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

Details

• Internal ID: 3cafc68a-9363-4906-827c-a92c7dd7c977
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3aS,5R,6S,6aR,8S,9bS)-5,6,8-trihydroxy-6,9-dimethyl-3-methylidene-4,5,6a,7,8,9b-hexahydro-3aH-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1=C2C(CC1O)C(C(CC3C2OC(=O)C3=C)O)(C)O
• SMILES (Isomeric): CC1=C2[C@@H](C[C@@H]1O)[C@]([C@@H](C[C@@H]3[C@@H]2OC(=O)C3=C)O)(C)O
• InChI: InChI=1S/C15H20O5/c1-6-8-4-11(17)15(3,19)9-5-10(16)7(2)12(9)13(8)20-14(6)18/h8-11,13,16-17,19H,1,4-5H2,2-3H3/t8-,9+,10-,11+,13-,15-/m0/s1
• InChI Key: DPYNIKWDGAULLI-BAFIMQKQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₀O₅
• Molecular Weight: 280.32 g/mol
• Exact Mass: 280.13107373 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: -0.90
• Atomic LogP (AlogP): 0.30
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9726	97.26%
Caco-2	-	0.5805	58.05%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6345	63.45%
OATP2B1 inhibitior	-	0.8537	85.37%
OATP1B1 inhibitior	+	0.8705	87.05%
OATP1B3 inhibitior	+	0.9374	93.74%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.9714	97.14%
P-glycoprotein inhibitior	-	0.9244	92.44%
P-glycoprotein substrate	-	0.7993	79.93%
CYP3A4 substrate	+	0.5756	57.56%
CYP2C9 substrate	-	0.8087	80.87%
CYP2D6 substrate	-	0.8486	84.86%
CYP3A4 inhibition	-	0.8199	81.99%
CYP2C9 inhibition	-	0.8284	82.84%
CYP2C19 inhibition	-	0.7637	76.37%
CYP2D6 inhibition	-	0.9122	91.22%
CYP1A2 inhibition	-	0.6564	65.64%
CYP2C8 inhibition	-	0.8514	85.14%
CYP inhibitory promiscuity	-	0.9543	95.43%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5534	55.34%
Eye corrosion	-	0.9809	98.09%
Eye irritation	-	0.7904	79.04%
Skin irritation	-	0.5565	55.65%
Skin corrosion	-	0.8755	87.55%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5256	52.56%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	+	0.7074	70.74%
skin sensitisation	-	0.7342	73.42%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.7030	70.30%
Acute Oral Toxicity (c)	III	0.4107	41.07%
Estrogen receptor binding	+	0.6483	64.83%
Androgen receptor binding	-	0.5503	55.03%
Thyroid receptor binding	+	0.5623	56.23%
Glucocorticoid receptor binding	+	0.7932	79.32%
Aromatase binding	-	0.5898	58.98%
PPAR gamma	-	0.6317	63.17%
Honey bee toxicity	-	0.8635	86.35%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9594	95.94%

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	94.84%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.77%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.35%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.72%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.54%	97.25%
CHEMBL2996	Q05655	Protein kinase C delta	87.31%	97.79%
CHEMBL2581	P07339	Cathepsin D	86.98%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.55%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.17%	96.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.07%	96.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.64%	95.50%

Plants that contains it

• Ajania achilleoides

Cross-Links

• PubChem: 162930124
• LOTUS: LTS0131779
• wikiData: Q104986797