(3aS,5R,5aR,7S,8aS,9aR)-5-(chloromethyl)-5,7,8a-trihydroxy-1-methyl-8-methylidene-1,3a,4,5a,6,7,9,9a-octahydroazuleno[6,5-b]furan-2-one

Details

• Internal ID: 662ae0df-5fc6-4f62-97a8-f0f968ec95d7
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,5R,5aR,7S,8aS,9aR)-5-(chloromethyl)-5,7,8a-trihydroxy-1-methyl-8-methylidene-1,3a,4,5a,6,7,9,9a-octahydroazuleno[6,5-b]furan-2-one
• InChI: InChI=1S/C15H21ClO5/c1-7-9-4-15(20)8(2)10(17)3-12(15)14(19,6-16)5-11(9)21-13(7)18/h7,9-12,17,19-20H,2-6H2,1H3/t7?,9-,10+,11+,12+,14+,15-/m1/s1
• InChI Key: NAVPGMZDCRNXQS-GMUQWCIUSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₁ClO₅
• Molecular Weight: 316.77 g/mol
• Exact Mass: 316.1077515 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.60
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9759	97.59%
Caco-2	-	0.7496	74.96%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5421	54.21%
OATP2B1 inhibitior	-	0.8537	85.37%
OATP1B1 inhibitior	+	0.9126	91.26%
OATP1B3 inhibitior	+	0.9493	94.93%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.8584	85.84%
P-glycoprotein inhibitior	-	0.9269	92.69%
P-glycoprotein substrate	-	0.6629	66.29%
CYP3A4 substrate	+	0.6376	63.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8526	85.26%
CYP3A4 inhibition	-	0.8667	86.67%
CYP2C9 inhibition	-	0.8465	84.65%
CYP2C19 inhibition	-	0.7819	78.19%
CYP2D6 inhibition	-	0.9253	92.53%
CYP1A2 inhibition	-	0.7393	73.93%
CYP2C8 inhibition	-	0.8935	89.35%
CYP inhibitory promiscuity	-	0.9108	91.08%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8544	85.44%
Carcinogenicity (trinary)	Non-required	0.5077	50.77%
Eye corrosion	-	0.9799	97.99%
Eye irritation	-	0.9758	97.58%
Skin irritation	-	0.6136	61.36%
Skin corrosion	-	0.8913	89.13%
Ames mutagenesis	+	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6685	66.85%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	+	0.6866	68.66%
skin sensitisation	-	0.7761	77.61%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	+	0.8124	81.24%
Acute Oral Toxicity (c)	III	0.4262	42.62%
Estrogen receptor binding	+	0.7848	78.48%
Androgen receptor binding	-	0.5088	50.88%
Thyroid receptor binding	+	0.6109	61.09%
Glucocorticoid receptor binding	+	0.7983	79.83%
Aromatase binding	-	0.4875	48.75%
PPAR gamma	-	0.6189	61.89%
Honey bee toxicity	-	0.7396	73.96%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9829	98.29%

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	93.41%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.98%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.05%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.90%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.71%	96.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.94%	89.34%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.31%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.22%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.79%	100.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	80.19%	97.21%
CHEMBL3572	P11597	Cholesteryl ester transfer protein	80.05%	92.67%

Plants that contains it

• Arctotis fastuosa

Cross-Links

• PubChem: 163102386
• LOTUS: LTS0116470
• wikiData: Q105176559