(5S,5aS,9aS,9bS)-5,9b-dihydroxy-6,6,9a-trimethyl-1,5,5a,7,8,9-hexahydrobenzo[e][2]benzofuran-3-one

Details

• Internal ID: 9da06f0e-5b75-45ae-b4ff-7790803fefa9
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (5S,5aS,9aS,9bS)-5,9b-dihydroxy-6,6,9a-trimethyl-1,5,5a,7,8,9-hexahydrobenzo[e][2]benzofuran-3-one
• SMILES (Canonical): CC1(CCCC2(C1C(C=C3C2(COC3=O)O)O)C)C
• SMILES (Isomeric): C[C@]12CCCC([C@@H]1[C@H](C=C3[C@@]2(COC3=O)O)O)(C)C
• InChI: InChI=1S/C15H22O4/c1-13(2)5-4-6-14(3)11(13)10(16)7-9-12(17)19-8-15(9,14)18/h7,10-11,16,18H,4-6,8H2,1-3H3/t10-,11-,14-,15+/m0/s1
• InChI Key: HLEGAPKZEJEXHT-LWWSYDQCSA-N
• Popularity: 0 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: 1.60
• Atomic LogP (AlogP): 1.41
• 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	+	0.9925	99.25%
Caco-2	+	0.8964	89.64%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8505	85.05%
OATP2B1 inhibitior	-	0.8508	85.08%
OATP1B1 inhibitior	+	0.8711	87.11%
OATP1B3 inhibitior	+	0.9500	95.00%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	+	0.5458	54.58%
BSEP inhibitior	-	0.8085	80.85%
P-glycoprotein inhibitior	-	0.9381	93.81%
P-glycoprotein substrate	-	0.8689	86.89%
CYP3A4 substrate	+	0.5690	56.90%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.8809	88.09%
CYP3A4 inhibition	-	0.8087	80.87%
CYP2C9 inhibition	-	0.8146	81.46%
CYP2C19 inhibition	-	0.8970	89.70%
CYP2D6 inhibition	-	0.9384	93.84%
CYP1A2 inhibition	-	0.8059	80.59%
CYP2C8 inhibition	-	0.8702	87.02%
CYP inhibitory promiscuity	-	0.9184	91.84%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4347	43.47%
Eye corrosion	-	0.9914	99.14%
Eye irritation	-	0.8916	89.16%
Skin irritation	+	0.6296	62.96%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7997	79.97%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	+	0.6661	66.61%
skin sensitisation	-	0.8654	86.54%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	+	0.6399	63.99%
Acute Oral Toxicity (c)	III	0.5786	57.86%
Estrogen receptor binding	+	0.6331	63.31%
Androgen receptor binding	+	0.5817	58.17%
Thyroid receptor binding	-	0.5283	52.83%
Glucocorticoid receptor binding	-	0.5262	52.62%
Aromatase binding	+	0.5441	54.41%
PPAR gamma	-	0.5635	56.35%
Honey bee toxicity	-	0.9123	91.23%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9897	98.97%

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	96.52%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.23%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.78%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.69%	97.25%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.14%	82.69%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.55%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.87%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.93%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.87%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.67%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.48%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.31%	94.45%

Plants that contains it

• Cinnamosma madagascariensis

Cross-Links

• PubChem: 12771415
• LOTUS: LTS0235662
• wikiData: Q105030107