(5S,5aS,7R,8aR,9S)-1,5,9-trihydroxy-7-(hydroxymethyl)-5,7-dimethyl-4,5a,6,8,8a,9-hexahydro-1H-azuleno[5,6-c]furan-3-one

Details

• Internal ID: f9ee1fbd-f74c-4055-b4a8-b012217bc9b3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones
• IUPAC Name: (5S,5aS,7R,8aR,9S)-1,5,9-trihydroxy-7-(hydroxymethyl)-5,7-dimethyl-4,5a,6,8,8a,9-hexahydro-1H-azuleno[5,6-c]furan-3-one
• SMILES (Canonical): CC1(CC2C(C1)C(CC3=C(C2O)C(OC3=O)O)(C)O)CO
• SMILES (Isomeric): C[C@]1(C[C@@H]2[C@H](C1)[C@@](CC3=C([C@H]2O)C(OC3=O)O)(C)O)CO
• InChI: InChI=1S/C15H22O6/c1-14(6-16)3-7-9(5-14)15(2,20)4-8-10(11(7)17)13(19)21-12(8)18/h7,9,11,13,16-17,19-20H,3-6H2,1-2H3/t7-,9+,11+,13?,14-,15+/m1/s1
• InChI Key: ABPCODKOWLJTGL-PRQCOGANSA-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): 107.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -0.30
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9767	97.67%
Caco-2	-	0.6141	61.41%
Blood Brain Barrier	+	0.5058	50.58%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.5782	57.82%
OATP2B1 inhibitior	-	0.8547	85.47%
OATP1B1 inhibitior	+	0.9158	91.58%
OATP1B3 inhibitior	+	0.9584	95.84%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8317	83.17%
BSEP inhibitior	-	0.8484	84.84%
P-glycoprotein inhibitior	-	0.9110	91.10%
P-glycoprotein substrate	-	0.7846	78.46%
CYP3A4 substrate	+	0.5808	58.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8790	87.90%
CYP3A4 inhibition	-	0.8612	86.12%
CYP2C9 inhibition	-	0.8362	83.62%
CYP2C19 inhibition	-	0.8676	86.76%
CYP2D6 inhibition	-	0.9276	92.76%
CYP1A2 inhibition	-	0.7317	73.17%
CYP2C8 inhibition	-	0.8685	86.85%
CYP inhibitory promiscuity	-	0.9038	90.38%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6000	60.00%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.9649	96.49%
Skin irritation	-	0.6470	64.70%
Skin corrosion	-	0.9391	93.91%
Ames mutagenesis	+	0.5722	57.22%
Human Ether-a-go-go-Related Gene inhibition	-	0.5058	50.58%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.5448	54.48%
skin sensitisation	-	0.8540	85.40%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.6145	61.45%
Acute Oral Toxicity (c)	III	0.4876	48.76%
Estrogen receptor binding	+	0.6651	66.51%
Androgen receptor binding	-	0.5371	53.71%
Thyroid receptor binding	+	0.6180	61.80%
Glucocorticoid receptor binding	+	0.8399	83.99%
Aromatase binding	-	0.5958	59.58%
PPAR gamma	-	0.5841	58.41%
Honey bee toxicity	-	0.8992	89.92%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9336	93.36%

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	94.94%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.83%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.49%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.24%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.42%	95.56%
CHEMBL2581	P07339	Cathepsin D	87.98%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.84%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.40%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.22%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.86%	86.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 102275944
• LOTUS: LTS0097289
• wikiData: Q104399703