Methyl 3alpha-acetoxy-27-hydroxylup-20(29)-en-24-oate

Details

• Internal ID: 0bf670cb-7496-4f62-b95f-6c418c06d762
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: methyl (1R,3aR,5aS,5bR,7aR,8R,9R,11aR,11bR,13aR,13bR)-9-acetyloxy-5a-(hydroxymethyl)-3a,5b,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-8-carboxylate
• SMILES (Canonical): CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)CO)C)(C)C(=O)OC)OC(=O)C)C)C
• SMILES (Isomeric): CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@H]([C@]([C@@H]5CC[C@]4([C@@]3(CC2)CO)C)(C)C(=O)OC)OC(=O)C)C)C
• InChI: InChI=1S/C33H52O5/c1-20(2)22-11-14-29(4)17-18-33(19-34)23(27(22)29)9-10-24-30(5)15-13-26(38-21(3)35)32(7,28(36)37-8)25(30)12-16-31(24,33)6/h22-27,34H,1,9-19H2,2-8H3/t22-,23+,24+,25+,26+,27+,29+,30+,31+,32+,33-/m0/s1
• InChI Key: OZFWHMKAQGWDTK-RPSYARDLSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₂O₅
• Molecular Weight: 528.80 g/mol
• Exact Mass: 528.38147475 g/mol
• Topological Polar Surface Area (TPSA): 72.80 Ų
• XlogP: 8.10
• Atomic LogP (AlogP): 6.72
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

• BDBM50259883
• methyl 3alpha-acetoxy-27-hydroxylup-20(29)-en-24-oate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9854	98.54%
Caco-2	-	0.7084	70.84%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8380	83.80%
OATP2B1 inhibitior	-	0.7073	70.73%
OATP1B1 inhibitior	+	0.8650	86.50%
OATP1B3 inhibitior	+	0.8277	82.77%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.5168	51.68%
BSEP inhibitior	+	0.7934	79.34%
P-glycoprotein inhibitior	+	0.5753	57.53%
P-glycoprotein substrate	-	0.6073	60.73%
CYP3A4 substrate	+	0.7155	71.55%
CYP2C9 substrate	-	0.8092	80.92%
CYP2D6 substrate	-	0.8657	86.57%
CYP3A4 inhibition	-	0.7257	72.57%
CYP2C9 inhibition	-	0.8026	80.26%
CYP2C19 inhibition	-	0.8575	85.75%
CYP2D6 inhibition	-	0.9607	96.07%
CYP1A2 inhibition	-	0.7453	74.53%
CYP2C8 inhibition	+	0.6071	60.71%
CYP inhibitory promiscuity	-	0.8814	88.14%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9720	97.20%
Carcinogenicity (trinary)	Non-required	0.6859	68.59%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9052	90.52%
Skin irritation	+	0.4929	49.29%
Skin corrosion	-	0.9647	96.47%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3885	38.85%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.7129	71.29%
skin sensitisation	-	0.9202	92.02%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.5793	57.93%
Acute Oral Toxicity (c)	III	0.5753	57.53%
Estrogen receptor binding	+	0.6954	69.54%
Androgen receptor binding	+	0.7619	76.19%
Thyroid receptor binding	-	0.5053	50.53%
Glucocorticoid receptor binding	+	0.7410	74.10%
Aromatase binding	+	0.7262	72.62%
PPAR gamma	+	0.6423	64.23%
Honey bee toxicity	-	0.6674	66.74%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.35%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.09%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.56%	97.25%
CHEMBL233	P35372	Mu opioid receptor	92.50%	97.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	92.30%	96.61%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.54%	96.38%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.28%	85.14%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	89.81%	95.36%
CHEMBL4482	O96013	Serine/threonine-protein kinase PAK 4	88.90%	95.42%
CHEMBL2581	P07339	Cathepsin D	88.66%	98.95%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	88.20%	82.69%
CHEMBL340	P08684	Cytochrome P450 3A4	87.64%	91.19%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.57%	92.62%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.65%	96.95%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	85.60%	97.50%
CHEMBL204	P00734	Thrombin	85.58%	96.01%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.70%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.36%	95.89%
CHEMBL237	P41145	Kappa opioid receptor	84.22%	98.10%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.08%	91.24%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.98%	91.03%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.90%	94.33%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	83.72%	98.99%
CHEMBL5028	O14672	ADAM10	83.63%	97.50%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.55%	91.11%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.28%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.39%	95.50%
CHEMBL2094128	P24941	Cyclin-dependent kinase 2/cyclin A	81.79%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.52%	97.09%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.43%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.27%	97.14%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.23%	96.77%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.12%	97.29%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.83%	93.04%

Plants that contains it

• Boswellia papyrifera

Cross-Links

• PubChem: 44575408
• LOTUS: LTS0184491
• wikiData: Q105203766