[(5R,7R,8R,9R,10S,11R,13S,17S)-17-[(2S,3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-11-hydroxy-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-yl] acetate

Details

• Internal ID: 1811ed2a-7125-44f5-a438-948dda8f6229
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(5R,7R,8R,9R,10S,11R,13S,17S)-17-[(2S,3S,5R)-5-[(1S)-1,2-dihydroxy-2-methylpropyl]-2-methoxyoxolan-3-yl]-11-hydroxy-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-7-yl] acetate
• SMILES (Canonical): CC(=O)OC1CC2C(C(=O)C=CC2(C3C1(C4=CCC(C4(CC3O)C)C5CC(OC5OC)C(C(C)(C)O)O)C)C)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@](C=CC(=O)C2(C)C)([C@@H]3[C@@]1(C4=CC[C@H]([C@@]4(C[C@H]3O)C)[C@@H]5C[C@@H](O[C@@H]5OC)[C@@H](C(C)(C)O)O)C)C
• InChI: InChI=1S/C33H50O8/c1-17(34)40-25-15-23-29(2,3)24(36)12-13-31(23,6)26-20(35)16-32(7)19(10-11-22(32)33(25,26)8)18-14-21(41-28(18)39-9)27(37)30(4,5)38/h11-13,18-21,23,25-28,35,37-38H,10,14-16H2,1-9H3/t18-,19-,20+,21+,23-,25+,26+,27-,28-,31-,32-,33+/m0/s1
• InChI Key: CPDZEWXZPRHIGS-ZGXZVTMDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₀O₈
• Molecular Weight: 574.70 g/mol
• Exact Mass: 574.35056855 g/mol
• Topological Polar Surface Area (TPSA): 123.00 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.96
• H-Bond Acceptor: 8
• 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	+	0.9892	98.92%
Caco-2	-	0.7946	79.46%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7746	77.46%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8172	81.72%
OATP1B3 inhibitior	+	0.9053	90.53%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7783	77.83%
P-glycoprotein inhibitior	+	0.6841	68.41%
P-glycoprotein substrate	+	0.6365	63.65%
CYP3A4 substrate	+	0.7429	74.29%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9028	90.28%
CYP3A4 inhibition	-	0.5213	52.13%
CYP2C9 inhibition	-	0.7357	73.57%
CYP2C19 inhibition	-	0.7732	77.32%
CYP2D6 inhibition	-	0.9430	94.30%
CYP1A2 inhibition	-	0.8201	82.01%
CYP2C8 inhibition	+	0.6460	64.60%
CYP inhibitory promiscuity	-	0.9135	91.35%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.4564	45.64%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9312	93.12%
Skin irritation	-	0.5900	59.00%
Skin corrosion	-	0.9339	93.39%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4366	43.66%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.5552	55.52%
skin sensitisation	-	0.8294	82.94%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.5980	59.80%
Acute Oral Toxicity (c)	I	0.6547	65.47%
Estrogen receptor binding	+	0.7238	72.38%
Androgen receptor binding	+	0.7032	70.32%
Thyroid receptor binding	+	0.5433	54.33%
Glucocorticoid receptor binding	+	0.6891	68.91%
Aromatase binding	+	0.6802	68.02%
PPAR gamma	+	0.6771	67.71%
Honey bee toxicity	-	0.6169	61.69%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9950	99.50%

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	99.70%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.14%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.83%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.90%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.02%	97.25%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.04%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	91.47%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.68%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.35%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.22%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	89.06%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.23%	91.07%
CHEMBL3401	O75469	Pregnane X receptor	88.07%	94.73%
CHEMBL2581	P07339	Cathepsin D	86.84%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.77%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.14%	86.33%
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	84.46%	88.84%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.35%	93.04%
CHEMBL5028	O14672	ADAM10	84.24%	97.50%
CHEMBL2179	P04062	Beta-glucocerebrosidase	83.59%	85.31%
CHEMBL259	P32245	Melanocortin receptor 4	83.10%	95.38%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.46%	89.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.12%	94.08%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.63%	94.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	80.28%	97.28%

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: 71544782
• NPASS: NPC246664