(2S,3S,4R,5R,6R)-7-[(3aS,5aR,5bR,7aS,11aS,11bR,13aR,13bS)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-[(2S,3S,4R,5S,6R)-3-(8-cyclohexyloctylamino)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctane-2,3,4,5,6-pentol

Details

• Internal ID: 1bf5dbd2-ce23-48cf-bbaa-e8fd24652296
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Hopanoids > Bacteriohopanoids
• IUPAC Name: (2S,3S,4R,5R,6R)-7-[(3aS,5aR,5bR,7aS,11aS,11bR,13aR,13bS)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]-1-[(2S,3S,4R,5S,6R)-3-(8-cyclohexyloctylamino)-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctane-2,3,4,5,6-pentol
• SMILES (Canonical): CC(C1CCC2(C1CCC3(C2CCC4C3(CCC5C4(CCCC5(C)C)C)C)C)C)C(C(C(C(C(COC6C(C(C(C(O6)CO)O)O)NCCCCCCCCC7CCCCC7)O)O)O)O)O
• SMILES (Isomeric): CC(C1CC[C@]2([C@H]1CC[C@@]3([C@@H]2CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CCCC5(C)C)C)C)C)C)[C@H]([C@H]([C@H]([C@H]([C@H](CO[C@@H]6[C@H]([C@H]([C@@H]([C@H](O6)CO)O)O)NCCCCCCCCC7CCCCC7)O)O)O)O)O
• InChI: InChI=1S/C55H99NO10/c1-34(36-23-28-52(4)37(36)24-29-54(6)41(52)21-22-42-53(5)27-17-26-51(2,3)40(53)25-30-55(42,54)7)44(59)48(63)49(64)45(60)38(58)33-65-50-43(47(62)46(61)39(32-57)66-50)56-31-16-11-9-8-10-13-18-35-19-14-12-15-20-35/h34-50,56-64H,8-33H2,1-7H3/t34?,36?,37-,38-,39+,40-,41+,42+,43-,44+,45-,46+,47+,48+,49-,50-,52-,53-,54+,55+/m0/s1
• InChI Key: YENKJXDSGUTSNU-AGAJEQGRSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₅H₉₉NO₁₀
• Molecular Weight: 934.40 g/mol
• Exact Mass: 933.72689835 g/mol
• Topological Polar Surface Area (TPSA): 192.00 Ų
• XlogP: 12.00
• Atomic LogP (AlogP): 7.64
• H-Bond Acceptor: 11
• H-Bond Donor: 9
• Rotatable Bonds: 20

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7219	72.19%
Caco-2	-	0.8686	86.86%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Lysosomes	0.4683	46.83%
OATP2B1 inhibitior	-	0.8639	86.39%
OATP1B1 inhibitior	+	0.8357	83.57%
OATP1B3 inhibitior	+	0.9269	92.69%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.5117	51.17%
P-glycoprotein inhibitior	+	0.7336	73.36%
P-glycoprotein substrate	+	0.6165	61.65%
CYP3A4 substrate	+	0.7366	73.66%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.7570	75.70%
CYP3A4 inhibition	-	0.9693	96.93%
CYP2C9 inhibition	-	0.9225	92.25%
CYP2C19 inhibition	-	0.8575	85.75%
CYP2D6 inhibition	-	0.8966	89.66%
CYP1A2 inhibition	-	0.9430	94.30%
CYP2C8 inhibition	+	0.7414	74.14%
CYP inhibitory promiscuity	-	0.8859	88.59%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6515	65.15%
Eye corrosion	-	0.9872	98.72%
Eye irritation	-	0.9026	90.26%
Skin irritation	-	0.7229	72.29%
Skin corrosion	-	0.9312	93.12%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8112	81.12%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.6798	67.98%
skin sensitisation	-	0.8732	87.32%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.8721	87.21%
Acute Oral Toxicity (c)	III	0.5860	58.60%
Estrogen receptor binding	+	0.7942	79.42%
Androgen receptor binding	+	0.7532	75.32%
Thyroid receptor binding	-	0.5604	56.04%
Glucocorticoid receptor binding	+	0.6170	61.70%
Aromatase binding	+	0.6481	64.81%
PPAR gamma	+	0.7246	72.46%
Honey bee toxicity	-	0.7181	71.81%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6393	63.93%
Fish aquatic toxicity	-	0.4189	41.89%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL220	P22303	Acetylcholinesterase	99.51%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.14%	96.09%
CHEMBL2179	P04062	Beta-glucocerebrosidase	97.88%	85.31%
CHEMBL237	P41145	Kappa opioid receptor	97.64%	98.10%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.43%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.05%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.75%	94.45%
CHEMBL3524	P56524	Histone deacetylase 4	95.50%	92.97%
CHEMBL2581	P07339	Cathepsin D	95.44%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	94.94%	95.93%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	94.04%	95.36%
CHEMBL2996	Q05655	Protein kinase C delta	94.04%	97.79%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	93.89%	91.03%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	93.79%	96.38%
CHEMBL1914	P06276	Butyrylcholinesterase	92.95%	95.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.74%	97.09%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	92.74%	95.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	92.34%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	91.62%	93.56%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	90.86%	97.29%
CHEMBL325	Q13547	Histone deacetylase 1	90.79%	95.92%
CHEMBL204	P00734	Thrombin	90.51%	96.01%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.42%	92.62%
CHEMBL4462	Q8IXJ6	NAD-dependent deacetylase sirtuin 2	90.42%	90.24%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.98%	95.89%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	89.55%	92.88%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	89.35%	96.21%
CHEMBL2094135	Q96BI3	Gamma-secretase	89.10%	98.05%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	89.09%	100.00%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	88.71%	92.86%
CHEMBL5255	O00206	Toll-like receptor 4	88.37%	92.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	87.68%	94.08%
CHEMBL5103	Q969S8	Histone deacetylase 10	87.15%	90.08%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.06%	96.61%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	86.51%	89.67%
CHEMBL5555	O00767	Acyl-CoA desaturase	86.07%	97.50%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	86.02%	94.23%
CHEMBL2514	O95665	Neurotensin receptor 2	85.94%	100.00%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.78%	95.17%
CHEMBL4816	Q9Y243	Serine/threonine-protein kinase AKT3	85.61%	96.28%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	85.46%	95.58%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.43%	89.05%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.38%	97.14%
CHEMBL3975	P09467	Fructose-1,6-bisphosphatase	85.18%	92.95%
CHEMBL3837	P07711	Cathepsin L	84.16%	96.61%
CHEMBL2959	Q08881	Tyrosine-protein kinase ITK/TSK	84.10%	95.00%
CHEMBL4370	P16662	UDP-glucuronosyltransferase 2B7	83.49%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.45%	95.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.22%	99.17%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.11%	97.33%
CHEMBL4835	P00338	L-lactate dehydrogenase A chain	83.04%	95.34%
CHEMBL2095194	P08709	Coagulation factor VII/tissue factor	82.86%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.76%	95.83%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.76%	100.00%
CHEMBL4072	P07858	Cathepsin B	82.29%	93.67%
CHEMBL5646	Q6L5J4	FML2_HUMAN	81.98%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.78%	90.71%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.51%	96.90%
CHEMBL1968	P07099	Epoxide hydrolase 1	80.47%	98.57%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.33%	93.04%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.08%	91.24%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 139587721
• LOTUS: LTS0243671
• wikiData: Q105347320