(2S,3R,4S,5S,6R)-2-{[(2S)-2-[(1S,3aR,9aR,11S,11aS)-7-{[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-11-hydroxy-3a,6,6,9a-tetramethyl-tetradecahydrocyclopenta[a]phenanthren-1-yl]-4,6-dimethylhept-5-en-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: e9b6da4c-81b1-4e6c-b764-50cb93d6c271
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(10R,12S,13S,14R,17S)-17-[(2S)-4,6-dimethyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhept-5-en-2-yl]-12-hydroxy-4,4,10,14-tetramethyl-1,2,3,5,6,7,8,9,11,12,13,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(CC(C)(C1CCC2(C1C(CC3C2CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)C)O)C)OC7C(C(C(C(O7)CO)O)O)O)C=C(C)C
• SMILES (Isomeric): CC(C[C@@](C)([C@H]1CC[C@]2([C@H]1[C@H](CC3C2CCC4[C@@]3(CCC(C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)O)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C=C(C)C
• InChI: InChI=1S/C48H82O18/c1-21(2)15-22(3)17-48(8,66-43-40(60)37(57)34(54)28(19-50)62-43)24-11-13-47(7)23-9-10-30-45(4,5)31(12-14-46(30,6)25(23)16-26(52)32(24)47)64-44-41(38(58)35(55)29(20-51)63-44)65-42-39(59)36(56)33(53)27(18-49)61-42/h15,22-44,49-60H,9-14,16-20H2,1-8H3/t22?,23?,24-,25?,26-,27+,28+,29+,30?,31?,32+,33+,34+,35+,36-,37-,38-,39+,40+,41+,42-,43-,44-,46+,47+,48-/m0/s1
• InChI Key: IRBVCFDYIGGFFY-ADSMOORZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₈₂O₁₈
• Molecular Weight: 947.20 g/mol
• Exact Mass: 946.55011576 g/mol
• Topological Polar Surface Area (TPSA): 298.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): -0.17
• H-Bond Acceptor: 18
• H-Bond Donor: 12
• Rotatable Bonds: 13

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	-	0.9006	90.06%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8308	83.08%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.7050	70.50%
P-glycoprotein inhibitior	+	0.7609	76.09%
P-glycoprotein substrate	-	0.6083	60.83%
CYP3A4 substrate	+	0.7299	72.99%
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	+	0.6365	63.65%
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	-	0.9054	90.54%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8450	84.50%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5739	57.39%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.8289	82.89%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.8075	80.75%
Androgen receptor binding	+	0.7391	73.91%
Thyroid receptor binding	-	0.5302	53.02%
Glucocorticoid receptor binding	+	0.6966	69.66%
Aromatase binding	+	0.6729	67.29%
PPAR gamma	+	0.7826	78.26%
Honey bee toxicity	-	0.5203	52.03%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
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
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.08%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.10%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.00%	97.25%
CHEMBL226	P30542	Adenosine A1 receptor	92.26%	95.93%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.26%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	92.24%	96.21%
CHEMBL2581	P07339	Cathepsin D	92.05%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	92.01%	97.79%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	91.75%	95.58%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.98%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.46%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.40%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.62%	85.14%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	88.93%	96.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.33%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.77%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.69%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.58%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.61%	97.14%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	84.82%	92.86%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	84.71%	97.29%
CHEMBL2179	P04062	Beta-glucocerebrosidase	84.70%	85.31%
CHEMBL206	P03372	Estrogen receptor alpha	84.09%	97.64%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.95%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	83.16%	95.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.71%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.70%	97.36%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	81.75%	96.09%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.72%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.68%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.49%	92.62%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.01%	95.50%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 3036963
• NPASS: NPC269298