(1S,3S,4S,6S,7S,8R,11S,12S,15R,16R)-4,6-diacetyloxy-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: 6de3eeb7-6402-41d8-8e18-ea05b8b48a22
• 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)-4,6-diacetyloxy-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)OC(=O)C)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)OC(=O)C)OC(=O)C)C)C
• InChI: InChI=1S/C35H54O6/c1-20(2)21(3)10-11-22(4)25-14-15-32(8)26-12-13-27-33(9,30(38)39)28(40-23(5)36)18-29(41-24(6)37)35(27)19-34(26,35)17-16-31(25,32)7/h20,22,25-29H,3,10-19H2,1-2,4-9H3,(H,38,39)/t22-,25-,26+,27+,28+,29+,31-,32+,33+,34+,35-/m1/s1
• InChI Key: XXQZXARMTRVCHW-VSMYQFNNSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₄O₆
• Molecular Weight: 570.80 g/mol
• Exact Mass: 570.39203944 g/mol
• Topological Polar Surface Area (TPSA): 89.90 Ų
• XlogP: 9.00
• Atomic LogP (AlogP): 7.59
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 8

Synonyms

• 1alpha,3beta-Diacetoxy-24-methylenecycloartane-28-oic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9841	98.41%
Caco-2	-	0.7801	78.01%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7570	75.70%
OATP2B1 inhibitior	-	0.5666	56.66%
OATP1B1 inhibitior	+	0.8489	84.89%
OATP1B3 inhibitior	-	0.3526	35.26%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8527	85.27%
P-glycoprotein inhibitior	+	0.7289	72.89%
P-glycoprotein substrate	-	0.5501	55.01%
CYP3A4 substrate	+	0.6923	69.23%
CYP2C9 substrate	-	0.5969	59.69%
CYP2D6 substrate	-	0.8736	87.36%
CYP3A4 inhibition	-	0.7829	78.29%
CYP2C9 inhibition	-	0.6912	69.12%
CYP2C19 inhibition	-	0.8211	82.11%
CYP2D6 inhibition	-	0.9561	95.61%
CYP1A2 inhibition	-	0.6472	64.72%
CYP2C8 inhibition	+	0.5656	56.56%
CYP inhibitory promiscuity	-	0.8436	84.36%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6647	66.47%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9021	90.21%
Skin irritation	+	0.5709	57.09%
Skin corrosion	-	0.9462	94.62%
Ames mutagenesis	-	0.6228	62.28%
Human Ether-a-go-go-Related Gene inhibition	-	0.5666	56.66%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.6088	60.88%
skin sensitisation	-	0.7217	72.17%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.4621	46.21%
Acute Oral Toxicity (c)	I	0.4452	44.52%
Estrogen receptor binding	+	0.7589	75.89%
Androgen receptor binding	+	0.7348	73.48%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7350	73.50%
Aromatase binding	+	0.7421	74.21%
PPAR gamma	+	0.6847	68.47%
Honey bee toxicity	-	0.7027	70.27%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5755	57.55%
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
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.33%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.94%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	97.76%	95.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.99%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.62%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	95.10%	91.19%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	90.36%	93.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.48%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.12%	97.09%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	86.51%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.15%	96.61%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.47%	96.77%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.28%	89.05%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.21%	94.62%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.88%	96.95%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.54%	96.47%
CHEMBL3837	P07711	Cathepsin L	83.70%	96.61%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.12%	93.04%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.79%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.76%	95.89%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	81.92%	82.69%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.61%	82.50%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	81.56%	95.71%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.48%	89.50%
CHEMBL2581	P07339	Cathepsin D	81.15%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.12%	95.50%
CHEMBL4683	Q12884	Fibroblast activation protein alpha	80.86%	93.07%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.14%	98.75%

Plants that contains it

• Combretum quadrangulare

Cross-Links

• PubChem: 10769395
• NPASS: NPC472028
• ChEMBL: CHEMBL333068
• LOTUS: LTS0202634
• wikiData: Q105344172