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

Details

• Internal ID: d500685d-deeb-47cb-bf73-3e1d49dec467
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6S)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8,9-diacetyloxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-10-[(E)-3-phenylprop-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2S,3R,4S,5S)-4,5-dihydroxy-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC(=O)OC1CC2(C(=CCC3C2(CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)C(=O)O)O)OC6C(C(C(CO6)O)O)OC7C(C(C(CO7)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)C)C9C1(C(C(C(C9)(C)C)OC(=O)C=CC1=CC=CC=C1)OC(=O)C)CO)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@]2(C(=CC[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O[C@@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O[C@H]6[C@@H]([C@H]([C@H](CO6)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@H]9[C@@]1([C@H]([C@@H](C(C9)(C)C)OC(=O)/C=C/C1=CC=CC=C1)OC(=O)C)CO)C
• InChI: InChI=1S/C65H94O27/c1-29(68)84-40-24-64(9)32(33-23-60(3,4)53(54(85-30(2)69)65(33,40)28-67)88-41(72)18-15-31-13-11-10-12-14-31)16-17-38-62(7)21-20-39(61(5,6)37(62)19-22-63(38,64)8)87-59-52(92-57-47(78)45(76)44(75)36(25-66)86-57)49(48(79)50(90-59)55(80)81)89-58-51(43(74)35(71)27-83-58)91-56-46(77)42(73)34(70)26-82-56/h10-16,18,33-40,42-54,56-59,66-67,70-71,73-79H,17,19-28H2,1-9H3,(H,80,81)/b18-15+/t33-,34+,35-,36+,37-,38+,39-,40+,42-,43-,44-,45-,46+,47+,48-,49-,50-,51+,52+,53-,54-,56-,57-,58-,59-,62-,63+,64+,65-/m0/s1
• InChI Key: DTIRRQKBWVMPSW-DNKGIGMWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₆₅H₉₄O₂₇
• Molecular Weight: 1307.40 g/mol
• Exact Mass: 1306.59824772 g/mol
• Topological Polar Surface Area (TPSA): 413.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 0.13
• H-Bond Acceptor: 26
• H-Bond Donor: 12
• Rotatable Bonds: 16

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	-	0.8608	86.08%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8508	85.08%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7419	74.19%
OATP1B3 inhibitior	-	0.4332	43.32%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5776	57.76%
BSEP inhibitior	+	0.9798	97.98%
P-glycoprotein inhibitior	+	0.7440	74.40%
P-glycoprotein substrate	+	0.6308	63.08%
CYP3A4 substrate	+	0.7515	75.15%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8869	88.69%
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	+	0.8480	84.80%
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	-	0.8968	89.68%
Skin irritation	-	0.6315	63.15%
Skin corrosion	-	0.9465	94.65%
Ames mutagenesis	-	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7830	78.30%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	-	0.8000	80.00%
skin sensitisation	-	0.8967	89.67%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.6000	60.00%
Nephrotoxicity	-	0.8310	83.10%
Acute Oral Toxicity (c)	III	0.7534	75.34%
Estrogen receptor binding	+	0.6255	62.55%
Androgen receptor binding	+	0.7595	75.95%
Thyroid receptor binding	+	0.7253	72.53%
Glucocorticoid receptor binding	+	0.8069	80.69%
Aromatase binding	+	0.7019	70.19%
PPAR gamma	+	0.8185	81.85%
Honey bee toxicity	-	0.6282	62.82%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
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	99.27%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.25%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.25%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	94.91%	90.17%
CHEMBL2581	P07339	Cathepsin D	94.40%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.75%	95.56%
CHEMBL5028	O14672	ADAM10	91.63%	97.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.44%	94.45%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	89.00%	94.08%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	87.84%	89.44%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.58%	97.09%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.48%	95.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.88%	91.07%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	84.60%	95.83%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.33%	96.00%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.47%	89.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.94%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.40%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.62%	89.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.14%	93.00%

Plants that contains it

• Camellia sinensis

Cross-Links

• PubChem: 154497574
• LOTUS: LTS0190405
• wikiData: Q104988819