3Alpha-Acetoxy-27-Hydroxylup-20(29)-En-24-Oic Acid

Details

• Internal ID: 26d4cabe-0ccd-4c7b-aa34-323e0b6e33f3
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (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-carboxylic acid
• SMILES (Canonical): CC(=C)C1CCC2(C1C3CCC4C5(CCC(C(C5CCC4(C3(CC2)CO)C)(C)C(=O)O)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)O)OC(=O)C)C)C
• InChI: InChI=1S/C32H50O5/c1-19(2)21-10-13-28(4)16-17-32(18-33)22(26(21)28)8-9-23-29(5)14-12-25(37-20(3)34)31(7,27(35)36)24(29)11-15-30(23,32)6/h21-26,33H,1,8-18H2,2-7H3,(H,35,36)/t21-,22+,23+,24+,25+,26+,28+,29+,30+,31+,32-/m0/s1
• InChI Key: SFMBHTKBXIQXHJ-LBIUZANVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₅₀O₅
• Molecular Weight: 514.70 g/mol
• Exact Mass: 514.36582469 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 7.70
• Atomic LogP (AlogP): 6.63
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• (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-carboxylic acid
• (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-carboxylic acid
• RefChem:95580
• 847844-98-8
• CHEMBL499293
• BDBM50259880

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9826	98.26%
Caco-2	-	0.7263	72.63%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8475	84.75%
OATP2B1 inhibitior	-	0.5658	56.58%
OATP1B1 inhibitior	+	0.8586	85.86%
OATP1B3 inhibitior	+	0.8227	82.27%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6037	60.37%
BSEP inhibitior	+	0.7512	75.12%
P-glycoprotein inhibitior	-	0.5429	54.29%
P-glycoprotein substrate	-	0.7009	70.09%
CYP3A4 substrate	+	0.6970	69.70%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8819	88.19%
CYP3A4 inhibition	-	0.7102	71.02%
CYP2C9 inhibition	-	0.8595	85.95%
CYP2C19 inhibition	-	0.9209	92.09%
CYP2D6 inhibition	-	0.9524	95.24%
CYP1A2 inhibition	-	0.8061	80.61%
CYP2C8 inhibition	+	0.6033	60.33%
CYP inhibitory promiscuity	-	0.8463	84.63%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6693	66.93%
Eye corrosion	-	0.9927	99.27%
Eye irritation	-	0.9123	91.23%
Skin irritation	+	0.5776	57.76%
Skin corrosion	-	0.9634	96.34%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4737	47.37%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.7346	73.46%
skin sensitisation	-	0.9244	92.44%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	+	0.4803	48.03%
Acute Oral Toxicity (c)	III	0.5815	58.15%
Estrogen receptor binding	+	0.6742	67.42%
Androgen receptor binding	+	0.7597	75.97%
Thyroid receptor binding	-	0.5226	52.26%
Glucocorticoid receptor binding	+	0.7419	74.19%
Aromatase binding	+	0.7350	73.50%
PPAR gamma	+	0.6222	62.22%
Honey bee toxicity	-	0.7293	72.93%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL3202	P48147	Prolyl endopeptidase	2866 nM	IC50	PMID: 8691203

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.07%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.34%	94.45%
CHEMBL233	P35372	Mu opioid receptor	93.09%	97.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.56%	97.25%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.83%	96.61%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	90.24%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	90.13%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	88.95%	90.17%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	86.80%	95.36%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	86.48%	96.38%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	85.46%	96.95%
CHEMBL2581	P07339	Cathepsin D	85.35%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.99%	92.62%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.83%	92.94%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.58%	93.04%
CHEMBL4482	O96013	Serine/threonine-protein kinase PAK 4	84.48%	95.42%
CHEMBL237	P41145	Kappa opioid receptor	84.18%	98.10%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.50%	93.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	83.26%	100.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.66%	97.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	82.65%	82.69%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.60%	95.89%
CHEMBL5028	O14672	ADAM10	81.89%	97.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.75%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.82%	86.33%
CHEMBL204	P00734	Thrombin	80.05%	96.01%

Plants that contains it

• Boswellia papyrifera

Cross-Links

• PubChem: 21575462
• NPASS: NPC287118
• ChEMBL: CHEMBL499293
• LOTUS: LTS0067784
• wikiData: Q104888468