(3S,5aS,8R,9S,9aS,9bS)-8,9-dihydroxy-3,5a,9-trimethyl-5,6,7,8,9a,9b-hexahydro-3H-benzo[g][1]benzofuran-2-one

Details

• Internal ID: 53c259ef-c7dc-4f0e-94e8-7b21119a5080
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: (3S,5aS,8R,9S,9aS,9bS)-8,9-dihydroxy-3,5a,9-trimethyl-5,6,7,8,9a,9b-hexahydro-3H-benzo[g][1]benzofuran-2-one
• SMILES (Canonical): CC1C2=CCC3(CCC(C(C3C2OC1=O)(C)O)O)C
• SMILES (Isomeric): C[C@H]1C2=CC[C@@]3(CC[C@H]([C@@]([C@@H]3[C@@H]2OC1=O)(C)O)O)C
• InChI: InChI=1S/C15H22O4/c1-8-9-4-6-14(2)7-5-10(16)15(3,18)12(14)11(9)19-13(8)17/h4,8,10-12,16,18H,5-7H2,1-3H3/t8-,10+,11+,12+,14+,15+/m0/s1
• InChI Key: WQBRGPAKTOXTFK-YZUDAQNMSA-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: 1.00
• 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	+	0.9833	98.33%
Caco-2	-	0.5394	53.94%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7165	71.65%
OATP2B1 inhibitior	-	0.8563	85.63%
OATP1B1 inhibitior	+	0.9392	93.92%
OATP1B3 inhibitior	+	0.9372	93.72%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6821	68.21%
BSEP inhibitior	-	0.9440	94.40%
P-glycoprotein inhibitior	-	0.9085	90.85%
P-glycoprotein substrate	-	0.8341	83.41%
CYP3A4 substrate	+	0.5837	58.37%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8583	85.83%
CYP3A4 inhibition	-	0.6532	65.32%
CYP2C9 inhibition	-	0.8514	85.14%
CYP2C19 inhibition	-	0.8144	81.44%
CYP2D6 inhibition	-	0.9356	93.56%
CYP1A2 inhibition	-	0.6165	61.65%
CYP2C8 inhibition	-	0.9356	93.56%
CYP inhibitory promiscuity	-	0.9297	92.97%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.4032	40.32%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9751	97.51%
Skin irritation	+	0.6786	67.86%
Skin corrosion	-	0.8818	88.18%
Ames mutagenesis	-	0.7870	78.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.7038	70.38%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.6500	65.00%
skin sensitisation	-	0.8253	82.53%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.9250	92.50%
Nephrotoxicity	+	0.6420	64.20%
Acute Oral Toxicity (c)	III	0.3453	34.53%
Estrogen receptor binding	+	0.5828	58.28%
Androgen receptor binding	-	0.5000	50.00%
Thyroid receptor binding	+	0.6484	64.84%
Glucocorticoid receptor binding	+	0.6041	60.41%
Aromatase binding	-	0.6786	67.86%
PPAR gamma	-	0.6786	67.86%
Honey bee toxicity	-	0.9008	90.08%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9801	98.01%

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	91.30%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.26%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.54%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.36%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.94%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.15%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.23%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.25%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.90%	89.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.32%	93.04%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.79%	93.03%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	80.49%	90.24%

Plants that contains it

• Seriphidium tenuisectum

Cross-Links

• PubChem: 162973798
• LOTUS: LTS0212991
• wikiData: Q105310319