(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-10-benzoyloxy-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid

Details

• Internal ID: a140c4e0-723b-4acf-854e-cbef870504ed
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-10-benzoyloxy-8-hydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-9-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C(CC2C1(C(CC3(C2=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)C(=O)O)O)OC7C(C(C(CO7)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)C)C)O)CO)(C)C)OC(=O)C9=CC=CC=C9
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1[C@@H](C(C[C@@H]2[C@]1([C@@H](C[C@@]3(C2=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O[C@H]7[C@@H]([C@H]([C@@H](CO7)O)O)O)O[C@H]8[C@@H]([C@H]([C@H]([C@H](O8)CO)O)O)O)C)C)C)O)CO)(C)C)OC(=O)C9=CC=CC=C9
• InChI: InChI=1S/C59H86O22/c1-10-27(2)49(72)81-47-46(80-50(73)28-14-12-11-13-15-28)54(3,4)22-30-29-16-17-34-56(7)20-19-36(55(5,6)33(56)18-21-57(34,8)58(29,9)23-35(63)59(30,47)26-61)76-53-45(79-52-41(68)39(66)38(65)32(24-60)75-52)43(42(69)44(78-53)48(70)71)77-51-40(67)37(64)31(62)25-74-51/h10-16,30-47,51-53,60-69H,17-26H2,1-9H3,(H,70,71)/b27-10-/t30-,31+,32+,33-,34+,35+,36-,37-,38-,39-,40+,41+,42-,43-,44-,45+,46-,47-,51-,52-,53+,56-,57+,58+,59-/m0/s1
• InChI Key: PQWRZZBQEIVFHI-ZPKYWXSPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₉H₈₆O₂₂
• Molecular Weight: 1147.30 g/mol
• Exact Mass: 1146.56107437 g/mol
• Topological Polar Surface Area (TPSA): 348.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 1.64
• H-Bond Acceptor: 21
• H-Bond Donor: 11
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8071	80.71%
Caco-2	-	0.8636	86.36%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8508	85.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7508	75.08%
OATP1B3 inhibitior	-	0.4332	43.32%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5776	57.76%
BSEP inhibitior	+	0.9699	96.99%
P-glycoprotein inhibitior	+	0.7461	74.61%
P-glycoprotein substrate	+	0.6011	60.11%
CYP3A4 substrate	+	0.7495	74.95%
CYP2C9 substrate	-	0.6044	60.44%
CYP2D6 substrate	-	0.8913	89.13%
CYP3A4 inhibition	-	0.6485	64.85%
CYP2C9 inhibition	-	0.8438	84.38%
CYP2C19 inhibition	-	0.8858	88.58%
CYP2D6 inhibition	-	0.9350	93.50%
CYP1A2 inhibition	-	0.8417	84.17%
CYP2C8 inhibition	+	0.8354	83.54%
CYP inhibitory promiscuity	-	0.9590	95.90%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6075	60.75%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.8979	89.79%
Skin irritation	-	0.6315	63.15%
Skin corrosion	-	0.9465	94.65%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7702	77.02%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.7966	79.66%
skin sensitisation	-	0.8967	89.67%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.7280	72.80%
Acute Oral Toxicity (c)	III	0.7534	75.34%
Estrogen receptor binding	+	0.6993	69.93%
Androgen receptor binding	+	0.7564	75.64%
Thyroid receptor binding	+	0.6523	65.23%
Glucocorticoid receptor binding	+	0.7966	79.66%
Aromatase binding	+	0.6340	63.40%
PPAR gamma	+	0.8130	81.30%
Honey bee toxicity	-	0.6375	63.75%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9824	98.24%

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	98.34%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	98.11%	90.17%
CHEMBL2581	P07339	Cathepsin D	94.85%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.55%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.80%	96.09%
CHEMBL4302	P08183	P-glycoprotein 1	92.44%	92.98%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.06%	95.56%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	91.08%	89.44%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	89.94%	89.67%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.95%	91.07%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	88.18%	91.65%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.52%	95.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.44%	99.17%
CHEMBL5028	O14672	ADAM10	87.34%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.65%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	86.57%	95.83%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.76%	99.23%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.65%	97.14%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.04%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.67%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	81.00%	95.93%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.66%	96.21%

Plants that contains it

• Barringtonia acutangula

Cross-Links

• PubChem: 11228621
• LOTUS: LTS0053344
• wikiData: Q105213512