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

Details

• Internal ID: e53fd6c4-f3fb-41bd-af13-e877deb68b65
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2R,3R,4R,5R,6S)-6-[[(3S,4aS,6aR,6bR,8aR,12aS,14aS,14bS)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-hydroxy-3-[(2R,3R,4R,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-5-[(2S,3S,4R,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2C(=O)O)OC3CCC4(C(C3(C)C)CCC5(C4CC=C6C5(CCC7(C6CC(CC7)(C)C)C(=O)O)C)C)C)OC8C(C(C(CO8)O)O)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@H]([C@H]([C@H](O1)O[C@@H]2[C@H]([C@H]([C@H](O[C@H]2C(=O)O)O[C@H]3CC[C@@]4([C@@H](C3(C)C)CC[C@@]5([C@H]4CC=C6[C@@]5(CC[C@]7([C@H]6CC(CC7)(C)C)C(=O)O)C)C)C)O[C@H]8[C@H]([C@@H]([C@H](CO8)O)O)O)O)O)O)O
• InChI: InChI=1S/C47H74O17/c1-21-28(49)30(51)32(53)39(60-21)62-34-33(54)35(63-38-31(52)29(50)24(48)20-59-38)40(64-36(34)37(55)56)61-27-12-13-44(6)25(43(27,4)5)11-14-46(8)26(44)10-9-22-23-19-42(2,3)15-17-47(23,41(57)58)18-16-45(22,46)7/h9,21,23-36,38-40,48-54H,10-20H2,1-8H3,(H,55,56)(H,57,58)/t21-,23+,24+,25-,26+,27+,28+,29-,30-,31+,32-,33-,34-,35-,36-,38+,39-,40+,44-,45+,46-,47-/m1/s1
• InChI Key: VUCSYQUGUMWAFG-HXXJTREMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₄O₁₇
• Molecular Weight: 911.10 g/mol
• Exact Mass: 910.49260089 g/mol
• Topological Polar Surface Area (TPSA): 272.00 Ų
• XlogP: 3.00
• Atomic LogP (AlogP): 2.47
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8757	87.57%
Caco-2	-	0.8946	89.46%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8755	87.55%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.6844	68.44%
OATP1B3 inhibitior	-	0.2348	23.48%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5276	52.76%
BSEP inhibitior	+	0.7042	70.42%
P-glycoprotein inhibitior	+	0.7591	75.91%
P-glycoprotein substrate	-	0.6313	63.13%
CYP3A4 substrate	+	0.7251	72.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8798	87.98%
CYP3A4 inhibition	-	0.8622	86.22%
CYP2C9 inhibition	-	0.8630	86.30%
CYP2C19 inhibition	-	0.9344	93.44%
CYP2D6 inhibition	-	0.9426	94.26%
CYP1A2 inhibition	-	0.8847	88.47%
CYP2C8 inhibition	+	0.7284	72.84%
CYP inhibitory promiscuity	-	0.9755	97.55%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5992	59.92%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9070	90.70%
Skin irritation	-	0.5279	52.79%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6473	64.73%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.8875	88.75%
skin sensitisation	-	0.8703	87.03%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8941	89.41%
Acute Oral Toxicity (c)	III	0.5967	59.67%
Estrogen receptor binding	+	0.7860	78.60%
Androgen receptor binding	+	0.7260	72.60%
Thyroid receptor binding	-	0.6185	61.85%
Glucocorticoid receptor binding	+	0.7118	71.18%
Aromatase binding	+	0.6708	67.08%
PPAR gamma	+	0.7827	78.27%
Honey bee toxicity	-	0.6930	69.30%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5255	52.55%
Fish aquatic toxicity	+	0.9805	98.05%

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	97.14%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.39%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.44%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.34%	86.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.26%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.02%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.70%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.98%	97.09%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	85.41%	97.33%
CHEMBL2179	P04062	Beta-glucocerebrosidase	84.70%	85.31%
CHEMBL2581	P07339	Cathepsin D	84.54%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	83.73%	90.17%
CHEMBL5028	O14672	ADAM10	81.74%	97.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.82%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.64%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.58%	94.45%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	80.51%	89.44%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.46%	92.94%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.08%	91.07%

Plants that contains it

• Heptapleurum arboricola

Cross-Links

• PubChem: 162925868
• LOTUS: LTS0059491
• wikiData: Q105293212