methyl (1R,2S,3R,6R,8S,9S,10R,13S,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadecane-17-carboxylate

Details

• Internal ID: 08a0a688-6b55-4e15-bf8c-8ef39153fbbf
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Quassinoids
• IUPAC Name: methyl (1R,2S,3R,6R,8S,9S,10R,13S,14R,15R,16S,17S)-3-[(E)-4-acetyloxy-3,4-dimethylpent-2-enoyl]oxy-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadecane-17-carboxylate
• SMILES (Canonical): CC1C2CC3C45COC(C4C(C(=O)O3)OC(=O)C=C(C)C(C)(C)OC(=O)C)(C(C(C5C2(CC(=O)C1O)C)O)O)C(=O)OC
• 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)OC(=O)C)([C@H]([C@@H]([C@@H]5[C@]2(CC(=O)[C@@H]1O)C)O)O)C(=O)OC
• InChI: InChI=1S/C30H40O13/c1-12(27(4,5)43-14(3)31)8-18(33)42-21-23-29-11-40-30(23,26(38)39-7)24(36)20(35)22(29)28(6)10-16(32)19(34)13(2)15(28)9-17(29)41-25(21)37/h8,13,15,17,19-24,34-36H,9-11H2,1-7H3/b12-8+/t13-,15-,17+,19+,20+,21+,22+,23+,24-,28-,29+,30-/m0/s1
• InChI Key: BQLTVAOKAIIXRW-FPWVZODWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₀O₁₃
• Molecular Weight: 608.60 g/mol
• Exact Mass: 608.24689133 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 0.00
• H-Bond Acceptor: 13
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9461	94.61%
Caco-2	-	0.8299	82.99%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8150	81.50%
OATP2B1 inhibitior	-	0.8616	86.16%
OATP1B1 inhibitior	+	0.8409	84.09%
OATP1B3 inhibitior	+	0.9194	91.94%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9105	91.05%
P-glycoprotein inhibitior	+	0.7681	76.81%
P-glycoprotein substrate	+	0.8250	82.50%
CYP3A4 substrate	+	0.7260	72.60%
CYP2C9 substrate	-	0.8253	82.53%
CYP2D6 substrate	-	0.8954	89.54%
CYP3A4 inhibition	-	0.7852	78.52%
CYP2C9 inhibition	-	0.7951	79.51%
CYP2C19 inhibition	-	0.8467	84.67%
CYP2D6 inhibition	-	0.9413	94.13%
CYP1A2 inhibition	-	0.8327	83.27%
CYP2C8 inhibition	+	0.5910	59.10%
CYP inhibitory promiscuity	-	0.9291	92.91%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5617	56.17%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9159	91.59%
Skin irritation	-	0.6481	64.81%
Skin corrosion	-	0.9390	93.90%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6107	61.07%
Micronuclear	-	0.6400	64.00%
Hepatotoxicity	+	0.6625	66.25%
skin sensitisation	-	0.8465	84.65%
Respiratory toxicity	+	0.8111	81.11%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.6878	68.78%
Acute Oral Toxicity (c)	I	0.4133	41.33%
Estrogen receptor binding	+	0.7688	76.88%
Androgen receptor binding	+	0.7211	72.11%
Thyroid receptor binding	-	0.4874	48.74%
Glucocorticoid receptor binding	+	0.7807	78.07%
Aromatase binding	+	0.7296	72.96%
PPAR gamma	+	0.6999	69.99%
Honey bee toxicity	-	0.5702	57.02%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.6600	66.00%
Fish aquatic toxicity	+	0.9895	98.95%

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	98.29%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.86%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.13%	97.25%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	95.34%	89.34%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.34%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.13%	96.77%
CHEMBL2581	P07339	Cathepsin D	93.18%	98.95%
CHEMBL299	P17252	Protein kinase C alpha	91.02%	98.03%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	90.96%	91.07%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	89.33%	95.71%
CHEMBL2996	Q05655	Protein kinase C delta	89.28%	97.79%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.92%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	88.72%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.97%	95.56%
CHEMBL2413	P32246	C-C chemokine receptor type 1	87.56%	89.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	87.38%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.37%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.23%	86.33%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.09%	95.71%
CHEMBL1902	P62942	FK506-binding protein 1A	85.44%	97.05%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.02%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.79%	96.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.66%	97.14%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	84.54%	90.93%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.31%	99.23%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.69%	94.33%
CHEMBL5028	O14672	ADAM10	82.58%	97.50%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.22%	97.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.93%	97.09%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.83%	93.04%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.54%	95.89%

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: 101499202
• NPASS: NPC255352