(3S,3aS,6R,6aR,8S,9aR,9bS)-6-hydroxy-3,6-dimethyl-9-methylidene-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one

Details

• Internal ID: ef694c49-a4bb-4496-8be8-ae805f1faef4
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: (3S,3aS,6R,6aR,8S,9aR,9bS)-6-hydroxy-3,6-dimethyl-9-methylidene-8-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3a,4,5,6a,7,8,9a,9b-octahydro-3H-azuleno[4,5-b]furan-2-one
• SMILES (Canonical): CC1C2CCC(C3CC(C(=C)C3C2OC1=O)OC4C(C(C(C(O4)CO)O)O)O)(C)O
• SMILES (Isomeric): C[C@H]1[C@@H]2CC[C@@]([C@@H]3C[C@@H](C(=C)[C@@H]3[C@H]2OC1=O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)(C)O
• InChI: InChI=1S/C21H32O9/c1-8-10-4-5-21(3,27)11-6-12(9(2)14(11)18(10)30-19(8)26)28-20-17(25)16(24)15(23)13(7-22)29-20/h8,10-18,20,22-25,27H,2,4-7H2,1,3H3/t8-,10-,11+,12-,13+,14-,15+,16-,17+,18-,20+,21+/m0/s1
• InChI Key: IMDGPABUKQYVEL-GUTBQPCFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₂O₉
• Molecular Weight: 428.50 g/mol
• Exact Mass: 428.20463259 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): -0.91
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8078	80.78%
Caco-2	-	0.8313	83.13%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7396	73.96%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8388	83.88%
OATP1B3 inhibitior	+	0.9469	94.69%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	-	0.8632	86.32%
P-glycoprotein inhibitior	-	0.7991	79.91%
P-glycoprotein substrate	-	0.6718	67.18%
CYP3A4 substrate	+	0.6921	69.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8960	89.60%
CYP3A4 inhibition	-	0.8922	89.22%
CYP2C9 inhibition	-	0.8234	82.34%
CYP2C19 inhibition	-	0.8799	87.99%
CYP2D6 inhibition	-	0.9307	93.07%
CYP1A2 inhibition	-	0.8209	82.09%
CYP2C8 inhibition	-	0.7109	71.09%
CYP inhibitory promiscuity	-	0.9424	94.24%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6696	66.96%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9535	95.35%
Skin irritation	-	0.5224	52.24%
Skin corrosion	-	0.9359	93.59%
Ames mutagenesis	-	0.6986	69.86%
Human Ether-a-go-go-Related Gene inhibition	-	0.6203	62.03%
Micronuclear	-	0.9000	90.00%
Hepatotoxicity	-	0.5976	59.76%
skin sensitisation	-	0.8859	88.59%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.6263	62.63%
Acute Oral Toxicity (c)	I	0.4159	41.59%
Estrogen receptor binding	+	0.6680	66.80%
Androgen receptor binding	+	0.5861	58.61%
Thyroid receptor binding	+	0.5203	52.03%
Glucocorticoid receptor binding	+	0.6180	61.80%
Aromatase binding	+	0.6063	60.63%
PPAR gamma	+	0.5341	53.41%
Honey bee toxicity	-	0.6923	69.23%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9579	95.79%

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	98.03%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.05%	91.11%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	93.35%	96.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.61%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.36%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.69%	100.00%
CHEMBL1871	P10275	Androgen Receptor	87.17%	96.43%
CHEMBL4072	P07858	Cathepsin B	86.67%	93.67%
CHEMBL226	P30542	Adenosine A1 receptor	86.20%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.12%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.44%	89.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.43%	86.92%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.92%	95.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.36%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.31%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	82.30%	92.50%
CHEMBL2581	P07339	Cathepsin D	81.84%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.71%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.66%	96.61%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.07%	97.14%

Plants that contains it

• Ixeris tamagawaensis

Cross-Links

• PubChem: 162956587
• LOTUS: LTS0189348
• wikiData: Q105115601