[(1R,2R,3S,7S,8R,10R,11R,15S,16S,17R)-3-acetyloxy-15-(furan-3-yl)-7-(hydroxymethyl)-10-[(2R,3R)-2-hydroxy-3-methylpentanoyl]oxy-2,7,11,16-tetramethyl-5-oxo-6-oxatetracyclo[9.7.0.02,8.012,16]octadec-12-en-17-yl] (2R,3S)-2-hydroxy-3-methylpentanoate

Details

• Internal ID: 978622b3-3f1f-4739-a46d-4923dbec96b0
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1R,2R,3S,7S,8R,10R,11R,15S,16S,17R)-3-acetyloxy-15-(furan-3-yl)-7-(hydroxymethyl)-10-[(2R,3R)-2-hydroxy-3-methylpentanoyl]oxy-2,7,11,16-tetramethyl-5-oxo-6-oxatetracyclo[9.7.0.02,8.012,16]octadec-12-en-17-yl] (2R,3S)-2-hydroxy-3-methylpentanoate
• SMILES (Canonical): CCC(C)C(C(=O)OC1CC2C3(C(CC(C2(C4=CCC(C14C)C5=COC=C5)C)OC(=O)C(C(C)CC)O)C(OC(=O)CC3OC(=O)C)(C)CO)C)O
• SMILES (Isomeric): CC[C@H](C)[C@H](C(=O)O[C@@H]1C[C@@H]2[C@@]3([C@@H](C[C@H]([C@]2(C4=CC[C@H]([C@]14C)C5=COC=C5)C)OC(=O)[C@@H]([C@H](C)CC)O)[C@@](OC(=O)C[C@@H]3OC(=O)C)(C)CO)C)O
• InChI: InChI=1S/C40H58O12/c1-10-21(3)33(44)35(46)50-29-17-28-39(8,26-13-12-25(38(26,29)7)24-14-15-48-19-24)30(51-36(47)34(45)22(4)11-2)16-27-37(6,20-41)52-32(43)18-31(40(27,28)9)49-23(5)42/h13-15,19,21-22,25,27-31,33-34,41,44-45H,10-12,16-18,20H2,1-9H3/t21-,22+,25-,27-,28-,29+,30+,31-,33+,34+,37+,38-,39-,40-/m0/s1
• InChI Key: XAITXSGSAXCMGO-VMDQYDODSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₅₈O₁₂
• Molecular Weight: 730.90 g/mol
• Exact Mass: 730.39282728 g/mol
• Topological Polar Surface Area (TPSA): 179.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.02
• H-Bond Acceptor: 12
• H-Bond Donor: 3
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9922	99.22%
Caco-2	-	0.8349	83.49%
Blood Brain Barrier	+	0.7250	72.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7781	77.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3448	34.48%
OATP1B3 inhibitior	+	0.8847	88.47%
MATE1 inhibitior	-	0.8812	88.12%
OCT2 inhibitior	-	0.8364	83.64%
BSEP inhibitior	+	0.9870	98.70%
P-glycoprotein inhibitior	+	0.7878	78.78%
P-glycoprotein substrate	+	0.6211	62.11%
CYP3A4 substrate	+	0.6988	69.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8371	83.71%
CYP3A4 inhibition	+	0.7417	74.17%
CYP2C9 inhibition	-	0.6596	65.96%
CYP2C19 inhibition	-	0.7843	78.43%
CYP2D6 inhibition	-	0.9449	94.49%
CYP1A2 inhibition	-	0.7982	79.82%
CYP2C8 inhibition	+	0.6877	68.77%
CYP inhibitory promiscuity	-	0.5397	53.97%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Danger	0.4522	45.22%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9126	91.26%
Skin irritation	-	0.5636	56.36%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	-	0.6491	64.91%
Human Ether-a-go-go-Related Gene inhibition	-	0.3636	36.36%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.6235	62.35%
skin sensitisation	-	0.8973	89.73%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6078	60.78%
Acute Oral Toxicity (c)	III	0.3990	39.90%
Estrogen receptor binding	+	0.7601	76.01%
Androgen receptor binding	+	0.7430	74.30%
Thyroid receptor binding	+	0.5599	55.99%
Glucocorticoid receptor binding	+	0.7952	79.52%
Aromatase binding	+	0.6651	66.51%
PPAR gamma	+	0.7614	76.14%
Honey bee toxicity	-	0.7268	72.68%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.40%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.47%	94.45%
CHEMBL2581	P07339	Cathepsin D	97.37%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.14%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.14%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.72%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.26%	89.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.70%	97.25%
CHEMBL4040	P28482	MAP kinase ERK2	88.23%	83.82%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.16%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	86.58%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.98%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.48%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.77%	94.00%
CHEMBL202	P00374	Dihydrofolate reductase	84.46%	89.92%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.46%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.37%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.16%	99.17%
CHEMBL2996	Q05655	Protein kinase C delta	81.01%	97.79%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.18%	96.00%

Plants that contains it

• Trichilia emetica

Cross-Links

• PubChem: 163027126
• LOTUS: LTS0176653
• wikiData: Q105323943