(3aS,4R,7aS)-3a,4-dihydroxy-2,3,4,5,7,7a-hexahydro-1-benzofuran-6-one

Details

• Internal ID: 13bd9958-f47b-4c27-9690-382a96fc1847
• Taxonomy: Organoheterocyclic compounds > Benzofurans
• IUPAC Name: (3aS,4R,7aS)-3a,4-dihydroxy-2,3,4,5,7,7a-hexahydro-1-benzofuran-6-one
• SMILES (Canonical): C1COC2C1(C(CC(=O)C2)O)O
• SMILES (Isomeric): C1CO[C@@H]2[C@]1([C@@H](CC(=O)C2)O)O
• InChI: InChI=1S/C8H12O4/c9-5-3-6(10)8(11)1-2-12-7(8)4-5/h6-7,10-11H,1-4H2/t6-,7+,8+/m1/s1
• InChI Key: DDRIMXADTYBMJR-CSMHCCOUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18 g/mol
• Exact Mass: 172.07355886 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -0.77
• 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	+	0.9509	95.09%
Caco-2	-	0.6787	67.87%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7910	79.10%
OATP2B1 inhibitior	-	0.8527	85.27%
OATP1B1 inhibitior	+	0.9645	96.45%
OATP1B3 inhibitior	+	0.9706	97.06%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8542	85.42%
BSEP inhibitior	-	0.9587	95.87%
P-glycoprotein inhibitior	-	0.9718	97.18%
P-glycoprotein substrate	-	0.9454	94.54%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7743	77.43%
CYP3A4 inhibition	-	0.9687	96.87%
CYP2C9 inhibition	-	0.9185	91.85%
CYP2C19 inhibition	-	0.8622	86.22%
CYP2D6 inhibition	-	0.9442	94.42%
CYP1A2 inhibition	-	0.8456	84.56%
CYP2C8 inhibition	-	0.9642	96.42%
CYP inhibitory promiscuity	-	0.9888	98.88%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5687	56.87%
Eye corrosion	-	0.9731	97.31%
Eye irritation	+	0.9307	93.07%
Skin irritation	-	0.7287	72.87%
Skin corrosion	-	0.9154	91.54%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7990	79.90%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.6577	65.77%
skin sensitisation	-	0.8832	88.32%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.5955	59.55%
Acute Oral Toxicity (c)	III	0.4571	45.71%
Estrogen receptor binding	-	0.7284	72.84%
Androgen receptor binding	-	0.7510	75.10%
Thyroid receptor binding	-	0.8006	80.06%
Glucocorticoid receptor binding	-	0.7331	73.31%
Aromatase binding	-	0.8252	82.52%
PPAR gamma	-	0.6222	62.22%
Honey bee toxicity	-	0.7387	73.87%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	-	0.5600	56.00%

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	89.59%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.28%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.28%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.19%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.93%	94.45%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.72%	85.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.56%	92.94%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.20%	90.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.99%	100.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	80.00%	93.03%

Plants that contains it

• Barleria acanthoides
• Clerodendrum indicum
• Cordia elaeagnoides
• Dodonaea viscosa
• Hexalobus crispiflorus
• Isodon leucophyllus
• Marrubium globosum
• Melicope lunu-ankenda
• Pyrus pyrifolia
• Tsuga heterophylla
• Uncaria sessilifructus

Cross-Links

• PubChem: 10749706
• NPASS: NPC102304
• LOTUS: LTS0266807
• wikiData: Q104976723