methyl (2R,4S,8R,9R,10Z,12R)-8-[(1aR,1bS,2R,6aS)-6-[(2R)-2-[(1aR,1bS,2R,6aS)-2-hydroxy-1b,6-dimethyl-3-oxo-1,1a,2,6a-tetrahydrocyclopropa[a]inden-4-yl]-3-methoxy-2-methyl-3-oxopropyl]-2-hydroxy-1b-methyl-3-oxo-1,1a,2,6a-tetrahydrocyclopropa[a]inden-4-yl]-12-hydroxy-10-(1-methoxy-1-oxopropan-2-ylidene)-11-oxotetracyclo[7.3.1.02,4.05,13]tridec-5(13)-ene-8-carboxylate

Details

• Internal ID: f75b1310-b3c0-4d26-9f0d-d15c3e772523
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: methyl (2R,4S,8R,9R,10Z,12R)-8-[(1aR,1bS,2R,6aS)-6-[(2R)-2-[(1aR,1bS,2R,6aS)-2-hydroxy-1b,6-dimethyl-3-oxo-1,1a,2,6a-tetrahydrocyclopropa[a]inden-4-yl]-3-methoxy-2-methyl-3-oxopropyl]-2-hydroxy-1b-methyl-3-oxo-1,1a,2,6a-tetrahydrocyclopropa[a]inden-4-yl]-12-hydroxy-10-(1-methoxy-1-oxopropan-2-ylidene)-11-oxotetracyclo[7.3.1.02,4.05,13]tridec-5(13)-ene-8-carboxylate
• SMILES (Canonical): CC1=C2C=C(C(=O)C(C2(C3C1C3)C)O)C(C)(CC4=C5C=C(C(=O)C(C5(C6C4C6)C)O)C7(CCC8=C9C7C(=C(C)C(=O)OC)C(=O)C(C9C1C8C1)O)C(=O)OC)C(=O)OC
• SMILES (Isomeric): CC1=C2C=C(C(=O)[C@@H]([C@]2([C@H]3[C@@H]1C3)C)O)[C@@](C)(CC4=C5C=C(C(=O)[C@@H]([C@]5([C@H]6[C@@H]4C6)C)O)[C@]7(CCC8=C9[C@@H]7/C(=C(\C)/C(=O)OC)/C(=O)[C@@H](C9[C@H]1[C@@H]8C1)O)C(=O)OC)C(=O)OC
• InChI: InChI=1S/C47H52O12/c1-17-20-12-26(20)45(4)25(17)14-29(35(48)39(45)52)44(3,42(55)58-7)16-24-22-13-27(22)46(5)28(24)15-30(36(49)40(46)53)47(43(56)59-8)10-9-19-21-11-23(21)33-32(19)34(47)31(37(50)38(33)51)18(2)41(54)57-6/h14-15,20-23,26-27,33-34,38-40,51-53H,9-13,16H2,1-8H3/b31-18-/t20-,21-,22-,23-,26-,27-,33?,34+,38-,39+,40+,44-,45-,46+,47+/m1/s1
• InChI Key: UQTZGEYXPZSUBF-NRUDQBQOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₅₂O₁₂
• Molecular Weight: 808.90 g/mol
• Exact Mass: 808.34587709 g/mol
• Topological Polar Surface Area (TPSA): 191.00 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 3.79
• H-Bond Acceptor: 12
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9858	98.58%
Caco-2	-	0.8459	84.59%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8289	82.89%
OATP2B1 inhibitior	-	0.8590	85.90%
OATP1B1 inhibitior	+	0.8137	81.37%
OATP1B3 inhibitior	+	0.8245	82.45%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9245	92.45%
P-glycoprotein inhibitior	+	0.7884	78.84%
P-glycoprotein substrate	+	0.7847	78.47%
CYP3A4 substrate	+	0.7446	74.46%
CYP2C9 substrate	-	0.7829	78.29%
CYP2D6 substrate	-	0.9026	90.26%
CYP3A4 inhibition	-	0.7619	76.19%
CYP2C9 inhibition	-	0.7348	73.48%
CYP2C19 inhibition	-	0.8579	85.79%
CYP2D6 inhibition	-	0.9119	91.19%
CYP1A2 inhibition	-	0.6484	64.84%
CYP2C8 inhibition	+	0.7507	75.07%
CYP inhibitory promiscuity	-	0.6792	67.92%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9720	97.20%
Carcinogenicity (trinary)	Non-required	0.6062	60.62%
Eye corrosion	-	0.9926	99.26%
Eye irritation	-	0.9099	90.99%
Skin irritation	+	0.5058	50.58%
Skin corrosion	-	0.9602	96.02%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4408	44.08%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.6179	61.79%
skin sensitisation	-	0.8242	82.42%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.8355	83.55%
Acute Oral Toxicity (c)	III	0.5117	51.17%
Estrogen receptor binding	+	0.8385	83.85%
Androgen receptor binding	+	0.7706	77.06%
Thyroid receptor binding	+	0.5338	53.38%
Glucocorticoid receptor binding	+	0.7947	79.47%
Aromatase binding	+	0.7005	70.05%
PPAR gamma	+	0.7805	78.05%
Honey bee toxicity	-	0.6036	60.36%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	98.80%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.29%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.59%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	95.97%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.38%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.31%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	94.04%	96.95%
CHEMBL340	P08684	Cytochrome P450 3A4	93.52%	91.19%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.71%	95.56%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	88.24%	96.90%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.64%	97.09%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	86.51%	90.93%
CHEMBL255	P29275	Adenosine A2b receptor	86.11%	98.59%
CHEMBL5028	O14672	ADAM10	85.46%	97.50%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.39%	97.21%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.87%	85.14%
CHEMBL2535	P11166	Glucose transporter	84.44%	98.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.44%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.24%	86.33%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.26%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.11%	89.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	82.52%	92.86%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.69%	99.23%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	80.98%	92.29%
CHEMBL1871	P10275	Androgen Receptor	80.01%	96.43%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 101938874
• LOTUS: LTS0154815
• wikiData: Q105277457