[(5R,5aR,8aS,9aS)-8,9-dihydroxy-5-methyl-1-methylidene-2-oxo-3a,4,5,5a,6,7,8,8a,9,9a-decahydroazuleno[6,5-b]furan-6-yl] 2-hydroxypropanoate

Details

• Internal ID: f96bebc3-e9fd-4cef-859e-c6d92c6ca82c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones
• IUPAC Name: [(5R,5aR,8aS,9aS)-8,9-dihydroxy-5-methyl-1-methylidene-2-oxo-3a,4,5,5a,6,7,8,8a,9,9a-decahydroazuleno[6,5-b]furan-6-yl] 2-hydroxypropanoate
• SMILES (Canonical): CC1CC2C(C(C3C1C(CC3O)OC(=O)C(C)O)O)C(=C)C(=O)O2
• SMILES (Isomeric): C[C@@H]1CC2[C@H](C([C@H]3[C@@H]1C(CC3O)OC(=O)C(C)O)O)C(=C)C(=O)O2
• InChI: InChI=1S/C17H24O7/c1-6-4-10-13(7(2)16(21)23-10)15(20)14-9(19)5-11(12(6)14)24-17(22)8(3)18/h6,8-15,18-20H,2,4-5H2,1,3H3/t6-,8?,9?,10?,11?,12+,13-,14-,15?/m1/s1
• InChI Key: SPGPYRMOKKXERI-IHEIEKSGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₄O₇
• Molecular Weight: 340.40 g/mol
• Exact Mass: 340.15220310 g/mol
• Topological Polar Surface Area (TPSA): 113.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -0.23
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9041	90.41%
Caco-2	-	0.6628	66.28%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.4941	49.41%
OATP2B1 inhibitior	-	0.8574	85.74%
OATP1B1 inhibitior	+	0.8923	89.23%
OATP1B3 inhibitior	+	0.9363	93.63%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9823	98.23%
P-glycoprotein inhibitior	-	0.8287	82.87%
P-glycoprotein substrate	-	0.8017	80.17%
CYP3A4 substrate	+	0.6187	61.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8765	87.65%
CYP3A4 inhibition	-	0.6816	68.16%
CYP2C9 inhibition	-	0.8325	83.25%
CYP2C19 inhibition	-	0.7841	78.41%
CYP2D6 inhibition	-	0.9222	92.22%
CYP1A2 inhibition	-	0.7521	75.21%
CYP2C8 inhibition	-	0.8403	84.03%
CYP inhibitory promiscuity	-	0.8769	87.69%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5665	56.65%
Eye corrosion	-	0.9757	97.57%
Eye irritation	-	0.8650	86.50%
Skin irritation	-	0.6542	65.42%
Skin corrosion	-	0.9176	91.76%
Ames mutagenesis	-	0.6954	69.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.6254	62.54%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	+	0.6875	68.75%
skin sensitisation	-	0.7760	77.60%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.6023	60.23%
Acute Oral Toxicity (c)	II	0.3341	33.41%
Estrogen receptor binding	+	0.7667	76.67%
Androgen receptor binding	-	0.5295	52.95%
Thyroid receptor binding	+	0.5857	58.57%
Glucocorticoid receptor binding	+	0.7816	78.16%
Aromatase binding	+	0.5439	54.39%
PPAR gamma	+	0.5207	52.07%
Honey bee toxicity	-	0.7073	70.73%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9551	95.51%

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	97.51%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.29%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.54%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.15%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	91.58%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.50%	96.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.21%	96.47%
CHEMBL2581	P07339	Cathepsin D	89.47%	98.95%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	88.96%	95.71%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.04%	99.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.55%	97.09%
CHEMBL299	P17252	Protein kinase C alpha	86.06%	98.03%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.02%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.91%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	83.63%	97.79%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.17%	97.14%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.16%	91.07%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	82.73%	93.03%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.26%	95.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.47%	93.56%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.33%	98.75%

Plants that contains it

• Helenium donianum

Cross-Links

• PubChem: 101306696
• LOTUS: LTS0268331
• wikiData: Q104401961