(3aR,9aS,9bR)-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione

Details

• Internal ID: e47d1ac4-764d-494b-8cce-cd920d31eca5
• Taxonomy: Organoheterocyclic compounds > Lactones > Gamma butyrolactones
• IUPAC Name: (3aR,9aS,9bR)-9-(hydroxymethyl)-6-methyl-3-methylidene-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
• SMILES (Canonical): CC1=C2C(C3C(CC1)C(=C)C(=O)O3)C(=CC2=O)CO
• SMILES (Isomeric): CC1=C2[C@@H]([C@H]3[C@H](CC1)C(=C)C(=O)O3)C(=CC2=O)CO
• InChI: InChI=1S/C15H16O4/c1-7-3-4-10-8(2)15(18)19-14(10)13-9(6-16)5-11(17)12(7)13/h5,10,13-14,16H,2-4,6H2,1H3/t10-,13+,14-/m1/s1
• InChI Key: NIYXMGSLECQTQT-DDTOSNHZSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₆O₄
• Molecular Weight: 260.28 g/mol
• Exact Mass: 260.10485899 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 1.31
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9887	98.87%
Caco-2	+	0.6048	60.48%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5866	58.66%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.8877	88.77%
OATP1B3 inhibitior	+	0.9435	94.35%
MATE1 inhibitior	-	0.8412	84.12%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.9340	93.40%
P-glycoprotein inhibitior	-	0.9233	92.33%
P-glycoprotein substrate	-	0.8615	86.15%
CYP3A4 substrate	+	0.5296	52.96%
CYP2C9 substrate	-	0.8092	80.92%
CYP2D6 substrate	-	0.9038	90.38%
CYP3A4 inhibition	-	0.8733	87.33%
CYP2C9 inhibition	-	0.7997	79.97%
CYP2C19 inhibition	-	0.8404	84.04%
CYP2D6 inhibition	-	0.8685	86.85%
CYP1A2 inhibition	+	0.6109	61.09%
CYP2C8 inhibition	-	0.8018	80.18%
CYP inhibitory promiscuity	-	0.9171	91.71%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.6091	60.91%
Eye corrosion	-	0.9405	94.05%
Eye irritation	-	0.6612	66.12%
Skin irritation	-	0.5460	54.60%
Skin corrosion	-	0.8640	86.40%
Ames mutagenesis	-	0.6970	69.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.7383	73.83%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	+	0.7125	71.25%
skin sensitisation	-	0.7358	73.58%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5209	52.09%
Acute Oral Toxicity (c)	III	0.5916	59.16%
Estrogen receptor binding	-	0.6996	69.96%
Androgen receptor binding	+	0.6917	69.17%
Thyroid receptor binding	-	0.5785	57.85%
Glucocorticoid receptor binding	+	0.6116	61.16%
Aromatase binding	-	0.8188	81.88%
PPAR gamma	-	0.6997	69.97%
Honey bee toxicity	-	0.9232	92.32%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9606	96.06%

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	91.37%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	90.32%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.25%	95.56%
CHEMBL2581	P07339	Cathepsin D	89.23%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.83%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.84%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.40%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.01%	99.23%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.69%	94.45%

Plants that contains it

• Cichorium endivia

Cross-Links

• PubChem: 162948961
• LOTUS: LTS0147068
• wikiData: Q105180039