(3aS,6aS,9aS,9bS)-6a-hydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-4,7,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2-one

Details

• Internal ID: 7ff80d38-2e08-4b0d-b6f6-049ecdb5db33
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6aS,9aS,9bS)-6a-hydroxy-6-(hydroxymethyl)-9-methyl-3-methylidene-4,7,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=CCC2(C1C3C(CC=C2CO)C(=C)C(=O)O3)O
• SMILES (Isomeric): CC1=CC[C@@]2([C@@H]1[C@@H]3[C@@H](CC=C2CO)C(=C)C(=O)O3)O
• InChI: InChI=1S/C15H18O4/c1-8-5-6-15(18)10(7-16)3-4-11-9(2)14(17)19-13(11)12(8)15/h3,5,11-13,16,18H,2,4,6-7H2,1H3/t11-,12-,13-,15+/m0/s1
• InChI Key: SBDNSRXBOGYUOH-PWNZVWSESA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30 g/mol
• Exact Mass: 262.12050905 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): 1.10
• 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	+	0.9576	95.76%
Caco-2	-	0.6566	65.66%
Blood Brain Barrier	+	0.5527	55.27%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.5186	51.86%
OATP2B1 inhibitior	-	0.8559	85.59%
OATP1B1 inhibitior	+	0.8964	89.64%
OATP1B3 inhibitior	+	0.9619	96.19%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9479	94.79%
P-glycoprotein inhibitior	-	0.9328	93.28%
P-glycoprotein substrate	-	0.8393	83.93%
CYP3A4 substrate	+	0.5852	58.52%
CYP2C9 substrate	-	0.7929	79.29%
CYP2D6 substrate	-	0.8582	85.82%
CYP3A4 inhibition	-	0.9343	93.43%
CYP2C9 inhibition	-	0.8717	87.17%
CYP2C19 inhibition	-	0.8611	86.11%
CYP2D6 inhibition	-	0.9403	94.03%
CYP1A2 inhibition	-	0.7946	79.46%
CYP2C8 inhibition	-	0.7954	79.54%
CYP inhibitory promiscuity	-	0.9120	91.20%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6468	64.68%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.8815	88.15%
Skin irritation	-	0.6374	63.74%
Skin corrosion	-	0.9252	92.52%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5627	56.27%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	+	0.6303	63.03%
skin sensitisation	-	0.8341	83.41%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.5857	58.57%
Acute Oral Toxicity (c)	III	0.4608	46.08%
Estrogen receptor binding	+	0.5457	54.57%
Androgen receptor binding	+	0.5978	59.78%
Thyroid receptor binding	-	0.5576	55.76%
Glucocorticoid receptor binding	+	0.6254	62.54%
Aromatase binding	-	0.6276	62.76%
PPAR gamma	-	0.6004	60.04%
Honey bee toxicity	-	0.8455	84.55%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9460	94.60%

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	94.96%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.35%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.98%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.30%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.51%	94.45%
CHEMBL4530	P00488	Coagulation factor XIII	84.46%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.24%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.45%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.25%	97.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.62%	91.24%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.80%	100.00%
CHEMBL2581	P07339	Cathepsin D	80.32%	98.95%

Plants that contains it

• Artemisia xerophytica

Cross-Links

• PubChem: 163002898
• LOTUS: LTS0017926
• wikiData: Q105249339