[(5R,7R,8R,9R,10R,13S,17S)-17-[(2S,3S,5R)-5-[(2S)-3,3-dimethyloxiran-2-yl]-2-methoxyoxolan-3-yl]-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: 7a8380a3-143f-434f-9d0d-827a32a87354
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(5R,7R,8R,9R,10R,13S,17S)-17-[(2S,3S,5R)-5-[(2S)-3,3-dimethyloxiran-2-yl]-2-methoxyoxolan-3-yl]-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(CC3)C)C5CC(OC5OC)C6C(O6)(C)C)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(CC3)C)[C@@H]5C[C@@H](O[C@@H]5OC)[C@H]6C(O6)(C)C)C)C
• InChI: InChI=1S/C33H48O6/c1-18(34)37-26-17-24-29(2,3)25(35)13-15-32(24,7)23-12-14-31(6)20(10-11-22(31)33(23,26)8)19-16-21(38-28(19)36-9)27-30(4,5)39-27/h11,13,15,19-21,23-24,26-28H,10,12,14,16-17H2,1-9H3/t19-,20-,21+,23+,24-,26+,27-,28-,31-,32+,33-/m0/s1
• InChI Key: OTQGYKHVZJRPCB-HNNHISDKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₈O₆
• Molecular Weight: 540.70 g/mol
• Exact Mass: 540.34508925 g/mol
• Topological Polar Surface Area (TPSA): 74.40 Ų
• XlogP: 5.80
• Atomic LogP (AlogP): 6.03
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9928	99.28%
Caco-2	-	0.7207	72.07%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8008	80.08%
OATP2B1 inhibitior	-	0.8647	86.47%
OATP1B1 inhibitior	+	0.7795	77.95%
OATP1B3 inhibitior	+	0.9633	96.33%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.8482	84.82%
P-glycoprotein inhibitior	+	0.7819	78.19%
P-glycoprotein substrate	-	0.5390	53.90%
CYP3A4 substrate	+	0.7490	74.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8967	89.67%
CYP3A4 inhibition	+	0.5273	52.73%
CYP2C9 inhibition	-	0.7695	76.95%
CYP2C19 inhibition	-	0.8184	81.84%
CYP2D6 inhibition	-	0.9410	94.10%
CYP1A2 inhibition	-	0.7803	78.03%
CYP2C8 inhibition	+	0.7098	70.98%
CYP inhibitory promiscuity	-	0.8271	82.71%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.4381	43.81%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.9274	92.74%
Skin irritation	-	0.6388	63.88%
Skin corrosion	-	0.9105	91.05%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6774	67.74%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.8114	81.14%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	+	0.6140	61.40%
Acute Oral Toxicity (c)	III	0.3675	36.75%
Estrogen receptor binding	+	0.7695	76.95%
Androgen receptor binding	+	0.7105	71.05%
Thyroid receptor binding	+	0.5993	59.93%
Glucocorticoid receptor binding	+	0.7020	70.20%
Aromatase binding	+	0.6685	66.85%
PPAR gamma	+	0.7392	73.92%
Honey bee toxicity	-	0.7088	70.88%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9940	99.40%

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	97.82%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.10%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.50%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	93.01%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.38%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.42%	95.56%
CHEMBL340	P08684	Cytochrome P450 3A4	89.90%	91.19%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.23%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.83%	99.23%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.06%	93.04%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.67%	94.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.64%	89.00%
CHEMBL5028	O14672	ADAM10	83.45%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	83.14%	92.50%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.09%	97.14%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.90%	97.28%
CHEMBL1871	P10275	Androgen Receptor	81.18%	96.43%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	81.01%	94.08%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.99%	86.33%

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: 10414931
• NPASS: NPC54105
• LOTUS: LTS0247854
• wikiData: Q105199750