Methyl betulate

Details

• Internal ID: f24ba421-a0b8-4a61-9f70-511e4acc5812
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: methyl 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)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(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
• InChI Key: XNZIMRUZBOZIBC-UHFFFAOYSA-N
• Popularity: 0 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
• Atomic LogP (AlogP): 7.18
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• methyl 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
• Lup-20(29)-en-28-oic acid, 3-hydroxy-, methyl ester, (3beta)-
• Methyl 3-hydroxylup-20(29)-en-28-oate
• Lup-20(29)-en-28-oic acid, 3-hydroxy-, methyl ester, (3.beta.)-
• DTXSID90945239
• XNZIMRUZBOZIBC-UHFFFAOYSA-N
• NSC-152532
• FT-0771363
• Lup-20(29)-en-28-oic acid, methyl ester
• Methyl 3-hydroxylup-20(29)-en-28-oate #
• Lup-20(29)-en-28-oic acid, methyl ester, (3.beta.)-
• Lup-20(29)-en-28-oic acid, 3.beta.-hydroxy-, methyl ester

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9961	99.61%
Caco-2	-	0.5650	56.50%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8268	82.68%
OATP2B1 inhibitior	-	0.7144	71.44%
OATP1B1 inhibitior	+	0.9235	92.35%
OATP1B3 inhibitior	-	0.3931	39.31%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5500	55.00%
BSEP inhibitior	+	0.6521	65.21%
P-glycoprotein inhibitior	-	0.7547	75.47%
P-glycoprotein substrate	-	0.7402	74.02%
CYP3A4 substrate	+	0.7058	70.58%
CYP2C9 substrate	-	0.6346	63.46%
CYP2D6 substrate	-	0.7958	79.58%
CYP3A4 inhibition	-	0.7385	73.85%
CYP2C9 inhibition	-	0.6361	63.61%
CYP2C19 inhibition	-	0.6973	69.73%
CYP2D6 inhibition	-	0.9512	95.12%
CYP1A2 inhibition	-	0.8296	82.96%
CYP2C8 inhibition	+	0.4834	48.34%
CYP inhibitory promiscuity	-	0.8943	89.43%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5883	58.83%
Eye corrosion	-	0.9934	99.34%
Eye irritation	-	0.9057	90.57%
Skin irritation	+	0.5944	59.44%
Skin corrosion	-	0.9619	96.19%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4575	45.75%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.8698	86.98%
skin sensitisation	-	0.6247	62.47%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.8875	88.75%
Nephrotoxicity	-	0.7847	78.47%
Acute Oral Toxicity (c)	III	0.5708	57.08%
Estrogen receptor binding	+	0.7473	74.73%
Androgen receptor binding	+	0.7807	78.07%
Thyroid receptor binding	+	0.6059	60.59%
Glucocorticoid receptor binding	+	0.7998	79.98%
Aromatase binding	+	0.7065	70.65%
PPAR gamma	+	0.5697	56.97%
Honey bee toxicity	-	0.5887	58.87%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9959	99.59%

Targets

Proven Targets:

No proven targets yet!

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

• Baccharis minutiflora
• Cantinoa mutabilis
• Cyclolepis genistoides
• Eriobotrya japonica
• Eucalyptus globulus
• Frangula granulosa
• Ixeridium gracile
• Prunella vulgaris
• Rhodomyrtus tomentosa
• Syzygium samarangense

Cross-Links

• PubChem: 423298
• NPASS: NPC311666
• LOTUS: LTS0015878
• wikiData: Q82922511