(1S,3S,5R,8S)-3,8-dihydroxy-8-[(E,3R)-3-hydroxybut-1-enyl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-7-one

Details

• Internal ID: af4b6241-8016-4ef8-9636-27a8521889c8
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (1S,3S,5R,8S)-3,8-dihydroxy-8-[(E,3R)-3-hydroxybut-1-enyl]-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-7-one
• SMILES (Canonical): CC(C=CC1(C2(CC(CC1(OC2=O)C)O)C)O)O
• SMILES (Isomeric): C[C@H](/C=C/[C@@]1([C@@]2(C[C@@H](C[C@]1(OC2=O)C)O)C)O)O
• InChI: InChI=1S/C13H20O5/c1-8(14)4-5-13(17)11(2)6-9(15)7-12(13,3)18-10(11)16/h4-5,8-9,14-15,17H,6-7H2,1-3H3/b5-4+/t8-,9+,11-,12-,13+/m1/s1
• InChI Key: AQSPKQLQWIQRJJ-WKINKLLYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₀O₅
• Molecular Weight: 256.29 g/mol
• Exact Mass: 256.13107373 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: -0.50
• Atomic LogP (AlogP): 0.13
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9643	96.43%
Caco-2	+	0.6730	67.30%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.5716	57.16%
OATP2B1 inhibitior	-	0.8518	85.18%
OATP1B1 inhibitior	+	0.9330	93.30%
OATP1B3 inhibitior	+	0.9166	91.66%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7785	77.85%
P-glycoprotein inhibitior	-	0.9686	96.86%
P-glycoprotein substrate	-	0.8724	87.24%
CYP3A4 substrate	+	0.5596	55.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8411	84.11%
CYP3A4 inhibition	-	0.8423	84.23%
CYP2C9 inhibition	-	0.9496	94.96%
CYP2C19 inhibition	-	0.9119	91.19%
CYP2D6 inhibition	-	0.9711	97.11%
CYP1A2 inhibition	-	0.8707	87.07%
CYP2C8 inhibition	-	0.9417	94.17%
CYP inhibitory promiscuity	-	0.9748	97.48%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5145	51.45%
Eye corrosion	-	0.9817	98.17%
Eye irritation	-	0.7820	78.20%
Skin irritation	-	0.5704	57.04%
Skin corrosion	-	0.8887	88.87%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8639	86.39%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.5658	56.58%
skin sensitisation	-	0.7286	72.86%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.5333	53.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.6166	61.66%
Acute Oral Toxicity (c)	III	0.4038	40.38%
Estrogen receptor binding	-	0.7936	79.36%
Androgen receptor binding	+	0.6327	63.27%
Thyroid receptor binding	+	0.6347	63.47%
Glucocorticoid receptor binding	-	0.5902	59.02%
Aromatase binding	-	0.6278	62.78%
PPAR gamma	-	0.6338	63.38%
Honey bee toxicity	-	0.8413	84.13%
Biodegradation	-	0.5000	50.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.8803	88.03%

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	95.27%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.10%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.54%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.13%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.80%	97.25%
CHEMBL2581	P07339	Cathepsin D	86.36%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.93%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.63%	89.00%
CHEMBL221	P23219	Cyclooxygenase-1	84.05%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.79%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.16%	96.77%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.69%	99.23%
CHEMBL3401	O75469	Pregnane X receptor	81.63%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.87%	100.00%

Plants that contains it

• Silene baccifera

Cross-Links

• PubChem: 10729754
• LOTUS: LTS0157295
• wikiData: Q104917037