(3R,3aR,6aR,9aR,9bR)-Decahydro-3-hydroxy-3-(hydroxymethyl)-6,9-bis(methylene)azuleno[4,5-b]furan-2(3H)-one

Details

• Internal ID: fa4bad1f-b91b-4ac5-9edc-109145391c40
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3R,3aR,6aR,9aR,9bR)-3-hydroxy-3-(hydroxymethyl)-6,9-dimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): C=C1CCC2C(C3C1CCC3=C)OC(=O)C2(CO)O
• SMILES (Isomeric): C=C1CC[C@@H]2[C@@H]([C@@H]3[C@H]1CCC3=C)OC(=O)[C@@]2(CO)O
• InChI: InChI=1S/C15H20O4/c1-8-4-6-11-13(12-9(2)3-5-10(8)12)19-14(17)15(11,18)7-16/h10-13,16,18H,1-7H2/t10-,11+,12-,13-,15-/m0/s1
• InChI Key: RQNNFZZLPUJGMA-KBRXKUPHSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.32 g/mol
• Exact Mass: 264.13615911 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): 1.18
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• DTXSID001110038
• 96552-47-5
• (3R,3aR,6aR,9aR,9bR)-Decahydro-3-hydroxy-3-(hydroxymethyl)-6,9-bis(methylene)azuleno[4,5-b]furan-2(3H)-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9174	91.74%
Caco-2	-	0.7842	78.42%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6915	69.15%
OATP2B1 inhibitior	-	0.8537	85.37%
OATP1B1 inhibitior	+	0.9036	90.36%
OATP1B3 inhibitior	+	0.9616	96.16%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7292	72.92%
BSEP inhibitior	-	0.9479	94.79%
P-glycoprotein inhibitior	-	0.9388	93.88%
P-glycoprotein substrate	-	0.8978	89.78%
CYP3A4 substrate	+	0.5425	54.25%
CYP2C9 substrate	-	0.7875	78.75%
CYP2D6 substrate	-	0.8128	81.28%
CYP3A4 inhibition	-	0.9135	91.35%
CYP2C9 inhibition	-	0.8457	84.57%
CYP2C19 inhibition	-	0.7926	79.26%
CYP2D6 inhibition	-	0.9068	90.68%
CYP1A2 inhibition	-	0.8002	80.02%
CYP2C8 inhibition	-	0.8791	87.91%
CYP inhibitory promiscuity	-	0.9688	96.88%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6299	62.99%
Eye corrosion	-	0.9768	97.68%
Eye irritation	-	0.5245	52.45%
Skin irritation	-	0.6848	68.48%
Skin corrosion	-	0.9261	92.61%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8094	80.94%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.6554	65.54%
skin sensitisation	-	0.8556	85.56%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	+	0.5109	51.09%
Acute Oral Toxicity (c)	III	0.4307	43.07%
Estrogen receptor binding	-	0.6253	62.53%
Androgen receptor binding	+	0.5759	57.59%
Thyroid receptor binding	+	0.5508	55.08%
Glucocorticoid receptor binding	+	0.7099	70.99%
Aromatase binding	-	0.8057	80.57%
PPAR gamma	-	0.7398	73.98%
Honey bee toxicity	-	0.8910	89.10%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.8293	82.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.19%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.65%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.46%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.02%	100.00%
CHEMBL226	P30542	Adenosine A1 receptor	84.17%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.48%	95.56%
CHEMBL1978	P11511	Cytochrome P450 19A1	82.45%	91.76%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.62%	96.61%

Plants that contains it

• Helianthus petiolaris

Cross-Links

• PubChem: 10825507
• LOTUS: LTS0147239
• wikiData: Q105243441