[(5R,7R,8R,9R,10R,12S,13S,14S,17S)-12-hydroxy-17-[(3R)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-7-yl] (E)-3-(4-acetyloxy-3-methoxyphenyl)prop-2-enoate

Details

• Internal ID: b68e5ebf-b583-4c7a-9a66-2fcbd50bb4ee
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(5R,7R,8R,9R,10R,12S,13S,14S,17S)-12-hydroxy-17-[(3R)-2-hydroxy-5-(hydroxymethyl)oxolan-3-yl]-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-7-yl] (E)-3-(4-acetyloxy-3-methoxyphenyl)prop-2-enoate
• SMILES (Canonical): CC(=O)OC1=C(C=C(C=C1)C=CC(=O)OC2CC3C(C(=O)C=CC3(C4C2(C5CCC(C5(C(C4)O)C)C6CC(OC6O)CO)C)C)(C)C)OC
• SMILES (Isomeric): CC(=O)OC1=C(C=C(C=C1)/C=C/C(=O)O[C@@H]2C[C@@H]3[C@](C=CC(=O)C3(C)C)([C@@H]4[C@@]2([C@H]5CC[C@H]([C@@]5([C@H](C4)O)C)[C@H]6CC(OC6O)CO)C)C)OC
• InChI: InChI=1S/C39H52O10/c1-21(41)47-26-11-8-22(16-27(26)46-7)9-13-34(44)49-33-19-29-36(2,3)31(42)14-15-37(29,4)30-18-32(43)38(5)25(10-12-28(38)39(30,33)6)24-17-23(20-40)48-35(24)45/h8-9,11,13-16,23-25,28-30,32-33,35,40,43,45H,10,12,17-20H2,1-7H3/b13-9+/t23?,24-,25+,28+,29+,30-,32+,33-,35?,37+,38+,39+/m1/s1
• InChI Key: IWNRAUGSDDNDEH-AWBOYJDTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₉H₅₂O₁₀
• Molecular Weight: 680.80 g/mol
• Exact Mass: 680.35604785 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 5.50
• Atomic LogP (AlogP): 4.87
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9890	98.90%
Caco-2	-	0.8448	84.48%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8649	86.49%
OATP2B1 inhibitior	-	0.8561	85.61%
OATP1B1 inhibitior	+	0.8411	84.11%
OATP1B3 inhibitior	+	0.8747	87.47%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.8157	81.57%
BSEP inhibitior	+	0.9451	94.51%
P-glycoprotein inhibitior	+	0.7660	76.60%
P-glycoprotein substrate	+	0.6934	69.34%
CYP3A4 substrate	+	0.7368	73.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8711	87.11%
CYP3A4 inhibition	+	0.8408	84.08%
CYP2C9 inhibition	-	0.6438	64.38%
CYP2C19 inhibition	-	0.7730	77.30%
CYP2D6 inhibition	-	0.9187	91.87%
CYP1A2 inhibition	-	0.6179	61.79%
CYP2C8 inhibition	+	0.8352	83.52%
CYP inhibitory promiscuity	-	0.6238	62.38%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9100	91.00%
Carcinogenicity (trinary)	Non-required	0.5862	58.62%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9222	92.22%
Skin irritation	-	0.7454	74.54%
Skin corrosion	-	0.9510	95.10%
Ames mutagenesis	-	0.7271	72.71%
Human Ether-a-go-go-Related Gene inhibition	+	0.7932	79.32%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.6198	61.98%
skin sensitisation	-	0.9025	90.25%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.8734	87.34%
Acute Oral Toxicity (c)	III	0.3106	31.06%
Estrogen receptor binding	+	0.8044	80.44%
Androgen receptor binding	+	0.7323	73.23%
Thyroid receptor binding	+	0.5845	58.45%
Glucocorticoid receptor binding	+	0.7707	77.07%
Aromatase binding	+	0.6150	61.50%
PPAR gamma	+	0.7717	77.17%
Honey bee toxicity	-	0.6511	65.11%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9901	99.01%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.63%	86.33%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.62%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.67%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.15%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.87%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.63%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.88%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.04%	97.09%
CHEMBL3922	P50579	Methionine aminopeptidase 2	91.36%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.40%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.88%	95.56%
CHEMBL2581	P07339	Cathepsin D	88.54%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.21%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.97%	92.94%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.89%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.81%	97.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.49%	92.62%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	86.39%	91.07%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	85.90%	92.38%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.59%	95.89%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.83%	97.33%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.48%	95.50%
CHEMBL1937	Q92769	Histone deacetylase 2	83.21%	94.75%
CHEMBL5028	O14672	ADAM10	81.47%	97.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.39%	93.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	80.77%	96.95%

Plants that contains it

• Azadirachta indica

Cross-Links

• PubChem: 101153492
• LOTUS: LTS0044280
• wikiData: Q104667111