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

Details

• Internal ID: f9d2a987-e9e0-4065-bb0e-1d5e93429145
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Ambrosanolides and secoambrosanolides
• IUPAC Name: (3aS,6S,6aR,7R,9aS,9bR)-6a,7-dihydroxy-6,9a-dimethyl-3-methylidene-4,5,6,7,8,9b-hexahydro-3aH-azuleno[8,7-b]furan-2,9-dione
• InChI: InChI=1S/C15H20O5/c1-7-4-5-9-8(2)13(18)20-12(9)14(3)10(16)6-11(17)15(7,14)19/h7,9,11-12,17,19H,2,4-6H2,1,3H3/t7-,9-,11+,12+,14-,15-/m0/s1
• InChI Key: YAPWFHYBVVSYKK-PUUYIXGTSA-N
• Popularity: 1 reference 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): 83.80 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.59
• H-Bond Acceptor: 5
• 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	+	0.9454	94.54%
Caco-2	-	0.5317	53.17%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6157	61.57%
OATP2B1 inhibitior	-	0.8544	85.44%
OATP1B1 inhibitior	+	0.9071	90.71%
OATP1B3 inhibitior	+	0.9064	90.64%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7342	73.42%
BSEP inhibitior	-	0.9434	94.34%
P-glycoprotein inhibitior	-	0.8764	87.64%
P-glycoprotein substrate	-	0.8076	80.76%
CYP3A4 substrate	+	0.5727	57.27%
CYP2C9 substrate	-	0.7947	79.47%
CYP2D6 substrate	-	0.8842	88.42%
CYP3A4 inhibition	-	0.7176	71.76%
CYP2C9 inhibition	-	0.7470	74.70%
CYP2C19 inhibition	-	0.7272	72.72%
CYP2D6 inhibition	-	0.9348	93.48%
CYP1A2 inhibition	+	0.5098	50.98%
CYP2C8 inhibition	-	0.8398	83.98%
CYP inhibitory promiscuity	-	0.9812	98.12%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5530	55.30%
Eye corrosion	-	0.9850	98.50%
Eye irritation	-	0.9100	91.00%
Skin irritation	+	0.5261	52.61%
Skin corrosion	-	0.8442	84.42%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8077	80.77%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	+	0.7292	72.92%
skin sensitisation	-	0.7966	79.66%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.9125	91.25%
Nephrotoxicity	+	0.8141	81.41%
Acute Oral Toxicity (c)	II	0.2916	29.16%
Estrogen receptor binding	+	0.7119	71.19%
Androgen receptor binding	+	0.5783	57.83%
Thyroid receptor binding	-	0.5590	55.90%
Glucocorticoid receptor binding	+	0.5512	55.12%
Aromatase binding	+	0.5845	58.45%
PPAR gamma	-	0.5373	53.73%
Honey bee toxicity	-	0.8982	89.82%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9729	97.29%

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	96.46%	85.14%
CHEMBL1902	P62942	FK506-binding protein 1A	89.63%	97.05%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	89.23%	91.11%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.83%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.43%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.35%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.37%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.54%	92.94%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.36%	93.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.86%	100.00%
CHEMBL2581	P07339	Cathepsin D	81.04%	98.95%

Plants that contains it

• Parthenium hysterophorus

Cross-Links

• PubChem: 13967192
• LOTUS: LTS0250005
• wikiData: Q103785323