(3aS,9S,9aR,9bS)-9,9a-dihydroxy-6,9-dimethyl-3-methylidene-3a,4,5,9b-tetrahydroazuleno[4,5-b]furan-2-one

Details

• Internal ID: 91971da8-ebf2-40fe-9d74-97fc0782283e
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3aS,9S,9aR,9bS)-9,9a-dihydroxy-6,9-dimethyl-3-methylidene-3a,4,5,9b-tetrahydroazuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=C2C=CC(C2(C3C(CC1)C(=C)C(=O)O3)O)(C)O
• SMILES (Isomeric): CC1=C2C=C[C@]([C@@]2([C@@H]3[C@@H](CC1)C(=C)C(=O)O3)O)(C)O
• InChI: InChI=1S/C15H18O4/c1-8-4-5-10-9(2)13(16)19-12(10)15(18)11(8)6-7-14(15,3)17/h6-7,10,12,17-18H,2,4-5H2,1,3H3/t10-,12-,14-,15+/m0/s1
• InChI Key: AVGKKZWHSWAMGC-HQRZJTNHSA-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: 0.20
• Atomic LogP (AlogP): 1.25
• 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	+	0.9523	95.23%
Caco-2	-	0.5222	52.22%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.6571	65.71%
Subcellular localzation	Mitochondria	0.5439	54.39%
OATP2B1 inhibitior	-	0.8560	85.60%
OATP1B1 inhibitior	+	0.9125	91.25%
OATP1B3 inhibitior	+	0.9505	95.05%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.9681	96.81%
P-glycoprotein inhibitior	-	0.9280	92.80%
P-glycoprotein substrate	-	0.8425	84.25%
CYP3A4 substrate	+	0.6214	62.14%
CYP2C9 substrate	-	0.8200	82.00%
CYP2D6 substrate	-	0.8568	85.68%
CYP3A4 inhibition	-	0.8305	83.05%
CYP2C9 inhibition	-	0.7403	74.03%
CYP2C19 inhibition	-	0.7272	72.72%
CYP2D6 inhibition	-	0.8714	87.14%
CYP1A2 inhibition	+	0.6847	68.47%
CYP2C8 inhibition	-	0.8153	81.53%
CYP inhibitory promiscuity	-	0.8810	88.10%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.4931	49.31%
Eye corrosion	-	0.9703	97.03%
Eye irritation	-	0.8934	89.34%
Skin irritation	-	0.5215	52.15%
Skin corrosion	-	0.8367	83.67%
Ames mutagenesis	-	0.7800	78.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5154	51.54%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.8250	82.50%
skin sensitisation	-	0.7371	73.71%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6000	60.00%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.4668	46.68%
Acute Oral Toxicity (c)	III	0.3680	36.80%
Estrogen receptor binding	-	0.4781	47.81%
Androgen receptor binding	+	0.5622	56.22%
Thyroid receptor binding	-	0.5302	53.02%
Glucocorticoid receptor binding	+	0.6025	60.25%
Aromatase binding	-	0.5072	50.72%
PPAR gamma	-	0.5741	57.41%
Honey bee toxicity	-	0.9183	91.83%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9720	97.20%

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	94.81%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.32%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.50%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.14%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.58%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.06%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.27%	97.25%
CHEMBL3192	Q9BY41	Histone deacetylase 8	83.94%	93.99%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.02%	94.45%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.77%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.52%	89.00%
CHEMBL4040	P28482	MAP kinase ERK2	81.09%	83.82%

Plants that contains it

• Ursinia nana

Cross-Links

• PubChem: 163039455
• LOTUS: LTS0222989
• wikiData: Q104919472