(1aR,3aS,5E,7R,7aS)-3a,7-dihydroxy-2,2-dimethyl-5-(2-oxopropylidene)-1,1a,6,7-tetrahydrocyclopropa[c][1]benzofuran-4-one

Details

• Internal ID: a1700ac9-b637-4268-b12e-972a3a2a1b74
• Taxonomy: Organoheterocyclic compounds > Oxanes
• IUPAC Name: (1aR,3aS,5E,7R,7aS)-3a,7-dihydroxy-2,2-dimethyl-5-(2-oxopropylidene)-1,1a,6,7-tetrahydrocyclopropa[c][1]benzofuran-4-one
• SMILES (Canonical): CC(=O)C=C1CC(C23CC2C(OC3(C1=O)O)(C)C)O
• SMILES (Isomeric): CC(=O)/C=C/1\C[C@H]([C@]23C[C@H]2C(O[C@@]3(C1=O)O)(C)C)O
• InChI: InChI=1S/C14H18O5/c1-7(15)4-8-5-10(16)13-6-9(13)12(2,3)19-14(13,18)11(8)17/h4,9-10,16,18H,5-6H2,1-3H3/b8-4+/t9-,10+,13-,14+/m0/s1
• InChI Key: LKNPZQZUTUAUNZ-HDYZZQQVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.29 g/mol
• Exact Mass: 266.11542367 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): 0.34
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9634	96.34%
Caco-2	-	0.6198	61.98%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6847	68.47%
OATP2B1 inhibitior	-	0.8528	85.28%
OATP1B1 inhibitior	+	0.9236	92.36%
OATP1B3 inhibitior	+	0.9352	93.52%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9521	95.21%
P-glycoprotein inhibitior	-	0.9193	91.93%
P-glycoprotein substrate	-	0.8269	82.69%
CYP3A4 substrate	+	0.5720	57.20%
CYP2C9 substrate	-	0.7872	78.72%
CYP2D6 substrate	-	0.8684	86.84%
CYP3A4 inhibition	-	0.7412	74.12%
CYP2C9 inhibition	-	0.8728	87.28%
CYP2C19 inhibition	-	0.8819	88.19%
CYP2D6 inhibition	-	0.9338	93.38%
CYP1A2 inhibition	-	0.8789	87.89%
CYP2C8 inhibition	-	0.9221	92.21%
CYP inhibitory promiscuity	-	0.9064	90.64%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5156	51.56%
Eye corrosion	-	0.9884	98.84%
Eye irritation	-	0.7348	73.48%
Skin irritation	-	0.5355	53.55%
Skin corrosion	-	0.9106	91.06%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5668	56.68%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	-	0.6426	64.26%
skin sensitisation	-	0.7632	76.32%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.8750	87.50%
Nephrotoxicity	+	0.6393	63.93%
Acute Oral Toxicity (c)	I	0.5832	58.32%
Estrogen receptor binding	+	0.8345	83.45%
Androgen receptor binding	+	0.5986	59.86%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.5486	54.86%
Aromatase binding	-	0.4901	49.01%
PPAR gamma	+	0.6548	65.48%
Honey bee toxicity	-	0.8578	85.78%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9793	97.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.67%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.01%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.56%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.25%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.00%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.83%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	84.11%	94.75%
CHEMBL5103	Q969S8	Histone deacetylase 10	83.08%	90.08%
CHEMBL340	P08684	Cytochrome P450 3A4	83.05%	91.19%
CHEMBL2581	P07339	Cathepsin D	82.97%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.24%	99.23%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162843319
• LOTUS: LTS0162403
• wikiData: Q105153168