(2R,3S,4S,5S,6S)-2-[[(2R,3S,5S,8S,9R,10S,12R,13R,14R,17R)-2,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2R)-6-methyl-2-[(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[[(2S,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 8fc38d0c-4a89-4c2e-bca6-587d3bbeaa7e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2R,3S,4S,5S,6S)-2-[[(2R,3S,5S,8S,9R,10S,12R,13R,14R,17R)-2,12-dihydroxy-4,4,8,10,14-pentamethyl-17-[(2R)-6-methyl-2-[(2S,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[[(2S,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-5-en-2-yl]-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(=CCCC(C)(C1CCC2(C1C(CC3C2(CCC4C3(CC(C(C4(C)C)OC5C(C(C(C(O5)CO)O)O)O)O)C)C)O)C)OC6C(C(C(C(O6)COC7C(C(C(CO7)O)O)O)O)O)O)C
• SMILES (Isomeric): CC(=CCC[C@](C)([C@@H]1CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@@]2(CC[C@H]4[C@]3(C[C@H]([C@H](C4(C)C)O[C@H]5[C@H]([C@H]([C@@H]([C@@H](O5)CO)O)O)O)O)C)C)O)C)O[C@H]6[C@@H]([C@H]([C@H]([C@@H](O6)CO[C@H]7[C@@H]([C@@H]([C@@H](CO7)O)O)O)O)O)O)C
• InChI: InChI=1S/C47H80O18/c1-21(2)10-9-13-47(8,65-42-38(59)35(56)33(54)27(63-42)20-61-40-36(57)31(52)25(51)19-60-40)22-11-14-46(7)30(22)23(49)16-29-44(5)17-24(50)39(43(3,4)28(44)12-15-45(29,46)6)64-41-37(58)34(55)32(53)26(18-48)62-41/h10,22-42,48-59H,9,11-20H2,1-8H3/t22-,23-,24-,25-,26+,27+,28-,29-,30+,31-,32-,33+,34+,35+,36-,37+,38-,39-,40+,41+,42+,44-,45+,46-,47-/m1/s1
• InChI Key: GELOPBLVWSJPGZ-QIKFCPSVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₈₀O₁₈
• Molecular Weight: 933.10 g/mol
• Exact Mass: 932.53446570 g/mol
• Topological Polar Surface Area (TPSA): 298.00 Ų
• XlogP: 1.00
• Atomic LogP (AlogP): -0.42
• H-Bond Acceptor: 18
• H-Bond Donor: 12
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.9032	90.32%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8260	82.60%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.6841	68.41%
P-glycoprotein inhibitior	+	0.7652	76.52%
P-glycoprotein substrate	-	0.5552	55.52%
CYP3A4 substrate	+	0.7235	72.35%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9502	95.02%
CYP2C9 inhibition	-	0.8671	86.71%
CYP2C19 inhibition	-	0.9036	90.36%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.9057	90.57%
CYP2C8 inhibition	+	0.6986	69.86%
CYP inhibitory promiscuity	-	0.9413	94.13%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6474	64.74%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9055	90.55%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.6024	60.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7902	79.02%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.6664	66.64%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.5714	57.14%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.7783	77.83%
Androgen receptor binding	+	0.7402	74.02%
Thyroid receptor binding	-	0.5251	52.51%
Glucocorticoid receptor binding	+	0.6903	69.03%
Aromatase binding	+	0.6279	62.79%
PPAR gamma	+	0.7792	77.92%
Honey bee toxicity	-	0.5715	57.15%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9172	91.72%

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	99.55%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.15%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.93%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.29%	95.93%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.66%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.90%	96.09%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	91.31%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.30%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.89%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.79%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.44%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.48%	95.89%
CHEMBL1951	P21397	Monoamine oxidase A	86.78%	91.49%
CHEMBL3714130	P46095	G-protein coupled receptor 6	86.60%	97.36%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	86.42%	91.24%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.94%	97.14%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.76%	95.83%
CHEMBL2996	Q05655	Protein kinase C delta	85.44%	97.79%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	85.23%	82.69%
CHEMBL2581	P07339	Cathepsin D	83.48%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.10%	91.07%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	82.90%	92.50%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.72%	96.90%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	82.10%	100.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.30%	92.62%
CHEMBL5028	O14672	ADAM10	81.05%	97.50%
CHEMBL259	P32245	Melanocortin receptor 4	81.05%	95.38%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 154496706
• LOTUS: LTS0023321
• wikiData: Q105007222