Esculentoside B

Details

• Internal ID: a2e676f3-600d-4d66-8928-a5259eb6e63c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,4aR,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-11-hydroxy-9-(hydroxymethyl)-2-methoxycarbonyl-2,6a,6b,9,12a-pentamethyl-10-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-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(CC(C(C5(C)CO)OC6C(C(C(CO6)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(C[C@@H]([C@@H]([C@@]5(C)CO)O[C@H]6[C@@H]([C@H]([C@@H](CO6)O)O)O)O)C)C)[C@@H]2C1)C)C(=O)O)C(=O)OC
• InChI: InChI=1S/C36H56O11/c1-31(30(44)45-6)11-13-36(29(42)43)14-12-34(4)19(20(36)15-31)7-8-24-32(2)16-21(38)27(47-28-26(41)25(40)22(39)17-46-28)33(3,18-37)23(32)9-10-35(24,34)5/h7,20-28,37-41H,8-18H2,1-6H3,(H,42,43)/t20-,21-,22+,23+,24+,25-,26+,27-,28-,31-,32-,33-,34+,35+,36-/m0/s1
• InChI Key: SFZVDNKTWPZIJG-ACNZYQHGSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₆O₁₁
• Molecular Weight: 664.80 g/mol
• Exact Mass: 664.38226260 g/mol
• Topological Polar Surface Area (TPSA): 183.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.79
• H-Bond Acceptor: 10
• H-Bond Donor: 6
• Rotatable Bonds: 5

Synonyms

• Phytolaccoside B
• 60820-94-2
• CHEBI:8194
• CHEMBL258392
• (2S,4aR,6aR,6aS,6bR,8aR,9R,10R,11S,12aR,14bS)-11-hydroxy-9-(hydroxymethyl)-2-methoxycarbonyl-2,6a,6b,9,12a-pentamethyl-10-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• C36-H56-O11
• DTXSID401317034
• Phytolaccoside B (Esculentoside B)
• BDBM50231813
• AKOS040761708
• 3-O-beta-D-xylopiranosylphytolaccagenin
• C08968
• Q-100700
• Q27107907
• (2S,4aR,6aS,6bR,8aR,9R,10R,11S,12aR,12bR,14bS)-11-hydroxy-9-(hydroxymethyl)-2-(methoxycarbonyl)-2,6a,6b,9,12a-pentamethyl-10-((2S,3R,4S,5R)-3,4,5-trihydroxy-tetrahydro-2H-pyran-2-yloxy)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7353	73.53%
Caco-2	-	0.8531	85.31%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8207	82.07%
OATP2B1 inhibitior	-	0.5884	58.84%
OATP1B1 inhibitior	+	0.8112	81.12%
OATP1B3 inhibitior	+	0.7945	79.45%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6021	60.21%
BSEP inhibitior	-	0.5549	55.49%
P-glycoprotein inhibitior	+	0.7352	73.52%
P-glycoprotein substrate	+	0.5187	51.87%
CYP3A4 substrate	+	0.7058	70.58%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8825	88.25%
CYP3A4 inhibition	-	0.8380	83.80%
CYP2C9 inhibition	-	0.9140	91.40%
CYP2C19 inhibition	-	0.8827	88.27%
CYP2D6 inhibition	-	0.9482	94.82%
CYP1A2 inhibition	-	0.8447	84.47%
CYP2C8 inhibition	+	0.6927	69.27%
CYP inhibitory promiscuity	-	0.9734	97.34%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6867	68.67%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9243	92.43%
Skin irritation	-	0.5947	59.47%
Skin corrosion	-	0.9473	94.73%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6571	65.71%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.7559	75.59%
skin sensitisation	-	0.9183	91.83%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	+	0.7838	78.38%
Acute Oral Toxicity (c)	III	0.6651	66.51%
Estrogen receptor binding	+	0.6468	64.68%
Androgen receptor binding	+	0.7396	73.96%
Thyroid receptor binding	-	0.5825	58.25%
Glucocorticoid receptor binding	+	0.6535	65.35%
Aromatase binding	+	0.6652	66.52%
PPAR gamma	+	0.6421	64.21%
Honey bee toxicity	-	0.7957	79.57%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9118	91.18%

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	99.00%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	95.69%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.57%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	93.90%	95.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.16%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.42%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.21%	96.77%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.62%	91.07%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.14%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.30%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	87.31%	94.33%
CHEMBL340	P08684	Cytochrome P450 3A4	85.98%	91.19%
CHEMBL2916	O14746	Telomerase reverse transcriptase	85.82%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.38%	95.89%
CHEMBL5028	O14672	ADAM10	82.58%	97.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.02%	95.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.85%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.05%	93.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.47%	96.90%

Plants that contains it

• Allium nutans
• Dalea gattingeri
• Phytolacca acinosa
• Phytolacca americana
• Phytolacca dodecandra
• Phytolacca tetramera
• Phytolacca thyrsiflora
• Solanum incanum
• Stachys mucronata

Cross-Links

• PubChem: 441939
• NPASS: NPC127853
• ChEMBL: CHEMBL258392
• LOTUS: LTS0196328
• wikiData: Q27107907