(1R,2S,3R,6R,8S,9S,13S,14R,15R,16S,17R)-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-11-ene-17-carboxylic acid

Details

• Internal ID: 28605a6d-2b03-45c8-90ac-964227626979
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: (1R,2S,3R,6R,8S,9S,13S,14R,15R,16S,17R)-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-15,16-dihydroxy-9,13-dimethyl-4,10-dioxo-11-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-11-ene-17-carboxylic acid
• SMILES (Canonical): CC1C2CC3C45COC(C4C(C(=O)O3)OC(=O)C=C(C)C(C)C)(C(C(C5C2(C=C(C1=O)OC6C(C(C(C(O6)CO)O)O)O)C)O)O)C(=O)O
• SMILES (Isomeric): C[C@H]1[C@@H]2C[C@@H]3[C@@]45CO[C@]([C@@H]4[C@H](C(=O)O3)OC(=O)/C=C(\C)/C(C)C)([C@H]([C@@H]([C@@H]5[C@]2(C=C(C1=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)O)O)C(=O)O
• InChI: InChI=1S/C33H44O16/c1-11(2)12(3)6-18(35)49-24-26-32-10-45-33(26,30(43)44)27(41)23(40)25(32)31(5)8-15(19(36)13(4)14(31)7-17(32)48-28(24)42)46-29-22(39)21(38)20(37)16(9-34)47-29/h6,8,11,13-14,16-17,20-27,29,34,37-41H,7,9-10H2,1-5H3,(H,43,44)/b12-6+/t13-,14-,16+,17+,20+,21-,22+,23+,24+,25+,26+,27-,29+,31-,32+,33+/m0/s1
• InChI Key: QKJUIIHWGAGPPI-OCRPBTDZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₄O₁₆
• Molecular Weight: 696.70 g/mol
• Exact Mass: 696.26293531 g/mol
• Topological Polar Surface Area (TPSA): 256.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -1.82
• H-Bond Acceptor: 15
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7113	71.13%
Caco-2	-	0.8753	87.53%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7832	78.32%
OATP2B1 inhibitior	-	0.8612	86.12%
OATP1B1 inhibitior	+	0.8215	82.15%
OATP1B3 inhibitior	+	0.9267	92.67%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7778	77.78%
P-glycoprotein inhibitior	+	0.6979	69.79%
P-glycoprotein substrate	+	0.7159	71.59%
CYP3A4 substrate	+	0.7081	70.81%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8904	89.04%
CYP3A4 inhibition	-	0.9007	90.07%
CYP2C9 inhibition	-	0.8272	82.72%
CYP2C19 inhibition	-	0.8543	85.43%
CYP2D6 inhibition	-	0.9341	93.41%
CYP1A2 inhibition	-	0.8829	88.29%
CYP2C8 inhibition	+	0.6394	63.94%
CYP inhibitory promiscuity	-	0.8456	84.56%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6074	60.74%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9174	91.74%
Skin irritation	-	0.6909	69.09%
Skin corrosion	-	0.9328	93.28%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6914	69.14%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.8500	85.00%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5733	57.33%
Acute Oral Toxicity (c)	III	0.6314	63.14%
Estrogen receptor binding	+	0.7943	79.43%
Androgen receptor binding	+	0.7252	72.52%
Thyroid receptor binding	-	0.5133	51.33%
Glucocorticoid receptor binding	+	0.7113	71.13%
Aromatase binding	+	0.6828	68.28%
PPAR gamma	+	0.7268	72.68%
Honey bee toxicity	-	0.6267	62.67%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9520	95.20%

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	99.16%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.28%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.27%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.95%	85.14%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	94.71%	89.34%
CHEMBL2581	P07339	Cathepsin D	93.05%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.90%	86.33%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	90.90%	96.47%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.42%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.41%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.29%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.14%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	87.08%	95.93%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.14%	91.07%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.74%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	82.93%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.60%	96.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.41%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.23%	95.89%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.87%	82.50%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.58%	89.50%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.39%	95.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.93%	98.75%
CHEMBL2996	Q05655	Protein kinase C delta	80.71%	97.79%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.57%	97.28%
CHEMBL5028	O14672	ADAM10	80.23%	97.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.13%	91.24%

Plants that contains it

• Asplenium normale
• Brucea javanica
• Carpobrotus edulis
• Castanea crenata
• Centrolobium tomentosum
• Ceratophyllum submersum
• Dracocephalum kotschyi
• Lippia carviodora
• Myrica nana
• Psilostrophe cooperi
• Sideritis tragoriganum
• Solanum jamaicense
• Trifolium alexandrinum

Cross-Links

• PubChem: 10556620
• NPASS: NPC205955
• LOTUS: LTS0128025
• wikiData: Q105223172