(1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-4-acetyloxy-6-hydroxy-7,12,16-trimethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylic acid

Details

• Internal ID: f52a0822-d3b4-4bb9-8196-454ba6ca189a
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Cycloartanols and derivatives
• IUPAC Name: (1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-4-acetyloxy-6-hydroxy-7,12,16-trimethyl-15-[(2R)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylic acid
• SMILES (Canonical): CC(C)C(=C)CCC(C)C1CCC2(C1(CCC34C2CCC5C3(C4)C(CC(C5(C)C(=O)O)O)OC(=O)C)C)C
• SMILES (Isomeric): C[C@H](CCC(=C)C(C)C)[C@H]1CC[C@@]2([C@@]1(CC[C@]34[C@H]2CC[C@@H]5[C@]3(C4)[C@H](C[C@@H]([C@@]5(C)C(=O)O)O)OC(=O)C)C)C
• InChI: InChI=1S/C33H52O5/c1-19(2)20(3)9-10-21(4)23-13-14-30(7)24-11-12-25-31(8,28(36)37)26(35)17-27(38-22(5)34)33(25)18-32(24,33)16-15-29(23,30)6/h19,21,23-27,35H,3,9-18H2,1-2,4-8H3,(H,36,37)/t21-,23-,24+,25+,26+,27+,29-,30+,31+,32+,33-/m1/s1
• InChI Key: ZQZWWIJULHBFKT-MMTPFLLOSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₂O₅
• Molecular Weight: 528.80 g/mol
• Exact Mass: 528.38147475 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: 9.00
• Atomic LogP (AlogP): 7.02
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• 1-O-Acetyl-23-deoxojessic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9719	97.19%
Caco-2	-	0.6927	69.27%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6496	64.96%
OATP2B1 inhibitior	-	0.5680	56.80%
OATP1B1 inhibitior	+	0.8510	85.10%
OATP1B3 inhibitior	-	0.2243	22.43%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6505	65.05%
P-glycoprotein inhibitior	+	0.6028	60.28%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.7040	70.40%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8591	85.91%
CYP3A4 inhibition	-	0.6948	69.48%
CYP2C9 inhibition	-	0.6232	62.32%
CYP2C19 inhibition	-	0.8449	84.49%
CYP2D6 inhibition	-	0.9437	94.37%
CYP1A2 inhibition	-	0.8121	81.21%
CYP2C8 inhibition	+	0.5528	55.28%
CYP inhibitory promiscuity	-	0.8098	80.98%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6973	69.73%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.9149	91.49%
Skin irritation	+	0.5622	56.22%
Skin corrosion	-	0.9393	93.93%
Ames mutagenesis	-	0.6465	64.65%
Human Ether-a-go-go-Related Gene inhibition	-	0.5359	53.59%
Micronuclear	-	0.6600	66.00%
Hepatotoxicity	-	0.6267	62.67%
skin sensitisation	-	0.7480	74.80%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.6922	69.22%
Acute Oral Toxicity (c)	I	0.6997	69.97%
Estrogen receptor binding	+	0.7405	74.05%
Androgen receptor binding	+	0.7390	73.90%
Thyroid receptor binding	+	0.5605	56.05%
Glucocorticoid receptor binding	+	0.7051	70.51%
Aromatase binding	+	0.7275	72.75%
PPAR gamma	+	0.6632	66.32%
Honey bee toxicity	-	0.7092	70.92%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5955	59.55%
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	98.11%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.64%	97.25%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	96.24%	95.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.80%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.67%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	93.44%	91.19%
CHEMBL2179	P04062	Beta-glucocerebrosidase	90.51%	85.31%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	90.20%	96.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.70%	93.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.48%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.80%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	85.67%	96.61%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.54%	96.47%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.12%	96.77%
CHEMBL3837	P07711	Cathepsin L	85.11%	96.61%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.40%	95.89%
CHEMBL2581	P07339	Cathepsin D	83.81%	98.95%
CHEMBL4683	Q12884	Fibroblast activation protein alpha	83.79%	93.07%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	83.37%	82.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.79%	100.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.56%	94.62%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.42%	93.04%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.41%	89.05%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.38%	95.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.36%	98.75%
CHEMBL2815	P04629	Nerve growth factor receptor Trk-A	81.60%	87.16%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.40%	95.71%
CHEMBL274	P51681	C-C chemokine receptor type 5	80.77%	98.77%
CHEMBL221	P23219	Cyclooxygenase-1	80.34%	90.17%
CHEMBL237	P41145	Kappa opioid receptor	80.30%	98.10%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.09%	89.50%
CHEMBL5028	O14672	ADAM10	80.00%	97.50%

Plants that contains it

• Combretum quadrangulare

Cross-Links

• PubChem: 10816013
• NPASS: NPC94906
• ChEMBL: CHEMBL118366
• LOTUS: LTS0076288
• wikiData: Q105381837