3Alpha,27-Dihydroxylup-20(29)-En-28-Oic Acid Methyl Ester

Details

• Internal ID: b71bde04-acfc-49c4-9a33-1001f04113da
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: methyl (1R,3aS,5aS,5bR,7aR,9R,11aR,11bR,13aR,13bR)-9-hydroxy-5a-(hydroxymethyl)-5b,8,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
• InChI: InChI=1S/C31H50O4/c1-19(2)20-10-15-30(26(34)35-7)16-17-31(18-32)21(25(20)30)8-9-23-28(5)13-12-24(33)27(3,4)22(28)11-14-29(23,31)6/h20-25,32-33H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24+,25+,28-,29+,30-,31-/m0/s1
• InChI Key: UEBDDJDCLTYODS-VAPIBPPKSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₅₀O₄
• Molecular Weight: 486.70 g/mol
• Exact Mass: 486.37091007 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 7.10
• Atomic LogP (AlogP): 6.15
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• 3,27-Dihydroxy-20(29)-lupen-28-oic acid methyl ester
• CHEMBL525784
• methyl (1R,3aS,5aS,5bR,7aR,9R,11aR,11bR,13aR,13bR)-9-hydroxy-5a-(hydroxymethyl)-5b,8,8,11a-tetramethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
• 263844-79-7
• HY-N8676
• BDBM50269149
• AKOS040761055
• FS-9681
• CS-0148897
• 3alpha,27-dihydroxylup-20(29)-en-28-oic acid methyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9896	98.96%
Caco-2	-	0.5940	59.40%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8329	83.29%
OATP2B1 inhibitior	-	0.5742	57.42%
OATP1B1 inhibitior	+	0.8889	88.89%
OATP1B3 inhibitior	-	0.3226	32.26%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5885	58.85%
BSEP inhibitior	+	0.5514	55.14%
P-glycoprotein inhibitior	-	0.7780	77.80%
P-glycoprotein substrate	-	0.6646	66.46%
CYP3A4 substrate	+	0.7129	71.29%
CYP2C9 substrate	-	0.8066	80.66%
CYP2D6 substrate	-	0.8115	81.15%
CYP3A4 inhibition	-	0.7071	70.71%
CYP2C9 inhibition	-	0.7262	72.62%
CYP2C19 inhibition	-	0.9012	90.12%
CYP2D6 inhibition	-	0.9399	93.99%
CYP1A2 inhibition	-	0.8702	87.02%
CYP2C8 inhibition	+	0.5541	55.41%
CYP inhibitory promiscuity	-	0.8042	80.42%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7200	72.00%
Eye corrosion	-	0.9931	99.31%
Eye irritation	-	0.9226	92.26%
Skin irritation	-	0.5390	53.90%
Skin corrosion	-	0.9649	96.49%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5300	53.00%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7348	73.48%
skin sensitisation	-	0.8333	83.33%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.8124	81.24%
Acute Oral Toxicity (c)	III	0.6182	61.82%
Estrogen receptor binding	+	0.7001	70.01%
Androgen receptor binding	+	0.7879	78.79%
Thyroid receptor binding	+	0.5191	51.91%
Glucocorticoid receptor binding	+	0.7670	76.70%
Aromatase binding	+	0.6969	69.69%
PPAR gamma	+	0.5406	54.06%
Honey bee toxicity	-	0.6376	63.76%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9931	99.31%

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	97.52%	96.09%
CHEMBL204	P00734	Thrombin	93.66%	96.01%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.27%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.66%	91.11%
CHEMBL233	P35372	Mu opioid receptor	92.12%	97.93%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	91.38%	96.38%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.88%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	90.07%	91.19%
CHEMBL2581	P07339	Cathepsin D	88.87%	98.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.16%	94.33%
CHEMBL2996	Q05655	Protein kinase C delta	87.88%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.65%	97.09%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	87.10%	91.24%
CHEMBL4482	O96013	Serine/threonine-protein kinase PAK 4	87.01%	95.42%
CHEMBL4040	P28482	MAP kinase ERK2	86.27%	83.82%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.16%	95.50%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.58%	96.61%
CHEMBL226	P30542	Adenosine A1 receptor	84.43%	95.93%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.19%	96.77%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.89%	82.69%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.79%	95.89%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.16%	92.94%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.09%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.08%	95.89%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.56%	97.25%
CHEMBL5028	O14672	ADAM10	82.46%	97.50%
CHEMBL221	P23219	Cyclooxygenase-1	81.44%	90.17%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.31%	100.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	81.17%	92.86%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.71%	96.90%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	80.22%	87.16%
CHEMBL1871	P10275	Androgen Receptor	80.03%	96.43%

Plants that contains it

• Peganum nigellastrum

Cross-Links

• PubChem: 11799152
• LOTUS: LTS0111509
• wikiData: Q105270763