3-[[(3R,5R,8R,9R,10R,12R,13R,14R,17R)-12-acetyloxy-17-[(E,2S)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-17-hydroxy-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: f1920707-b21b-4729-9178-595afa187aa6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: 3-[[(3R,5R,8R,9R,10R,12R,13R,14R,17R)-12-acetyloxy-17-[(E,2S)-2,6-dihydroxy-6-methylhept-4-en-2-yl]-17-hydroxy-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(=O)OC1CC2C3(CCC(C(C3CCC2(C4(C1C(CC4)(C(C)(CC=CC(C)(C)O)O)O)C)C)(C)C)OC(=O)CC(=O)O)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@]3(CC[C@H](C([C@@H]3CC[C@]2([C@]4([C@H]1[C@](CC4)([C@](C)(C/C=C/C(C)(C)O)O)O)C)C)(C)C)OC(=O)CC(=O)O)C
• InChI: InChI=1S/C35H56O9/c1-21(36)43-22-19-24-31(6)15-12-25(44-27(39)20-26(37)38)30(4,5)23(31)11-16-32(24,7)33(8)17-18-35(42,28(22)33)34(9,41)14-10-13-29(2,3)40/h10,13,22-25,28,40-42H,11-12,14-20H2,1-9H3,(H,37,38)/b13-10+/t22-,23+,24-,25-,28+,31+,32-,33-,34+,35-/m1/s1
• InChI Key: OITYFEGPXGMPAP-JNNIKVRZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₆O₉
• Molecular Weight: 620.80 g/mol
• Exact Mass: 620.39243336 g/mol
• Topological Polar Surface Area (TPSA): 151.00 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.18
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9749	97.49%
Caco-2	-	0.8040	80.40%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8389	83.89%
OATP2B1 inhibitior	-	0.5712	57.12%
OATP1B1 inhibitior	+	0.8303	83.03%
OATP1B3 inhibitior	-	0.2312	23.12%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.8903	89.03%
P-glycoprotein inhibitior	+	0.7783	77.83%
P-glycoprotein substrate	-	0.5180	51.80%
CYP3A4 substrate	+	0.7356	73.56%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8889	88.89%
CYP3A4 inhibition	-	0.7095	70.95%
CYP2C9 inhibition	-	0.8699	86.99%
CYP2C19 inhibition	-	0.7474	74.74%
CYP2D6 inhibition	-	0.9724	97.24%
CYP1A2 inhibition	-	0.8186	81.86%
CYP2C8 inhibition	+	0.6470	64.70%
CYP inhibitory promiscuity	-	0.9649	96.49%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7002	70.02%
Eye corrosion	-	0.9938	99.38%
Eye irritation	-	0.9155	91.55%
Skin irritation	+	0.6154	61.54%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3704	37.04%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.7959	79.59%
skin sensitisation	-	0.8477	84.77%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.9750	97.50%
Nephrotoxicity	-	0.7249	72.49%
Acute Oral Toxicity (c)	I	0.5956	59.56%
Estrogen receptor binding	+	0.6948	69.48%
Androgen receptor binding	+	0.6758	67.58%
Thyroid receptor binding	+	0.5399	53.99%
Glucocorticoid receptor binding	+	0.6894	68.94%
Aromatase binding	+	0.7460	74.60%
PPAR gamma	+	0.6608	66.08%
Honey bee toxicity	-	0.6893	68.93%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9960	99.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.46%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.84%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	93.83%	97.25%
CHEMBL1914	P06276	Butyrylcholinesterase	90.83%	95.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.63%	94.62%
CHEMBL2996	Q05655	Protein kinase C delta	89.08%	97.79%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.55%	82.69%
CHEMBL340	P08684	Cytochrome P450 3A4	88.31%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.54%	91.07%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.37%	85.14%
CHEMBL203	P00533	Epidermal growth factor receptor erbB1	85.81%	97.34%
CHEMBL5028	O14672	ADAM10	85.75%	97.50%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	85.60%	90.93%
CHEMBL2413	P32246	C-C chemokine receptor type 1	84.84%	89.50%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.80%	97.28%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	84.77%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.63%	100.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	83.34%	94.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.30%	94.45%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.14%	94.33%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	82.82%	82.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.40%	97.09%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	82.37%	91.03%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	82.17%	94.23%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.13%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.64%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.49%	92.62%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.42%	93.00%

Plants that contains it

• Betula pendula

Cross-Links

• PubChem: 102586238
• LOTUS: LTS0233568
• wikiData: Q105192753