(5S,5aR,6R,7S,8aR)-6-hydroxy-7-(hydroxymethyl)-5,7-dimethyl-1,4,5,5a,6,8,8a,9-octahydroazuleno[5,6-c]furan-3-one

Details

• Internal ID: 51b4a057-59d9-4bc1-84f2-e9735bb3d6ec
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (5S,5aR,6R,7S,8aR)-6-hydroxy-7-(hydroxymethyl)-5,7-dimethyl-1,4,5,5a,6,8,8a,9-octahydroazuleno[5,6-c]furan-3-one
• SMILES (Canonical): CC1CC2=C(CC3C1C(C(C3)(C)CO)O)COC2=O
• SMILES (Isomeric): C[C@H]1CC2=C(C[C@H]3[C@@H]1[C@H]([C@](C3)(C)CO)O)COC2=O
• InChI: InChI=1S/C15H22O4/c1-8-3-11-10(6-19-14(11)18)4-9-5-15(2,7-16)13(17)12(8)9/h8-9,12-13,16-17H,3-7H2,1-2H3/t8-,9+,12+,13+,15-/m0/s1
• InChI Key: XNCROXXXRUTAOE-KLDWPMRUSA-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: 1.40
• Atomic LogP (AlogP): 1.27
• 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	+	0.9270	92.70%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	+	0.5808	58.08%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6268	62.68%
OATP2B1 inhibitior	-	0.8523	85.23%
OATP1B1 inhibitior	+	0.8990	89.90%
OATP1B3 inhibitior	+	0.9484	94.84%
MATE1 inhibitior	-	0.8212	82.12%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6327	63.27%
P-glycoprotein inhibitior	-	0.9282	92.82%
P-glycoprotein substrate	-	0.8301	83.01%
CYP3A4 substrate	+	0.5442	54.42%
CYP2C9 substrate	-	0.8086	80.86%
CYP2D6 substrate	-	0.8794	87.94%
CYP3A4 inhibition	-	0.8999	89.99%
CYP2C9 inhibition	-	0.7940	79.40%
CYP2C19 inhibition	-	0.8043	80.43%
CYP2D6 inhibition	-	0.9212	92.12%
CYP1A2 inhibition	-	0.6984	69.84%
CYP2C8 inhibition	-	0.9389	93.89%
CYP inhibitory promiscuity	-	0.7828	78.28%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5413	54.13%
Eye corrosion	-	0.9814	98.14%
Eye irritation	-	0.8600	86.00%
Skin irritation	-	0.6926	69.26%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	+	0.6363	63.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.5627	56.27%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.6627	66.27%
skin sensitisation	-	0.8392	83.92%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.6635	66.35%
Acute Oral Toxicity (c)	III	0.4668	46.68%
Estrogen receptor binding	-	0.5395	53.95%
Androgen receptor binding	-	0.4865	48.65%
Thyroid receptor binding	+	0.6088	60.88%
Glucocorticoid receptor binding	+	0.7265	72.65%
Aromatase binding	-	0.6830	68.30%
PPAR gamma	-	0.5777	57.77%
Honey bee toxicity	-	0.8461	84.61%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9671	96.71%

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	94.64%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.76%	96.09%
CHEMBL2581	P07339	Cathepsin D	91.49%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.63%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.02%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.52%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.46%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.31%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.74%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	80.25%	90.17%
CHEMBL299	P17252	Protein kinase C alpha	80.21%	98.03%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 163000598
• LOTUS: LTS0093850
• wikiData: Q105331562