(3aR,5S,5aS,7S,8R,8aS,9aR)-7,8-dihydroxy-5,5a,8a-trimethyl-1-methylidene-3a,4,5,6,7,8,9,9a-octahydroazuleno[6,5-b]furan-2-one

Details

• Internal ID: f691ddd1-4f56-4591-a00d-5bccb7522ee6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: (3aR,5S,5aS,7S,8R,8aS,9aR)-7,8-dihydroxy-5,5a,8a-trimethyl-1-methylidene-3a,4,5,6,7,8,9,9a-octahydroazuleno[6,5-b]furan-2-one
• InChI: InChI=1S/C16H24O4/c1-8-5-12-10(9(2)14(19)20-12)6-16(4)13(18)11(17)7-15(8,16)3/h8,10-13,17-18H,2,5-7H2,1,3-4H3/t8-,10+,11-,12+,13-,15-,16+/m0/s1
• InChI Key: ACJYQFXQBFHCQK-XFSPDTKMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₂₄O₄
• Molecular Weight: 280.36 g/mol
• Exact Mass: 280.16745924 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.65
• H-Bond Acceptor: 4
• 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	+	0.9729	97.29%
Caco-2	+	0.5587	55.87%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5518	55.18%
OATP2B1 inhibitior	-	0.8527	85.27%
OATP1B1 inhibitior	+	0.8988	89.88%
OATP1B3 inhibitior	+	0.9330	93.30%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.9462	94.62%
P-glycoprotein inhibitior	-	0.9099	90.99%
P-glycoprotein substrate	-	0.8611	86.11%
CYP3A4 substrate	+	0.5531	55.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8422	84.22%
CYP3A4 inhibition	-	0.6150	61.50%
CYP2C9 inhibition	-	0.7906	79.06%
CYP2C19 inhibition	-	0.6915	69.15%
CYP2D6 inhibition	-	0.9408	94.08%
CYP1A2 inhibition	-	0.5894	58.94%
CYP2C8 inhibition	-	0.9019	90.19%
CYP inhibitory promiscuity	-	0.9605	96.05%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5756	57.56%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.8894	88.94%
Skin irritation	+	0.5095	50.95%
Skin corrosion	-	0.9124	91.24%
Ames mutagenesis	-	0.6424	64.24%
Human Ether-a-go-go-Related Gene inhibition	-	0.6210	62.10%
Micronuclear	-	0.6900	69.00%
Hepatotoxicity	+	0.7792	77.92%
skin sensitisation	-	0.7477	74.77%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.5431	54.31%
Acute Oral Toxicity (c)	III	0.4309	43.09%
Estrogen receptor binding	+	0.8491	84.91%
Androgen receptor binding	+	0.5445	54.45%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.6458	64.58%
Aromatase binding	+	0.5865	58.65%
PPAR gamma	-	0.5260	52.60%
Honey bee toxicity	-	0.8328	83.28%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9903	99.03%

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	98.26%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.47%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.03%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.36%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.98%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.89%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.98%	97.25%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.22%	86.33%
CHEMBL2996	Q05655	Protein kinase C delta	84.96%	97.79%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.85%	99.23%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.45%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.07%	100.00%

Plants that contains it

• Ambrosia tenuifolia

Cross-Links

• PubChem: 162917622
• LOTUS: LTS0233777
• wikiData: Q104909136