[(1S,2R,4S,5S,9R,10R,13R,14S,15S,17S)-9-(furan-3-yl)-1-hydroxy-15-[(1R)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.02,4.04,13.05,10]octadecan-17-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: e50cfcdd-3e1c-4787-a075-5defe3518b33
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1S,2R,4S,5S,9R,10R,13R,14S,15S,17S)-9-(furan-3-yl)-1-hydroxy-15-[(1R)-1-hydroxy-2-methoxy-2-oxoethyl]-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.02,4.04,13.05,10]octadecan-17-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C(C2(C3CCC4(C(C35C(C1(C2=O)O)O5)CC(=O)OC4C6=COC=C6)C)C)C(C(=O)OC)O)(C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1[C@@]2([C@@H]3[C@@]4(O3)[C@H](CC[C@@]5([C@@H]4CC(=O)O[C@H]5C6=COC=C6)C)[C@@](C2=O)([C@H](C1(C)C)[C@H](C(=O)OC)O)C)O
• InChI: InChI=1S/C32H40O11/c1-8-15(2)23(35)42-26-28(3,4)21(20(34)24(36)39-7)30(6)17-9-11-29(5)18(32(17)27(43-32)31(26,38)25(30)37)13-19(33)41-22(29)16-10-12-40-14-16/h8,10,12,14,17-18,20-22,26-27,34,38H,9,11,13H2,1-7H3/b15-8-/t17-,18+,20-,21+,22+,26+,27-,29-,30-,31+,32-/m1/s1
• InChI Key: OWNYIZYKHUQFKG-CJKPJILGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₀O₁₁
• Molecular Weight: 600.70 g/mol
• Exact Mass: 600.25706209 g/mol
• Topological Polar Surface Area (TPSA): 162.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.83
• H-Bond Acceptor: 11
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9782	97.82%
Caco-2	-	0.7828	78.28%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7605	76.05%
OATP2B1 inhibitior	-	0.7160	71.60%
OATP1B1 inhibitior	-	0.3545	35.45%
OATP1B3 inhibitior	+	0.9489	94.89%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9000	90.00%
P-glycoprotein inhibitior	+	0.7829	78.29%
P-glycoprotein substrate	+	0.6435	64.35%
CYP3A4 substrate	+	0.7328	73.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8840	88.40%
CYP3A4 inhibition	+	0.7458	74.58%
CYP2C9 inhibition	-	0.7720	77.20%
CYP2C19 inhibition	-	0.8043	80.43%
CYP2D6 inhibition	-	0.9203	92.03%
CYP1A2 inhibition	-	0.7629	76.29%
CYP2C8 inhibition	+	0.6803	68.03%
CYP inhibitory promiscuity	-	0.8486	84.86%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4743	47.43%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.8867	88.67%
Skin irritation	-	0.6822	68.22%
Skin corrosion	-	0.9227	92.27%
Ames mutagenesis	-	0.7070	70.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4094	40.94%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.5676	56.76%
skin sensitisation	-	0.8194	81.94%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.7695	76.95%
Acute Oral Toxicity (c)	I	0.5118	51.18%
Estrogen receptor binding	+	0.7599	75.99%
Androgen receptor binding	+	0.7304	73.04%
Thyroid receptor binding	+	0.5930	59.30%
Glucocorticoid receptor binding	+	0.8165	81.65%
Aromatase binding	+	0.6886	68.86%
PPAR gamma	+	0.7268	72.68%
Honey bee toxicity	-	0.6214	62.14%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9937	99.37%

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	99.23%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.64%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	97.58%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.14%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.56%	89.00%
CHEMBL2581	P07339	Cathepsin D	91.36%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.15%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.53%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.55%	85.14%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.25%	91.24%
CHEMBL340	P08684	Cytochrome P450 3A4	87.72%	91.19%
CHEMBL3524	P56524	Histone deacetylase 4	85.61%	92.97%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	85.16%	89.67%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.56%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.54%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.26%	97.14%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	83.24%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.08%	93.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.06%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.43%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.21%	99.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.20%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.16%	95.71%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.70%	92.88%
CHEMBL3437	Q16853	Amine oxidase, copper containing	81.63%	94.00%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	81.35%	80.00%
CHEMBL3038469	P24941	CDK2/Cyclin A	80.64%	91.38%

Plants that contains it

• Swietenia mahagoni

Cross-Links

• PubChem: 162909379
• LOTUS: LTS0070675
• wikiData: Q105202156