(3S,3aR,8S,9R,9aR,9bR)-8-hydroxy-6-(hydroxymethyl)-3,9-dimethyl-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

Details

• Internal ID: ef0f0e29-6f1b-45da-91e1-7861423f1ec9
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3S,3aR,8S,9R,9aR,9bR)-8-hydroxy-6-(hydroxymethyl)-3,9-dimethyl-3a,4,5,7,8,9,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1C(CC2=C(CCC3C(C(=O)OC3C12)C)CO)O
• SMILES (Isomeric): C[C@H]1[C@H](CC2=C(CC[C@@H]3[C@@H](C(=O)O[C@H]3[C@H]12)C)CO)O
• InChI: InChI=1S/C15H22O4/c1-7-10-4-3-9(6-16)11-5-12(17)8(2)13(11)14(10)19-15(7)18/h7-8,10,12-14,16-17H,3-6H2,1-2H3/t7-,8-,10+,12-,13+,14+/m0/s1
• InChI Key: UGBHLGXQNHUOHV-UMIWPCRESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.33 g/mol
• Exact Mass: 266.15180918 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): 1.26
• H-Bond Acceptor: 4
• 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	+	0.9855	98.55%
Caco-2	+	0.7235	72.35%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7512	75.12%
OATP2B1 inhibitior	-	0.8511	85.11%
OATP1B1 inhibitior	+	0.9084	90.84%
OATP1B3 inhibitior	+	0.9675	96.75%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6113	61.13%
BSEP inhibitior	-	0.9164	91.64%
P-glycoprotein inhibitior	-	0.9289	92.89%
P-glycoprotein substrate	-	0.6477	64.77%
CYP3A4 substrate	+	0.5364	53.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8410	84.10%
CYP3A4 inhibition	-	0.6820	68.20%
CYP2C9 inhibition	-	0.8910	89.10%
CYP2C19 inhibition	-	0.8662	86.62%
CYP2D6 inhibition	-	0.8814	88.14%
CYP1A2 inhibition	-	0.6059	60.59%
CYP2C8 inhibition	-	0.9360	93.60%
CYP inhibitory promiscuity	-	0.8902	89.02%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6698	66.98%
Eye corrosion	-	0.9842	98.42%
Eye irritation	-	0.8253	82.53%
Skin irritation	-	0.6515	65.15%
Skin corrosion	-	0.9420	94.20%
Ames mutagenesis	-	0.6337	63.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.6444	64.44%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.5052	50.52%
skin sensitisation	-	0.8539	85.39%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.5708	57.08%
Acute Oral Toxicity (c)	III	0.5051	50.51%
Estrogen receptor binding	-	0.5156	51.56%
Androgen receptor binding	+	0.5725	57.25%
Thyroid receptor binding	+	0.5377	53.77%
Glucocorticoid receptor binding	+	0.6114	61.14%
Aromatase binding	-	0.8130	81.30%
PPAR gamma	-	0.7617	76.17%
Honey bee toxicity	-	0.9078	90.78%
Biodegradation	-	0.5750	57.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9162	91.62%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.50%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.95%	91.11%
CHEMBL2581	P07339	Cathepsin D	91.13%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.47%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.65%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.49%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	85.96%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.82%	100.00%
CHEMBL2140	P48775	Tryptophan 2,3-dioxygenase	84.62%	98.46%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.80%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.12%	89.00%

Plants that contains it

• Echinops ritro

Cross-Links

• PubChem: 163093359
• LOTUS: LTS0211547
• wikiData: Q105272236