
CYP inhibitory promiscuity	-	0.8353	83.53%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4877	48.77%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9233	92.33%
Skin irritation	+	0.5596	55.96%
Skin corrosion	-	0.9231	92.31%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8146	81.46%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.6233	62.33%
skin sensitisation	-	0.7214	72.14%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.4244	42.44%
Estrogen receptor binding	+	0.6225	62.25%
Androgen receptor binding	+	0.5772	57.72%
Thyroid receptor binding	+	0.5433	54.33%
Glucocorticoid receptor binding	-	0.5646	56.46%
Aromatase binding	+	0.5455	54.55%
PPAR gamma	-	0.5640	56.40%
Honey bee toxicity	-	0.9147	91.47%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	94.99%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.51%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.25%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.52%	82.69%
CHEMBL2581	P07339	Cathepsin D	88.40%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.07%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.93%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.90%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.48%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.89%	89.00%
CHEMBL1937	Q92769	Histone deacetylase 2	80.53%	94.75%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.29%	86.33%

Plants that contains it

• Warburgia ugandensis

Cross-Links

• PubChem: 45783128
• LOTUS: LTS0168206
• wikiData: Q105329963