(3R,6S,7S)-3-Butyl-6,7-dihydroxy-4,5,6,7-tetrahydroisobenzofuran-1(3H)-one

Details

• Internal ID: 3a664c8b-2403-4e74-a0f9-c752cc32fa87
• Taxonomy: Organoheterocyclic compounds > Isobenzofurans
• IUPAC Name: 3-butyl-6,7-dihydroxy-4,5,6,7-tetrahydro-3H-2-benzofuran-1-one
• SMILES (Canonical): CCCCC1C2=C(C(C(CC2)O)O)C(=O)O1
• SMILES (Isomeric): CCCCC1C2=C(C(C(CC2)O)O)C(=O)O1
• InChI: InChI=1S/C12H18O4/c1-2-3-4-9-7-5-6-8(13)11(14)10(7)12(15)16-9/h8-9,11,13-14H,2-6H2,1H3
• InChI Key: AXRIHSJZHOTGAE-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₈O₄
• Molecular Weight: 226.27 g/mol
• Exact Mass: 226.12050905 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.91
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• MEGxp0_001263
• AXRIHSJZHOTGAE-UHFFFAOYSA-N
• (3R,6S,7S)-3-Butyl-6,7-dihydroxy-4,5,6,7-tetrahydroisobenzofuran-1(3H)-one
• 1(3H)-Isobenzofuranone, 3-butyl-4,5,6,7-tetrahydro-6,7-dihydroxy-, (3R,6S,7S)-
• 1(3H)-Isobenzofuranone, 3-butyl-4,5,6,7-tetrahydro-6,7-dihydroxy-, [3R-(3.alpha.,6.alpha.,7.beta.)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9866	98.66%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6514	65.14%
OATP2B1 inhibitior	-	0.8492	84.92%
OATP1B1 inhibitior	+	0.8984	89.84%
OATP1B3 inhibitior	+	0.9635	96.35%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9297	92.97%
P-glycoprotein inhibitior	-	0.9512	95.12%
P-glycoprotein substrate	-	0.8580	85.80%
CYP3A4 substrate	-	0.5053	50.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8616	86.16%
CYP3A4 inhibition	-	0.6733	67.33%
CYP2C9 inhibition	-	0.8544	85.44%
CYP2C19 inhibition	-	0.6422	64.22%
CYP2D6 inhibition	-	0.8872	88.72%
CYP1A2 inhibition	-	0.6401	64.01%
CYP2C8 inhibition	-	0.9094	90.94%
CYP inhibitory promiscuity	-	0.8809	88.09%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5710	57.10%
Eye corrosion	-	0.9830	98.30%
Eye irritation	-	0.7992	79.92%
Skin irritation	+	0.4924	49.24%
Skin corrosion	-	0.9177	91.77%
Ames mutagenesis	-	0.7437	74.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6339	63.39%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.5571	55.71%
skin sensitisation	-	0.8091	80.91%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.4812	48.12%
Acute Oral Toxicity (c)	II	0.3646	36.46%
Estrogen receptor binding	-	0.7039	70.39%
Androgen receptor binding	-	0.5717	57.17%
Thyroid receptor binding	+	0.5449	54.49%
Glucocorticoid receptor binding	-	0.4825	48.25%
Aromatase binding	-	0.9063	90.63%
PPAR gamma	-	0.5878	58.78%
Honey bee toxicity	-	0.9783	97.83%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9852	98.52%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	95.56%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.46%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	92.78%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.85%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.15%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.89%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.93%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.45%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.95%	99.17%

Plants that contains it

• Apium graveolens
• Conioselinum anthriscoides
• Levisticum officinale
• Ligusticum officinale

Cross-Links

• PubChem: 24121290
• NPASS: NPC85013
• LOTUS: LTS0035215
• wikiData: Q104399093