(3aS,6S,6aS,8R,9S,9aS,9bS)-8,9-dihydroxy-6,9a-dimethyl-3-methylidene-4,5,6,6a,7,8,9,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 5f17c16c-a520-418c-965f-b8f39be94701
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: (3aS,6S,6aS,8R,9S,9aS,9bS)-8,9-dihydroxy-6,9a-dimethyl-3-methylidene-4,5,6,6a,7,8,9,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1CCC2C(C3(C1CC(C3O)O)C)OC(=O)C2=C
• SMILES (Isomeric): C[C@H]1CC[C@@H]2[C@@H]([C@]3([C@H]1C[C@H]([C@H]3O)O)C)OC(=O)C2=C
• InChI: InChI=1S/C15H22O4/c1-7-4-5-9-8(2)14(18)19-13(9)15(3)10(7)6-11(16)12(15)17/h7,9-13,16-17H,2,4-6H2,1,3H3/t7-,9-,10-,11+,12+,13-,15-/m0/s1
• InChI Key: UOGCXTUFYJBFHD-QWFDUNJNSA-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: 1.90
• Atomic LogP (AlogP): 1.26
• 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	+	0.9620	96.20%
Caco-2	+	0.5055	50.55%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6199	61.99%
OATP2B1 inhibitior	-	0.8513	85.13%
OATP1B1 inhibitior	+	0.8955	89.55%
OATP1B3 inhibitior	+	0.9313	93.13%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6821	68.21%
BSEP inhibitior	-	0.9577	95.77%
P-glycoprotein inhibitior	-	0.8946	89.46%
P-glycoprotein substrate	-	0.7828	78.28%
CYP3A4 substrate	+	0.6203	62.03%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8422	84.22%
CYP3A4 inhibition	-	0.7361	73.61%
CYP2C9 inhibition	-	0.7455	74.55%
CYP2C19 inhibition	-	0.6418	64.18%
CYP2D6 inhibition	-	0.9383	93.83%
CYP1A2 inhibition	+	0.6396	63.96%
CYP2C8 inhibition	-	0.7951	79.51%
CYP inhibitory promiscuity	-	0.9726	97.26%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5539	55.39%
Eye corrosion	-	0.9864	98.64%
Eye irritation	-	0.9037	90.37%
Skin irritation	+	0.5481	54.81%
Skin corrosion	-	0.8967	89.67%
Ames mutagenesis	-	0.7064	70.64%
Human Ether-a-go-go-Related Gene inhibition	-	0.8514	85.14%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.7712	77.12%
skin sensitisation	-	0.7995	79.95%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	IV	0.2867	28.67%
Estrogen receptor binding	+	0.6669	66.69%
Androgen receptor binding	+	0.5337	53.37%
Thyroid receptor binding	-	0.5752	57.52%
Glucocorticoid receptor binding	+	0.7444	74.44%
Aromatase binding	-	0.5647	56.47%
PPAR gamma	-	0.5930	59.30%
Honey bee toxicity	-	0.8151	81.51%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9841	98.41%

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	99.34%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.59%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.97%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.18%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.12%	99.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.91%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.96%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.62%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.45%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.93%	97.14%

Plants that contains it

• Ambrosia psilostachya

Cross-Links

• PubChem: 162982142
• LOTUS: LTS0171837
• wikiData: Q105276334