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

Details

• Internal ID: a3f8ee81-6ea0-4e91-b83b-b63a727bfb9d
• 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-hydroxy-7,12,16-trimethyl-15-[(2R)-6-methyl-5-oxohept-6-en-2-yl]-6-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxypentacyclo[9.7.0.01,3.03,8.012,16]octadecane-7-carboxylic acid
• SMILES (Canonical): CC(CCC(=O)C(=C)C)C1CCC2(C1(CCC34C2CCC5C3(C4)C(CC(C5(C)C(=O)O)OC6C(C(C(CO6)O)O)O)O)C)C
• SMILES (Isomeric): C[C@H](CCC(=O)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[C@H]6[C@@H]([C@H]([C@@H](CO6)O)O)O)O)C)C
• InChI: InChI=1S/C35H54O9/c1-18(2)21(36)8-7-19(3)20-11-12-32(5)23-9-10-24-33(6,30(41)42)26(44-29-28(40)27(39)22(37)16-43-29)15-25(38)35(24)17-34(23,35)14-13-31(20,32)4/h19-20,22-29,37-40H,1,7-17H2,2-6H3,(H,41,42)/t19-,20-,22-,23+,24+,25+,26+,27+,28-,29+,31-,32+,33+,34+,35-/m1/s1
• InChI Key: ACPHWWDOVMFRGJ-QAAQEUGCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₄O₉
• Molecular Weight: 618.80 g/mol
• Exact Mass: 618.37678330 g/mol
• Topological Polar Surface Area (TPSA): 154.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 3.85
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8353	83.53%
Caco-2	-	0.8587	85.87%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7374	73.74%
OATP2B1 inhibitior	-	0.5749	57.49%
OATP1B1 inhibitior	+	0.8451	84.51%
OATP1B3 inhibitior	+	0.9460	94.60%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7622	76.22%
BSEP inhibitior	-	0.6895	68.95%
P-glycoprotein inhibitior	+	0.7054	70.54%
P-glycoprotein substrate	+	0.6050	60.50%
CYP3A4 substrate	+	0.7214	72.14%
CYP2C9 substrate	-	0.8000	80.00%
CYP2D6 substrate	-	0.8860	88.60%
CYP3A4 inhibition	-	0.7844	78.44%
CYP2C9 inhibition	-	0.6908	69.08%
CYP2C19 inhibition	-	0.8344	83.44%
CYP2D6 inhibition	-	0.9430	94.30%
CYP1A2 inhibition	-	0.8109	81.09%
CYP2C8 inhibition	+	0.6281	62.81%
CYP inhibitory promiscuity	-	0.9324	93.24%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7360	73.60%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9267	92.67%
Skin irritation	+	0.5319	53.19%
Skin corrosion	-	0.9355	93.55%
Ames mutagenesis	-	0.5937	59.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7048	70.48%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.6613	66.13%
skin sensitisation	-	0.8923	89.23%
Respiratory toxicity	+	0.5778	57.78%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.8500	85.00%
Nephrotoxicity	-	0.8021	80.21%
Acute Oral Toxicity (c)	I	0.4218	42.18%
Estrogen receptor binding	+	0.6680	66.80%
Androgen receptor binding	+	0.7489	74.89%
Thyroid receptor binding	-	0.5937	59.37%
Glucocorticoid receptor binding	+	0.6313	63.13%
Aromatase binding	+	0.6812	68.12%
PPAR gamma	+	0.6308	63.08%
Honey bee toxicity	-	0.6808	68.08%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6655	66.55%
Fish aquatic toxicity	+	0.9905	99.05%

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	98.36%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.64%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.36%	91.11%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.96%	95.17%
CHEMBL218	P21554	Cannabinoid CB1 receptor	91.80%	96.61%
CHEMBL340	P08684	Cytochrome P450 3A4	91.40%	91.19%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	91.18%	91.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.55%	94.45%
CHEMBL4040	P28482	MAP kinase ERK2	89.69%	83.82%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.30%	96.38%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.78%	97.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.13%	90.71%
CHEMBL2581	P07339	Cathepsin D	86.96%	98.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	86.31%	93.00%
CHEMBL2179	P04062	Beta-glucocerebrosidase	86.12%	85.31%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.64%	89.50%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.45%	92.62%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	85.31%	95.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.17%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.92%	95.89%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	84.79%	82.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.78%	100.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	83.70%	96.47%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	83.59%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	82.70%	96.77%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	82.69%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.58%	95.89%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.28%	95.71%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.21%	96.95%
CHEMBL3359	P21462	Formyl peptide receptor 1	81.83%	93.56%
CHEMBL1075317	P61964	WD repeat-containing protein 5	81.65%	96.33%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.53%	95.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.93%	89.00%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	80.86%	89.05%

Plants that contains it

• Markhamia lutea

Cross-Links

• PubChem: 162971036
• LOTUS: LTS0215577
• wikiData: Q104909221