Esculentoside C

Details

• Internal ID: ce97c20d-aad9-4bbf-8d4f-06e5eb758813
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,4aR,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2-methoxycarbonyl-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)CO)OC6C(C(C(CO6)OC7C(C(C(C(O7)CO)O)O)O)O)O)C)C)C2C1)C)C(=O)O)C(=O)OC
• SMILES (Isomeric): C[C@@]1(CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H]([C@@]5(C)CO)O[C@H]6[C@@H]([C@H]([C@@H](CO6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)C)C)[C@@H]2C1)C)C(=O)O)C(=O)OC
• InChI: InChI=1S/C42H66O15/c1-37(36(52)53-6)13-15-42(35(50)51)16-14-40(4)21(22(42)17-37)7-8-26-38(2)11-10-27(39(3,20-44)25(38)9-12-41(26,40)5)57-33-31(48)29(46)24(19-54-33)56-34-32(49)30(47)28(45)23(18-43)55-34/h7,22-34,43-49H,8-20H2,1-6H3,(H,50,51)/t22-,23+,24+,25+,26+,27-,28+,29-,30-,31+,32+,33-,34-,37-,38-,39-,40+,41+,42-/m0/s1
• InChI Key: NMDFCFOQBAHNPV-RFTJXAPBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₆O₁₅
• Molecular Weight: 811.00 g/mol
• Exact Mass: 810.44017139 g/mol
• Topological Polar Surface Area (TPSA): 242.00 Ų
• XlogP: 1.80
• Atomic LogP (AlogP): 1.65
• H-Bond Acceptor: 14
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

• 65931-92-2
• ESCULENTOSIDEC
• (2S,4aR,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-9-(hydroxymethyl)-2-methoxycarbonyl-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• DTXSID801109702
• Phytolaccoside D (Esculentoside C)
• AKOS040763469
• HY-125121
• CS-0089380
• Q-100753
• 29-Methyl (3beta,4alpha,20beta)-3-[(4-O-beta-D-glucopyranosyl-beta-D-xylopyranosyl)oxy]-23-hydroxyolean-12-ene-28,29-dioate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6450	64.50%
Caco-2	-	0.8803	88.03%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8410	84.10%
OATP2B1 inhibitior	-	0.8759	87.59%
OATP1B1 inhibitior	+	0.7712	77.12%
OATP1B3 inhibitior	-	0.2591	25.91%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5021	50.21%
BSEP inhibitior	+	0.8209	82.09%
P-glycoprotein inhibitior	+	0.7522	75.22%
P-glycoprotein substrate	-	0.5751	57.51%
CYP3A4 substrate	+	0.7324	73.24%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8825	88.25%
CYP3A4 inhibition	-	0.9325	93.25%
CYP2C9 inhibition	-	0.9274	92.74%
CYP2C19 inhibition	-	0.9129	91.29%
CYP2D6 inhibition	-	0.9549	95.49%
CYP1A2 inhibition	-	0.8851	88.51%
CYP2C8 inhibition	+	0.7414	74.14%
CYP inhibitory promiscuity	-	0.9658	96.58%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6068	60.68%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.9121	91.21%
Skin irritation	-	0.6260	62.60%
Skin corrosion	-	0.9468	94.68%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7737	77.37%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.7934	79.34%
skin sensitisation	-	0.9199	91.99%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.5609	56.09%
Acute Oral Toxicity (c)	III	0.6420	64.20%
Estrogen receptor binding	+	0.7390	73.90%
Androgen receptor binding	+	0.7346	73.46%
Thyroid receptor binding	-	0.6223	62.23%
Glucocorticoid receptor binding	+	0.6595	65.95%
Aromatase binding	+	0.6476	64.76%
PPAR gamma	+	0.7408	74.08%
Honey bee toxicity	-	0.7019	70.19%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9298	92.98%

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	98.84%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.23%	94.45%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	93.04%	95.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.13%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.54%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.51%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	89.04%	83.82%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.78%	96.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.87%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.74%	99.17%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.83%	94.33%
CHEMBL5028	O14672	ADAM10	85.50%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.58%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.12%	99.23%
CHEMBL5255	O00206	Toll-like receptor 4	83.88%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.17%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	83.06%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.70%	91.07%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.33%	97.33%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.83%	86.33%
CHEMBL2581	P07339	Cathepsin D	80.69%	98.95%

Plants that contains it

• Phytolacca acinosa
• Phytolacca americana

Cross-Links

• PubChem: 10724099
• NPASS: NPC304068