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

Details

• Internal ID: 71fefdbc-3f62-447d-b9e3-daa706cfc455
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3S,3aR,4S,6R,6aS,8S,9aS,9bR)-4,8-dihydroxy-3,6-dimethyl-9-methylidene-3,3a,4,5,6,6a,7,8,9a,9b-decahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1CC(C2C(C(=O)OC2C3C1CC(C3=C)O)C)O
• SMILES (Isomeric): C[C@@H]1C[C@@H]([C@H]2[C@@H](C(=O)O[C@@H]2[C@H]3[C@H]1C[C@@H](C3=C)O)C)O
• InChI: InChI=1S/C15H22O4/c1-6-4-11(17)13-8(3)15(18)19-14(13)12-7(2)10(16)5-9(6)12/h6,8-14,16-17H,2,4-5H2,1,3H3/t6-,8+,9+,10+,11+,12-,13-,14-/m1/s1
• InChI Key: IBIJTDJAWRYXRF-FURRRUDJSA-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: 1.10
• Atomic LogP (AlogP): 1.12
• 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	+	0.9892	98.92%
Caco-2	+	0.5818	58.18%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.4276	42.76%
OATP2B1 inhibitior	-	0.8550	85.50%
OATP1B1 inhibitior	+	0.9190	91.90%
OATP1B3 inhibitior	+	0.9445	94.45%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9660	96.60%
P-glycoprotein inhibitior	-	0.9152	91.52%
P-glycoprotein substrate	-	0.7928	79.28%
CYP3A4 substrate	+	0.5608	56.08%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8313	83.13%
CYP3A4 inhibition	-	0.6928	69.28%
CYP2C9 inhibition	-	0.9083	90.83%
CYP2C19 inhibition	-	0.8505	85.05%
CYP2D6 inhibition	-	0.9397	93.97%
CYP1A2 inhibition	-	0.5820	58.20%
CYP2C8 inhibition	-	0.9395	93.95%
CYP inhibitory promiscuity	-	0.9240	92.40%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5272	52.72%
Eye corrosion	-	0.9650	96.50%
Eye irritation	-	0.9041	90.41%
Skin irritation	-	0.5437	54.37%
Skin corrosion	-	0.8941	89.41%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8300	83.00%
Micronuclear	-	0.6700	67.00%
Hepatotoxicity	+	0.7712	77.12%
skin sensitisation	-	0.7010	70.10%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.6605	66.05%
Acute Oral Toxicity (c)	II	0.3775	37.75%
Estrogen receptor binding	-	0.6291	62.91%
Androgen receptor binding	+	0.5195	51.95%
Thyroid receptor binding	-	0.5275	52.75%
Glucocorticoid receptor binding	-	0.5876	58.76%
Aromatase binding	-	0.7318	73.18%
PPAR gamma	-	0.8274	82.74%
Honey bee toxicity	-	0.7658	76.58%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9795	97.95%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	92.83%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.44%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.04%	85.14%
CHEMBL1871	P10275	Androgen Receptor	85.25%	96.43%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.55%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.87%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.06%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.84%	99.23%
CHEMBL4803	P29474	Nitric-oxide synthase, endothelial	81.82%	86.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.40%	93.04%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.00%	97.09%

Plants that contains it

• Artemisia absinthium

Cross-Links

• PubChem: 163194835
• LOTUS: LTS0113881
• wikiData: Q105036514