(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bS)-8-acetyloxy-8a-(hydroxymethyl)-5,5,6a,6b,11,11,14b-heptamethyl-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: 1b7b3a1a-9bfa-45f9-b098-01573d2389f8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bS)-8-acetyloxy-8a-(hydroxymethyl)-5,5,6a,6b,11,11,14b-heptamethyl-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)C)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(CC([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)C)C)C)OC(=O)C)CO)(C)C)OC(=O)/C(=C\C)/C
• InChI: InChI=1S/C53H80O18/c1-13-25(3)44(63)70-41-42(71-45(64)26(4)14-2)53(24-54)30(20-48(41,6)7)29-15-16-32-50(10)18-17-28(19-33(50)49(8,9)23-52(32,12)51(29,11)21-34(53)66-27(5)55)67-47-38(60)39(37(59)40(69-47)43(61)62)68-46-36(58)35(57)31(56)22-65-46/h13-15,28,30-42,46-47,54,56-60H,16-24H2,1-12H3,(H,61,62)/b25-13-,26-14-/t28-,30-,31-,32+,33+,34+,35-,36+,37-,38+,39-,40-,41-,42-,46-,47+,50+,51+,52+,53-/m0/s1
• InChI Key: JPSWEZAFQWCZAH-XQJRQZGZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₀O₁₈
• Molecular Weight: 1005.20 g/mol
• Exact Mass: 1004.53446570 g/mol
• Topological Polar Surface Area (TPSA): 275.00 Ų
• XlogP: 5.10
• Atomic LogP (AlogP): 4.04
• H-Bond Acceptor: 17
• H-Bond Donor: 7
• Rotatable Bonds: 11

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	-	0.8651	86.51%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8046	80.46%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.9457	94.57%
P-glycoprotein inhibitior	+	0.7534	75.34%
P-glycoprotein substrate	+	0.6361	63.61%
CYP3A4 substrate	+	0.7402	74.02%
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	+	0.7708	77.08%
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	-	0.9005	90.05%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.6748	67.48%
Human Ether-a-go-go-Related Gene inhibition	+	0.6802	68.02%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.6450	64.50%
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	+	0.4603	46.03%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7295	72.95%
Androgen receptor binding	+	0.7511	75.11%
Thyroid receptor binding	+	0.6030	60.30%
Glucocorticoid receptor binding	+	0.7912	79.12%
Aromatase binding	+	0.6285	62.85%
PPAR gamma	+	0.8289	82.89%
Honey bee toxicity	-	0.6685	66.85%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
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	98.96%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.39%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.28%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.56%	96.77%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	89.09%	94.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.24%	91.07%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.11%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.65%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.25%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.10%	89.00%
CHEMBL2581	P07339	Cathepsin D	86.08%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	85.35%	95.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.04%	95.50%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	84.61%	91.65%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.58%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.33%	97.25%
CHEMBL5028	O14672	ADAM10	83.95%	97.50%
CHEMBL4208	P20618	Proteasome component C5	83.13%	90.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.52%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.00%	96.90%
CHEMBL340	P08684	Cytochrome P450 3A4	80.88%	91.19%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.66%	99.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.51%	93.00%

Plants that contains it

• Polyspora chrysandra

Cross-Links

• PubChem: 162960610
• LOTUS: LTS0012058
• wikiData: Q105133150