2-[(3R,3aR,6aR,8R,9aR,9bR)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-8-yl]acetic acid

Details

• Internal ID: 63ec6ff1-c3c7-4455-a0a0-b4d85543b073
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 2-[(3R,3aR,6aR,8R,9aR,9bR)-3,8-dihydroxy-3-(hydroxymethyl)-6,9-dimethylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-8-yl]acetic acid
• SMILES (Canonical): C=C1CCC2C(C3C1CC(C3=C)(CC(=O)O)O)OC(=O)C2(CO)O
• SMILES (Isomeric): C=C1CC[C@@H]2[C@@H]([C@@H]3[C@H]1C[C@](C3=C)(CC(=O)O)O)OC(=O)[C@@]2(CO)O
• InChI: InChI=1S/C17H22O7/c1-8-3-4-11-14(24-15(21)17(11,23)7-18)13-9(2)16(22,5-10(8)13)6-12(19)20/h10-11,13-14,18,22-23H,1-7H2,(H,19,20)/t10-,11+,13-,14-,16+,17-/m0/s1
• InChI Key: OXUUEDHJHFWUCB-KPSPPPMPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₂O₇
• Molecular Weight: 338.40 g/mol
• Exact Mass: 338.13655304 g/mol
• Topological Polar Surface Area (TPSA): 124.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.00
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7706	77.06%
Caco-2	-	0.7929	79.29%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6606	66.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8811	88.11%
OATP1B3 inhibitior	+	0.9627	96.27%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7314	73.14%
BSEP inhibitior	-	0.9436	94.36%
P-glycoprotein inhibitior	-	0.8950	89.50%
P-glycoprotein substrate	-	0.8003	80.03%
CYP3A4 substrate	+	0.5749	57.49%
CYP2C9 substrate	+	0.6031	60.31%
CYP2D6 substrate	-	0.8573	85.73%
CYP3A4 inhibition	-	0.9302	93.02%
CYP2C9 inhibition	-	0.8300	83.00%
CYP2C19 inhibition	-	0.8421	84.21%
CYP2D6 inhibition	-	0.9172	91.72%
CYP1A2 inhibition	-	0.8433	84.33%
CYP2C8 inhibition	-	0.6912	69.12%
CYP inhibitory promiscuity	-	0.9762	97.62%
UGT catelyzed	+	0.5362	53.62%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6657	66.57%
Eye corrosion	-	0.9785	97.85%
Eye irritation	-	0.7036	70.36%
Skin irritation	-	0.6838	68.38%
Skin corrosion	-	0.9304	93.04%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6923	69.23%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.8697	86.97%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.5375	53.75%
Acute Oral Toxicity (c)	III	0.4566	45.66%
Estrogen receptor binding	+	0.7195	71.95%
Androgen receptor binding	+	0.5642	56.42%
Thyroid receptor binding	-	0.5168	51.68%
Glucocorticoid receptor binding	+	0.7816	78.16%
Aromatase binding	-	0.4844	48.44%
PPAR gamma	-	0.5460	54.60%
Honey bee toxicity	-	0.8871	88.71%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.8526	85.26%

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	95.14%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.10%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.37%	85.14%
CHEMBL221	P23219	Cyclooxygenase-1	89.23%	90.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.12%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.84%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	84.10%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.90%	95.56%
CHEMBL218	P21554	Cannabinoid CB1 receptor	82.21%	96.61%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.94%	100.00%

Plants that contains it

• Centaurea solstitialis

Cross-Links

• PubChem: 101626736
• LOTUS: LTS0202178
• wikiData: Q105202952