[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-5-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-6a,6b,9,9,12a-pentamethyl-2-methylidene-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate

Details

• Internal ID: 50f07a03-6522-46f0-9ab8-65c7cba12a2e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2S,3R,4S,5S)-5-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-6a,6b,9,9,12a-pentamethyl-2-methylidene-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(COC2OC3CCC4(C(C3(C)C)CCC5(C4CC=C6C5(CCC7(C6CC(=C)CC7)C(=O)OC8C(C(C(C(O8)CO)O)O)O)C)C)C)O)OC9C(C(C(C(O9)CO)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](CO[C@H]2O[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(=C)CC7)C(=O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)C)C)O)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O)O
• InChI: InChI=1S/C52H82O21/c1-22-10-15-52(47(65)73-45-40(64)37(61)34(58)28(20-54)69-45)17-16-50(6)24(25(52)18-22)8-9-30-49(5)13-12-31(48(3,4)29(49)11-14-51(30,50)7)70-46-42(72-43-38(62)35(59)32(56)23(2)67-43)41(26(55)21-66-46)71-44-39(63)36(60)33(57)27(19-53)68-44/h8,23,25-46,53-64H,1,9-21H2,2-7H3/t23-,25-,26-,27+,28+,29-,30+,31-,32-,33+,34+,35+,36-,37-,38+,39+,40+,41-,42+,43-,44-,45-,46-,49-,50+,51+,52-/m0/s1
• InChI Key: IFKVQLFRSXXGJD-WXGBTCDBSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₈₂O₂₁
• Molecular Weight: 1043.20 g/mol
• Exact Mass: 1042.53485962 g/mol
• Topological Polar Surface Area (TPSA): 334.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): -0.84
• H-Bond Acceptor: 21
• H-Bond Donor: 12
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7709	77.09%
Caco-2	-	0.8805	88.05%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8311	83.11%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7473	74.73%
OATP1B3 inhibitior	-	0.5076	50.76%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	+	0.9041	90.41%
P-glycoprotein inhibitior	+	0.7462	74.62%
P-glycoprotein substrate	-	0.5760	57.60%
CYP3A4 substrate	+	0.7311	73.11%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.8823	88.23%
CYP2C9 inhibition	-	0.8494	84.94%
CYP2C19 inhibition	-	0.8753	87.53%
CYP2D6 inhibition	-	0.9408	94.08%
CYP1A2 inhibition	-	0.8738	87.38%
CYP2C8 inhibition	+	0.7325	73.25%
CYP inhibitory promiscuity	-	0.9674	96.74%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6456	64.56%
Eye corrosion	-	0.9885	98.85%
Eye irritation	-	0.9026	90.26%
Skin irritation	-	0.5881	58.81%
Skin corrosion	-	0.9420	94.20%
Ames mutagenesis	-	0.6970	69.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7688	76.88%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.9250	92.50%
skin sensitisation	-	0.8777	87.77%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	-	0.9254	92.54%
Acute Oral Toxicity (c)	III	0.7897	78.97%
Estrogen receptor binding	+	0.7891	78.91%
Androgen receptor binding	+	0.7384	73.84%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7277	72.77%
Aromatase binding	+	0.6358	63.58%
PPAR gamma	+	0.7966	79.66%
Honey bee toxicity	-	0.6556	65.56%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5145	51.45%
Fish aquatic toxicity	+	0.9697	96.97%

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	98.44%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.38%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.36%	98.95%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.74%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.45%	86.33%
CHEMBL237	P41145	Kappa opioid receptor	90.07%	98.10%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.82%	95.56%
CHEMBL233	P35372	Mu opioid receptor	88.82%	97.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.92%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.31%	89.00%
CHEMBL5028	O14672	ADAM10	85.21%	97.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.59%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.42%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	82.48%	91.19%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.28%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.20%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.69%	99.17%
CHEMBL5255	O00206	Toll-like receptor 4	81.22%	92.50%

Plants that contains it

• Debia ovatifolia
• Guaiacum officinale
• Larrea tridentata

Cross-Links

• PubChem: 101589132
• LOTUS: LTS0233854
• wikiData: Q105112226