(3S,3aS,6R,7S,8R,8aR)-6,8-dihydroxy-3,6,8-trimethylspiro[3a,4,5,8a-tetrahydro-3H-cyclohepta[b]furan-7,5'-oxolane]-2,2'-dione

Details

• Internal ID: d8457eba-0210-49ee-b39d-2feae025e525
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3S,3aS,6R,7S,8R,8aR)-6,8-dihydroxy-3,6,8-trimethylspiro[3a,4,5,8a-tetrahydro-3H-cyclohepta[b]furan-7,5'-oxolane]-2,2'-dione
• SMILES (Canonical): CC1C2CCC(C3(CCC(=O)O3)C(C2OC1=O)(C)O)(C)O
• SMILES (Isomeric): C[C@H]1[C@@H]2CC[C@@]([C@@]3(CCC(=O)O3)[C@]([C@@H]2OC1=O)(C)O)(C)O
• InChI: InChI=1S/C15H22O6/c1-8-9-4-6-13(2,18)15(7-5-10(16)21-15)14(3,19)11(9)20-12(8)17/h8-9,11,18-19H,4-7H2,1-3H3/t8-,9-,11+,13+,14+,15-/m0/s1
• InChI Key: OOVPUQLRCZYQEA-NYAQSBGISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₆
• Molecular Weight: 298.33 g/mol
• Exact Mass: 298.14163842 g/mol
• Topological Polar Surface Area (TPSA): 93.10 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 0.54
• H-Bond Acceptor: 6
• 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	+	0.8588	85.88%
Caco-2	-	0.6344	63.44%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	+	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5538	55.38%
OATP2B1 inhibitior	-	0.8554	85.54%
OATP1B1 inhibitior	+	0.9021	90.21%
OATP1B3 inhibitior	+	0.9184	91.84%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8071	80.71%
BSEP inhibitior	-	0.9180	91.80%
P-glycoprotein inhibitior	-	0.8666	86.66%
P-glycoprotein substrate	-	0.8033	80.33%
CYP3A4 substrate	+	0.6170	61.70%
CYP2C9 substrate	-	0.8009	80.09%
CYP2D6 substrate	-	0.8363	83.63%
CYP3A4 inhibition	-	0.8184	81.84%
CYP2C9 inhibition	-	0.8478	84.78%
CYP2C19 inhibition	-	0.8397	83.97%
CYP2D6 inhibition	-	0.9655	96.55%
CYP1A2 inhibition	-	0.6474	64.74%
CYP2C8 inhibition	-	0.8477	84.77%
CYP inhibitory promiscuity	-	0.9894	98.94%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5786	57.86%
Eye corrosion	-	0.9869	98.69%
Eye irritation	-	0.9525	95.25%
Skin irritation	-	0.5257	52.57%
Skin corrosion	-	0.8469	84.69%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8090	80.90%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.7250	72.50%
skin sensitisation	-	0.8847	88.47%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.6553	65.53%
Acute Oral Toxicity (c)	III	0.3292	32.92%
Estrogen receptor binding	+	0.8393	83.93%
Androgen receptor binding	+	0.6368	63.68%
Thyroid receptor binding	-	0.5304	53.04%
Glucocorticoid receptor binding	-	0.4638	46.38%
Aromatase binding	+	0.5189	51.89%
PPAR gamma	+	0.5370	53.70%
Honey bee toxicity	-	0.8603	86.03%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5800	58.00%
Fish aquatic toxicity	+	0.8840	88.40%

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	95.78%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.30%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.33%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.13%	100.00%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	84.26%	96.38%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.11%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.04%	99.23%
CHEMBL1871	P10275	Androgen Receptor	81.73%	96.43%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.57%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.03%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.92%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.89%	97.14%

Plants that contains it

• Ambrosia arborescens

Cross-Links

• PubChem: 162919704
• LOTUS: LTS0123955
• wikiData: Q105195659