(3aR,6S,7R,7aS)-6,7-dihydroxy-6-methyl-3-methylenehexahydrobenzofuran-2(3H)-one

Details

• Internal ID: fa4dfe40-8d71-48e3-ab85-6cb7ca1bd398
• Taxonomy: Organoheterocyclic compounds > Benzofurans
• IUPAC Name: (3aR,6S,7R,7aS)-6,7-dihydroxy-6-methyl-3-methylidene-4,5,7,7a-tetrahydro-3aH-1-benzofuran-2-one
• SMILES (Canonical): CC1(CCC2C(C1O)OC(=O)C2=C)O
• SMILES (Isomeric): C[C@@]1(CC[C@H]2[C@@H]([C@H]1O)OC(=O)C2=C)O
• InChI: InChI=1S/C10H14O4/c1-5-6-3-4-10(2,13)8(11)7(6)14-9(5)12/h6-8,11,13H,1,3-4H2,2H3/t6-,7+,8-,10+/m1/s1
• InChI Key: ZVMVPIWZXUSVAO-JIOCBJNQSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.22 g/mol
• Exact Mass: 198.08920892 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): -0.01
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

• RefChem:69148
• (3aR,6S,7R,7aS)-6,7-dihydroxy-6-methyl-3-methylidene-4,5,7,7a-tetrahydro-3aH-1-benzofuran-2-one
• CHEBI:198386
• (3aR,6S,7R,7aS)-6,7-dihydroxy-6-methyl-3-methylidene-4,5,7,7a-tetrahydro-3aH-1-benzouran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9723	97.23%
Caco-2	-	0.8110	81.10%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6454	64.54%
OATP2B1 inhibitior	-	0.8512	85.12%
OATP1B1 inhibitior	+	0.8917	89.17%
OATP1B3 inhibitior	+	0.9402	94.02%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8071	80.71%
BSEP inhibitior	-	0.9901	99.01%
P-glycoprotein inhibitior	-	0.9614	96.14%
P-glycoprotein substrate	-	0.9370	93.70%
CYP3A4 substrate	+	0.5504	55.04%
CYP2C9 substrate	-	0.8087	80.87%
CYP2D6 substrate	-	0.8486	84.86%
CYP3A4 inhibition	-	0.8635	86.35%
CYP2C9 inhibition	-	0.8739	87.39%
CYP2C19 inhibition	-	0.7857	78.57%
CYP2D6 inhibition	-	0.9115	91.15%
CYP1A2 inhibition	-	0.6656	66.56%
CYP2C8 inhibition	-	0.8886	88.86%
CYP inhibitory promiscuity	-	0.9473	94.73%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4956	49.56%
Eye corrosion	-	0.9794	97.94%
Eye irritation	-	0.8734	87.34%
Skin irritation	+	0.5309	53.09%
Skin corrosion	-	0.8076	80.76%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7262	72.62%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	+	0.8574	85.74%
skin sensitisation	-	0.7434	74.34%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6984	69.84%
Acute Oral Toxicity (c)	III	0.3346	33.46%
Estrogen receptor binding	+	0.5839	58.39%
Androgen receptor binding	-	0.5297	52.97%
Thyroid receptor binding	-	0.7129	71.29%
Glucocorticoid receptor binding	-	0.5640	56.40%
Aromatase binding	-	0.7911	79.11%
PPAR gamma	-	0.8003	80.03%
Honey bee toxicity	-	0.8650	86.50%
Biodegradation	+	0.5500	55.00%
Crustacea aquatic toxicity	+	0.5400	54.00%
Fish aquatic toxicity	+	0.9370	93.70%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.41%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.96%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.14%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.47%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	85.43%	97.79%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.23%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.01%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.43%	94.45%
CHEMBL2581	P07339	Cathepsin D	80.36%	98.95%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 71655106
• LOTUS: LTS0252846
• wikiData: Q75059608