(3aS,6S,6aR,9aR,9bS)-6-methyl-3-methylidene-9-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4,5,6,6a,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2,7-dione

Details

• Internal ID: 40558556-61a1-4902-a7eb-818738e43f37
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3aS,6S,6aR,9aR,9bS)-6-methyl-3-methylidene-9-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-4,5,6,6a,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2,7-dione
• InChI: InChI=1S/C21H28O9/c1-8-3-4-11-9(2)20(27)30-19(11)15-10(5-12(23)14(8)15)7-28-21-18(26)17(25)16(24)13(6-22)29-21/h5,8,11,13-19,21-22,24-26H,2-4,6-7H2,1H3/t8-,11-,13+,14-,15-,16+,17-,18+,19-,21+/m0/s1
• InChI Key: AWUZOKJLIBMIIC-HLKMIBDASA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₈O₉
• Molecular Weight: 424.40 g/mol
• Exact Mass: 424.17333247 g/mol
• Topological Polar Surface Area (TPSA): 143.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -0.93
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6003	60.03%
Caco-2	-	0.8090	80.90%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7352	73.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8151	81.51%
OATP1B3 inhibitior	+	0.9448	94.48%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.5780	57.80%
P-glycoprotein inhibitior	-	0.7479	74.79%
P-glycoprotein substrate	-	0.7268	72.68%
CYP3A4 substrate	+	0.6277	62.77%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.8999	89.99%
CYP3A4 inhibition	-	0.9375	93.75%
CYP2C9 inhibition	-	0.8440	84.40%
CYP2C19 inhibition	-	0.8220	82.20%
CYP2D6 inhibition	-	0.9070	90.70%
CYP1A2 inhibition	-	0.7873	78.73%
CYP2C8 inhibition	+	0.4668	46.68%
CYP inhibitory promiscuity	-	0.9059	90.59%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6944	69.44%
Eye corrosion	-	0.9823	98.23%
Eye irritation	-	0.9637	96.37%
Skin irritation	-	0.7214	72.14%
Skin corrosion	-	0.9240	92.40%
Ames mutagenesis	-	0.6808	68.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.6480	64.80%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5665	56.65%
skin sensitisation	-	0.8667	86.67%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	+	0.5668	56.68%
Acute Oral Toxicity (c)	III	0.5012	50.12%
Estrogen receptor binding	+	0.6646	66.46%
Androgen receptor binding	+	0.7091	70.91%
Thyroid receptor binding	-	0.6157	61.57%
Glucocorticoid receptor binding	-	0.4826	48.26%
Aromatase binding	-	0.4824	48.24%
PPAR gamma	+	0.5321	53.21%
Honey bee toxicity	-	0.7934	79.34%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6050	60.50%
Fish aquatic toxicity	+	0.8717	87.17%

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	97.72%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	94.26%	95.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.55%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.22%	97.09%
CHEMBL2581	P07339	Cathepsin D	92.06%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.53%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.27%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.61%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.41%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.86%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.08%	95.89%

Plants that contains it

• Scorzoneroides atlantica

Cross-Links

• PubChem: 10550250
• LOTUS: LTS0004283
• wikiData: Q104920296