Methyl betulinate

Details

• Internal ID: 514bf15b-98a5-4275-be7e-3f86f817a5d5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: methyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-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
• SMILES (Canonical): CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)C)C)(C)C)O)C)C(=O)OC
• 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)C)C)(C)C)O)C)C(=O)OC
• InChI: InChI=1S/C31H50O3/c1-19(2)20-11-16-31(26(33)34-8)18-17-29(6)21(25(20)31)9-10-23-28(5)14-13-24(32)27(3,4)22(28)12-15-30(23,29)7/h20-25,32H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24-,25+,28-,29+,30+,31-/m0/s1
• InChI Key: XNZIMRUZBOZIBC-JVRMVBBZSA-N
• Popularity: 42 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₅₀O₃
• Molecular Weight: 470.70 g/mol
• Exact Mass: 470.37599545 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 8.50

Synonyms

• METHYL BETULINATE
• 2259-06-5
• betulinic acid methylester
• CHEMBL295602
• NSC152532
• methyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-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
• (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-methyl 9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylate
• betulinate, Methyl
• Methyl 3-hydroxylup-20(29)-en-28-oate
• 28-O-Methylbetulinic Acid
• SCHEMBL2421615
• Lup-20(29)-en-28-oic acid, 3-hydroxy-, methyl ester, (3.beta.)-
• CHEBI:184030
• HY-N6587
• EINECS 218-857-6
• BDBM50240501
• MFCD00017379
• NSC 152532
• CS-0034288
• Methyl 3beta-Hydroxylup-20(29)-en-28-oate
• (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR)-methyl 9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxylate
• (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-Hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-icosahydro-cyclopenta[a]chrysene-3a-carboxylic acid methyl ester
• methyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2047	Q96RI1	Bile acid receptor FXR	0 nM	EC50	PMID: 19911773

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	98.75%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.52%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.73%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	92.12%	91.19%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	90.82%	96.38%
CHEMBL204	P00734	Thrombin	90.52%	96.01%
CHEMBL233	P35372	Mu opioid receptor	88.23%	97.93%
CHEMBL2581	P07339	Cathepsin D	87.98%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	87.81%	91.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.73%	92.94%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.10%	94.33%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.49%	91.24%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	84.79%	92.86%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.67%	82.69%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.66%	96.95%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	84.07%	93.03%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.01%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.71%	96.77%
CHEMBL1907601	P11802	Cyclin-dependent kinase 4/cyclin D1	83.68%	98.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.22%	95.89%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	82.37%	99.17%
CHEMBL5028	O14672	ADAM10	82.30%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.70%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.83%	100.00%
CHEMBL1974	P36888	Tyrosine-protein kinase receptor FLT3	80.69%	91.83%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.68%	95.50%

Plants that contains it

• Abutilon indicum
• Angylocalyx oligophyllus
• Baccharis minutiflora
• Cyclolepis genistoides
• Eriobotrya japonica
• Eucalyptus globulus
• Euptelea polyandra
• Hedera rhombea
• Hypericum perforatum
• Ixeridium gracile
• Morus macroura
• Prunella vulgaris
• Tricalysia okelensis

Cross-Links

• PubChem: 73493
• NPASS: NPC12774
• ChEMBL: CHEMBL295602
• LOTUS: LTS0257735
• wikiData: Q105337617