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

Details

• Internal ID: af416ef5-c3ef-45ed-aa86-06b8ff333115
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4aS,5S,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8-acetyloxy-5,8a-bis(hydroxymethyl)-5,6a,6b,11,11,14b-hexamethyl-9,10-bis[[(Z)-2-methylbut-2-enoyl]oxy]-1,2,3,4,4a,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,5-dihydroxy-4-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(CC5C(CC4(C3(CC2OC(=O)C)C)C)(C)CO)OC6C(C(C(C(O6)C(=O)O)O)OC7C(C(C(CO7)O)O)O)O)C)CO)OC(=O)C(=CC)C
• 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(C[C@]([C@@H]5[C@@]4(CC[C@@H](C5)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)(C)CO)C)C)OC(=O)C)CO)(C)C)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C53H80O19/c1-12-25(3)44(64)71-41-42(72-45(65)26(4)13-2)53(24-55)30(19-48(41,6)7)29-14-15-32-50(9)17-16-28(18-33(50)49(8,23-54)22-52(32,11)51(29,10)20-34(53)67-27(5)56)68-47-38(61)39(37(60)40(70-47)43(62)63)69-46-36(59)35(58)31(57)21-66-46/h12-14,28,30-42,46-47,54-55,57-61H,15-24H2,1-11H3,(H,62,63)/b25-12-,26-13-/t28-,30-,31-,32+,33+,34+,35-,36+,37-,38+,39-,40-,41-,42-,46-,47+,49+,50+,51+,52+,53-/m0/s1
• InChI Key: WWTKUHRYILFDAY-WPEGDTBMSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₀O₁₉
• Molecular Weight: 1021.20 g/mol
• Exact Mass: 1020.52938032 g/mol
• Topological Polar Surface Area (TPSA): 295.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.01
• H-Bond Acceptor: 18
• H-Bond Donor: 8
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7601	76.01%
Caco-2	-	0.8659	86.59%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7966	79.66%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.9588	95.88%
P-glycoprotein inhibitior	+	0.7517	75.17%
P-glycoprotein substrate	+	0.6544	65.44%
CYP3A4 substrate	+	0.7433	74.33%
CYP2C9 substrate	-	0.7978	79.78%
CYP2D6 substrate	-	0.8976	89.76%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.8704	87.04%
CYP2C19 inhibition	-	0.9216	92.16%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.9009	90.09%
CYP2C8 inhibition	+	0.7809	78.09%
CYP inhibitory promiscuity	-	0.9733	97.33%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6024	60.24%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9001	90.01%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.6948	69.48%
Human Ether-a-go-go-Related Gene inhibition	+	0.7089	70.89%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6325	63.25%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.5432	54.32%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7330	73.30%
Androgen receptor binding	+	0.7551	75.51%
Thyroid receptor binding	+	0.6166	61.66%
Glucocorticoid receptor binding	+	0.7887	78.87%
Aromatase binding	+	0.6241	62.41%
PPAR gamma	+	0.8316	83.16%
Honey bee toxicity	-	0.6714	67.14%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9585	95.85%

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	98.46%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.10%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.67%	96.09%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	91.56%	95.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.36%	96.77%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.04%	91.07%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	88.81%	94.33%
CHEMBL2581	P07339	Cathepsin D	88.34%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.53%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.09%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.85%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.87%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	85.31%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.04%	97.09%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.01%	97.28%
CHEMBL5028	O14672	ADAM10	83.95%	97.50%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	82.31%	89.34%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.86%	93.00%
CHEMBL4208	P20618	Proteasome component C5	81.77%	90.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.64%	97.25%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.69%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	80.44%	91.19%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.32%	96.90%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.23%	95.50%

Plants that contains it

• Polyspora chrysandra

Cross-Links

• PubChem: 163047100
• LOTUS: LTS0114083
• wikiData: Q105314310