3-[[(3R,5R,8R,9R,10R,12R,13R,14R,17R)-12-acetyloxy-17-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-1,2,3,5,6,7,9,11,12,13,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]-3-oxopropanoic acid

Details

• Internal ID: eeac7bee-da37-45cf-a381-8af1f65ddc8a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: 3-[[(3R,5R,8R,9R,10R,12R,13R,14R,17R)-12-acetyloxy-17-hydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-1,2,3,5,6,7,9,11,12,13,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]-3-oxopropanoic acid
• SMILES (Canonical): CC(=CCCC(C)(C1(CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)OC(=O)CC(=O)O)C)C)OC(=O)C)C)O)O)C
• SMILES (Isomeric): CC(=CCC[C@@](C)([C@]1(CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@H](C4(C)C)OC(=O)CC(=O)O)C)C)OC(=O)C)C)O)O)C
• InChI: InChI=1S/C35H56O8/c1-21(2)11-10-14-34(9,40)35(41)18-17-33(8)29(35)23(42-22(3)36)19-25-31(6)15-13-26(43-28(39)20-27(37)38)30(4,5)24(31)12-16-32(25,33)7/h11,23-26,29,40-41H,10,12-20H2,1-9H3,(H,37,38)/t23-,24+,25-,26-,29+,31+,32-,33-,34+,35-/m1/s1
• InChI Key: ZJQWQSQAAISKMX-GZKZZVJFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₆O₈
• Molecular Weight: 604.80 g/mol
• Exact Mass: 604.39751874 g/mol
• Topological Polar Surface Area (TPSA): 130.00 Ų
• XlogP: 6.80
• Atomic LogP (AlogP): 6.21
• H-Bond Acceptor: 7
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9827	98.27%
Caco-2	-	0.7869	78.69%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.8474	84.74%
OATP2B1 inhibitior	-	0.5643	56.43%
OATP1B1 inhibitior	+	0.8074	80.74%
OATP1B3 inhibitior	-	0.2902	29.02%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7282	72.82%
BSEP inhibitior	+	0.8846	88.46%
P-glycoprotein inhibitior	+	0.7726	77.26%
P-glycoprotein substrate	-	0.5695	56.95%
CYP3A4 substrate	+	0.7249	72.49%
CYP2C9 substrate	-	0.6153	61.53%
CYP2D6 substrate	-	0.8874	88.74%
CYP3A4 inhibition	-	0.7581	75.81%
CYP2C9 inhibition	-	0.7664	76.64%
CYP2C19 inhibition	-	0.7585	75.85%
CYP2D6 inhibition	-	0.9582	95.82%
CYP1A2 inhibition	-	0.8366	83.66%
CYP2C8 inhibition	+	0.6284	62.84%
CYP inhibitory promiscuity	-	0.9350	93.50%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6744	67.44%
Eye corrosion	-	0.9943	99.43%
Eye irritation	-	0.9151	91.51%
Skin irritation	+	0.6531	65.31%
Skin corrosion	-	0.9470	94.70%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6630	66.30%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.8193	81.93%
skin sensitisation	-	0.7934	79.34%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.7300	73.00%
Acute Oral Toxicity (c)	I	0.6570	65.70%
Estrogen receptor binding	+	0.6789	67.89%
Androgen receptor binding	+	0.6838	68.38%
Thyroid receptor binding	-	0.4913	49.13%
Glucocorticoid receptor binding	+	0.7191	71.91%
Aromatase binding	+	0.7783	77.83%
PPAR gamma	+	0.6626	66.26%
Honey bee toxicity	-	0.6608	66.08%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9970	99.70%

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	96.51%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.44%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.12%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.73%	94.45%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.37%	94.62%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.24%	97.25%
CHEMBL340	P08684	Cytochrome P450 3A4	89.10%	91.19%
CHEMBL2996	Q05655	Protein kinase C delta	88.37%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.10%	97.09%
CHEMBL5028	O14672	ADAM10	86.73%	97.50%
CHEMBL1914	P06276	Butyrylcholinesterase	86.70%	95.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.44%	95.89%
CHEMBL2581	P07339	Cathepsin D	86.27%	98.95%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	85.97%	90.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.62%	85.14%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.54%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	83.88%	96.90%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.87%	94.08%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.63%	97.28%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.58%	86.33%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	83.36%	94.23%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.20%	94.33%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.91%	89.50%
CHEMBL1974	P36888	Tyrosine-protein kinase receptor FLT3	82.11%	91.83%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.77%	82.50%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	81.53%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.17%	92.62%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.96%	95.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.88%	91.07%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.76%	82.69%

Plants that contains it

• Betula pendula

Cross-Links

• PubChem: 101647895
• LOTUS: LTS0105649
• wikiData: Q105378075