(2S,4S,7R,8S,9S,12R,13R,16R,17S,18R)-16-acetyloxy-2,9,13,17-tetramethyl-7-(4-methyl-2-oxopent-3-enyl)-6-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-1(20)-ene-17-carboxylic acid

Details

• Internal ID: 3d15f035-8423-400c-b6cc-7e830cb2e2b5
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,4S,7R,8S,9S,12R,13R,16R,17S,18R)-16-acetyloxy-2,9,13,17-tetramethyl-7-(4-methyl-2-oxopent-3-enyl)-6-oxo-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-1(20)-ene-17-carboxylic acid
• SMILES (Canonical): CC(=CC(=O)CC1C2C(CC3(C2(CCC4C3=CCC5C4(CCC(C5(C)C(=O)O)OC(=O)C)C)C)C)OC1=O)C
• SMILES (Isomeric): CC(=CC(=O)C[C@@H]1[C@@H]2[C@H](C[C@]3([C@]2(CC[C@H]4C3=CC[C@@H]5[C@@]4(CC[C@H]([C@@]5(C)C(=O)O)OC(=O)C)C)C)C)OC1=O)C
• InChI: InChI=1S/C32H44O7/c1-17(2)14-19(34)15-20-26-23(39-27(20)35)16-31(6)22-8-9-24-29(4,21(22)10-13-30(26,31)5)12-11-25(38-18(3)33)32(24,7)28(36)37/h8,14,20-21,23-26H,9-13,15-16H2,1-7H3,(H,36,37)/t20-,21+,23+,24-,25-,26-,29-,30+,31-,32+/m1/s1
• InChI Key: FILHRDIXAYLUHH-XTURJDPMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₄O₇
• Molecular Weight: 540.70 g/mol
• Exact Mass: 540.30870374 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.66
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• BDBM50269526
• (1S,2R,4aR,4bR,6aS,6bS,7R,9aS,10aS,12aR)-2-Acetoxy-1,4a,6a,10a-tetramethyl-7-(4-methyl-2-oxo-pent-3-enyl)-8-oxo-2,3,4,4a,4b,5,6,6a,6b,7,8,9a,10,10a,12,12a-hexadecahydro-1H-9-oxa-pentaleno[2,1-a]phenanthrene-1-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9884	98.84%
Caco-2	-	0.7109	71.09%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7883	78.83%
OATP2B1 inhibitior	-	0.7212	72.12%
OATP1B1 inhibitior	+	0.7954	79.54%
OATP1B3 inhibitior	-	0.3793	37.93%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.9868	98.68%
P-glycoprotein inhibitior	+	0.8235	82.35%
P-glycoprotein substrate	-	0.5598	55.98%
CYP3A4 substrate	+	0.7013	70.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9145	91.45%
CYP3A4 inhibition	-	0.5352	53.52%
CYP2C9 inhibition	-	0.7602	76.02%
CYP2C19 inhibition	-	0.8478	84.78%
CYP2D6 inhibition	-	0.9459	94.59%
CYP1A2 inhibition	-	0.5129	51.29%
CYP2C8 inhibition	+	0.5977	59.77%
CYP inhibitory promiscuity	-	0.7681	76.81%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5663	56.63%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9204	92.04%
Skin irritation	+	0.6138	61.38%
Skin corrosion	-	0.9205	92.05%
Ames mutagenesis	-	0.6654	66.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6629	66.29%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	+	0.5750	57.50%
skin sensitisation	-	0.8087	80.87%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.6465	64.65%
Acute Oral Toxicity (c)	III	0.5425	54.25%
Estrogen receptor binding	+	0.7632	76.32%
Androgen receptor binding	+	0.7447	74.47%
Thyroid receptor binding	+	0.5876	58.76%
Glucocorticoid receptor binding	+	0.8340	83.40%
Aromatase binding	+	0.7874	78.74%
PPAR gamma	+	0.7035	70.35%
Honey bee toxicity	-	0.7906	79.06%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9970	99.70%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL204	P00734	Thrombin	18 nM; 18 nM	IC50; IC50	PMID: 23691952; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.97%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.40%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.75%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.61%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.25%	86.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.87%	93.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.38%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.88%	95.89%
CHEMBL3922	P50579	Methionine aminopeptidase 2	87.84%	97.28%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.23%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.10%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	84.50%	91.19%
CHEMBL2413	P32246	C-C chemokine receptor type 1	83.91%	89.50%
CHEMBL5028	O14672	ADAM10	82.81%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.39%	91.07%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.26%	99.23%

Plants that contains it

• Lantana camara

Cross-Links

• PubChem: 10674014
• NPASS: NPC220974
• ChEMBL: CHEMBL503000
• LOTUS: LTS0092586
• wikiData: Q104995761